NP-MRD: Showing NP-Card for Chlorogenic acid (NP0000578)

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Record Information

Version

1.0

Created at

2006-05-22 15:12:37 UTC

Updated at

2024-04-19 10:04:04 UTC

NP-MRD ID

NP0000578

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chlorogenic acid

Description

Chlorogenic acid is an ester of caffeic acid and quinic acid. Chlorogenic acid is the major polyphenolic compound in coffee, isolated from the leaves and fruits of dicotyledonous plants. This compound, long known as an antioxidant, also slows the release of glucose into the bloodstream after a meal. Coffee is a complex mixture of chemicals that provides significant amounts of chlorogenic acid. The chlorogenic acid content of a 200 ml (7-oz) cup of coffee has been reported to range from 70-350 mg, which would provide about 35-175 mg of caffeic acid. The results of epidemiological research suggest that coffee consumption may help prevent several chronic diseases, including type 2 diabetes mellitus, Parkinson's disease and liver disease (cirrhosis and hepatocellular carcinoma). Most prospective cohort studies have not found coffee consumption to be associated with significantly increased cardiovascular disease risk. However, coffee consumption is associated with increases in several cardiovascular disease risk factors, including blood pressure and plasma homocysteine. At present, there is little evidence that coffee consumption increases the risk of cancer. (PMID: 16507475 , 17368041 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0003164
     RDKit          3D
Chlorogenic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.0245    2.8621    0.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    1.7104    0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    1.3032    0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    0.1023    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4022   -0.3784    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065   -1.6760   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8704   -2.1748   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9512   -1.3939   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2387   -1.8553   -0.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7415   -0.0904    0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7906    0.7383    0.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4548    0.4160    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    0.8569    0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.2783    0.2455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7784    0.4622    1.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395   -0.7813    0.7452 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3228   -1.2279    1.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096   -1.7968    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -2.8602    1.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3874   -1.6206   -0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2570   -0.5128   -0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2087    0.9298   -0.9241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7313    1.8030    0.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292    1.2813   -1.0965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7356    2.5838   -1.6485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    2.0052    0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2154   -0.5679   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7593   -2.2998   -0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0698   -3.2014   -0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4657   -2.7820   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7527    0.4157    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343    1.4440    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    2.3466    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    1.0323    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0416    0.1085    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6657   -0.4836    2.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161   -2.2231   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189   -0.7963   -0.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231   -1.1165   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7279    1.0272   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5480    1.4646    0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278    0.5898   -1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463    3.0775   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 12  5  1  0
 24 14  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  1
 15 34  1  0
 15 35  1  0
 17 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  6
 23 41  1  0
 24 42  1  6
 25 43  1  0
M  END


  Mrv1652309272007282D          

 25 26  0  0  1  0            999 V2000
   16.9133  -14.7737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.6278  -15.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6278  -16.0047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.9133  -16.4170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1987  -16.0047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1987  -15.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3425  -16.4170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0570  -16.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7605  -16.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4751  -16.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0570  -15.1859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1897  -16.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9043  -16.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1897  -17.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6188  -16.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9043  -17.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6188  -17.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3337  -17.6539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3256  -14.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9133  -17.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4839  -16.4170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5009  -14.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9133  -13.3443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6765  -14.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9043  -18.4788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  1 19  1  6  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  3  7  1  1  0  0  0
  5  4  1  0  0  0  0
  4 20  1  6  0  0  0
  6  5  1  0  0  0  0
  5 21  1  6  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11  8  2  0  0  0  0
 10  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  2  0  0  0  0
 15 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
  1 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 16 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1

> <INCHI_KEY>
CWVRJTMFETXNAD-JUHZACGLSA-N

> <FORMULA>
C16H18O9

> <MOLECULAR_WEIGHT>
354.3087

> <EXACT_MASS>
354.095082174

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.416314108940696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-0.26852975799999984

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.20854914523281

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3338531471838464

> <JCHEM_PKA_STRONGEST_BASIC>
-3.231823980915407

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
83.23470000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorogenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003164
     RDKit          3D
Chlorogenic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.0245    2.8621    0.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    1.7104    0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    1.3032    0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    0.1023    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4022   -0.3784    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065   -1.6760   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8704   -2.1748   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9512   -1.3939   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2387   -1.8553   -0.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7415   -0.0904    0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7906    0.7383    0.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4548    0.4160    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    0.8569    0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.2783    0.2455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7784    0.4622    1.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395   -0.7813    0.7452 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3228   -1.2279    1.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096   -1.7968    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -2.8602    1.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3874   -1.6206   -0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2570   -0.5128   -0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2087    0.9298   -0.9241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7313    1.8030    0.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292    1.2813   -1.0965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7356    2.5838   -1.6485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    2.0052    0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2154   -0.5679   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7593   -2.2998   -0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0698   -3.2014   -0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4657   -2.7820   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7527    0.4157    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343    1.4440    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    2.3466    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    1.0323    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0416    0.1085    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6657   -0.4836    2.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161   -2.2231   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189   -0.7963   -0.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231   -1.1165   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7279    1.0272   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5480    1.4646    0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278    0.5898   -1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463    3.0775   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 12  5  1  0
 24 14  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  1
 15 34  1  0
 15 35  1  0
 17 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  6
 23 41  1  0
 24 42  1  6
 25 43  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      31.571 -27.578   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.905 -28.347   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.905 -29.875   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.571 -30.645   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.238 -29.875   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.238 -28.347   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      34.239 -30.645   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      35.573 -29.875   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      36.886 -30.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.220 -29.875   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      35.573 -28.347   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      39.554 -30.645   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.888 -29.875   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      39.554 -32.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      42.222 -30.645   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      40.888 -32.954   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      42.222 -32.184   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      43.556 -32.954   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      32.341 -26.243   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      31.571 -32.184   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      28.903 -30.645   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      30.802 -26.243   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      31.571 -24.909   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      29.263 -26.243   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      40.888 -34.494   0.000  0.00  0.00           O+0
CONECT    1    2    6   19   22                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   21                                                  
CONECT    6    1    5                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9   12                                                       
CONECT   11    8                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   17   25                                                  
CONECT   17   15   16   18                                                  
CONECT   18   17                                                            
CONECT   19    1                                                            
CONECT   20    4                                                            
CONECT   21    5                                                            
CONECT   22    1   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   16                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0003164
HETATM    1  O1  UNL     1      -0.024   2.862   0.939  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.317   1.710   0.566  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.719   1.303   0.525  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.048   0.102   0.134  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.402  -0.378   0.065  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.606  -1.676  -0.368  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.870  -2.175  -0.450  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.951  -1.394  -0.104  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.239  -1.855  -0.171  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.741  -0.090   0.331  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.791   0.738   0.692  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.455   0.416   0.414  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.717   0.857   0.197  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.084   1.278   0.245  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.778   0.462   1.280  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.439  -0.781   0.745  1.00  0.00           C  
HETATM   17  O5  UNL     1      -4.323  -1.228   1.725  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.410  -1.797   0.531  1.00  0.00           C  
HETATM   19  O6  UNL     1      -2.432  -2.860   1.193  1.00  0.00           O  
HETATM   20  O7  UNL     1      -1.387  -1.621  -0.397  1.00  0.00           O  
HETATM   21  C14 UNL     1      -4.257  -0.513  -0.495  1.00  0.00           C  
HETATM   22  C15 UNL     1      -4.209   0.930  -0.924  1.00  0.00           C  
HETATM   23  O8  UNL     1      -4.731   1.803   0.002  1.00  0.00           O  
HETATM   24  C16 UNL     1      -2.729   1.281  -1.096  1.00  0.00           C  
HETATM   25  O9  UNL     1      -2.736   2.584  -1.649  1.00  0.00           O  
HETATM   26  H1  UNL     1       2.464   2.005   0.821  1.00  0.00           H  
HETATM   27  H2  UNL     1       1.215  -0.568  -0.156  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.759  -2.300  -0.644  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.070  -3.201  -0.791  1.00  0.00           H  
HETATM   30  H5  UNL     1       7.466  -2.782  -0.475  1.00  0.00           H  
HETATM   31  H6  UNL     1       7.753   0.416   0.649  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.334   1.444   0.760  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.088   2.347   0.614  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.540   1.032   1.860  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.042   0.108   2.060  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.666  -0.484   2.291  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.416  -2.223  -1.217  1.00  0.00           H  
HETATM   38  H13 UNL     1      -5.319  -0.796  -0.386  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.823  -1.116  -1.316  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.728   1.027  -1.881  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.548   1.465   0.440  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.228   0.590  -1.800  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.546   3.078  -1.391  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   26
CONECT    4    5   27
CONECT    5    6    6   12
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   10
CONECT    9   30
CONECT   10   11   12   12
CONECT   11   31
CONECT   12   32
CONECT   13   14
CONECT   14   15   24   33
CONECT   15   16   34   35
CONECT   16   17   18   21
CONECT   17   36
CONECT   18   19   19   20
CONECT   20   37
CONECT   21   22   38   39
CONECT   22   23   24   40
CONECT   23   41
CONECT   24   25   42
CONECT   25   43
END

HMDB0003164
     RDKit          3D
Chlorogenic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.0245    2.8621    0.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    1.7104    0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    1.3032    0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    0.1023    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4022   -0.3784    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065   -1.6760   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8704   -2.1748   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9512   -1.3939   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2387   -1.8553   -0.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7415   -0.0904    0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7906    0.7383    0.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4548    0.4160    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    0.8569    0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.2783    0.2455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7784    0.4622    1.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395   -0.7813    0.7452 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3228   -1.2279    1.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096   -1.7968    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -2.8602    1.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3874   -1.6206   -0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2570   -0.5128   -0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2087    0.9298   -0.9241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7313    1.8030    0.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292    1.2813   -1.0965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7356    2.5838   -1.6485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    2.0052    0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2154   -0.5679   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7593   -2.2998   -0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0698   -3.2014   -0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4657   -2.7820   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7527    0.4157    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343    1.4440    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    2.3466    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    1.0323    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0416    0.1085    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6657   -0.4836    2.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161   -2.2231   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189   -0.7963   -0.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231   -1.1165   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7279    1.0272   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5480    1.4646    0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278    0.5898   -1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463    3.0775   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 12  5  1  0
 24 14  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  1
 15 34  1  0
 15 35  1  0
 17 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  6
 23 41  1  0
 24 42  1  6
 25 43  1  0
M  END

View in JSmol

Synonyms

Value	Source
3-(3,4-Dihydroxycinnamoyl)quinic acid	ChEBI
3-Caffeoylquinic acid	ChEBI
3-O-Caffeoylquinic acid	ChEBI
5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid	ChEBI
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid	ChEBI
Caffeoyl quinic acid	ChEBI
Chlorogenate	ChEBI
trans-5-O-Caffeoyl-D-quinate	ChEBI
3-(3,4-Dihydroxycinnamoyl)quinate	Generator
3-Caffeoylquinate	Generator
3-O-Caffeoylquinate	Generator
5-O-(3,4-Dihydroxycinnamoyl)-L-quinate	Generator
[1S-(1a,3b,4a,5a)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylate	Generator
[1S-(1a,3b,4a,5a)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid	Generator
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylate	Generator
[1S-(1Α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylate	Generator
[1S-(1Α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid	Generator
Caffeoyl quinate	Generator
trans-5-O-Caffeoyl-D-quinic acid	Generator
3-trans-Caffeoylquinic acid	HMDB
Heriguard	HMDB
Hlorogenate	HMDB
Hlorogenic acid	HMDB
Acid, chlorogenic	HMDB
3 Caffeoylquinic acid	HMDB
Acid, 3-caffeoylquinic	HMDB
(-)-5-Caffeoyl quinic acid	HMDB
5-O-(e)-Caffeoylquinic acid	HMDB
5-trans-O-Caffeoylquinic acid	HMDB
trans-3-O-Caffeoylquinic acid	HMDB
trans-Caffeic acid 5-O-D-quinate	HMDB
trans-Chlorogenic acid	HMDB
3-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid	HMDB
5-Chlorogenic acid	HMDB
Caffeoylquinic acid	HMDB

Chemical Formula

C₁₆H₁₈O₉

Average Mass

354.3087 Da

Monoisotopic Mass

354.09508 Da

IUPAC Name

(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

Traditional Name

chlorogenic acid

CAS Registry Number

327-97-9

SMILES

O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O

InChI Identifier

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1

InChI Key

CWVRJTMFETXNAD-JUHZACGLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 700 MHz, CD3OD, experimental)	jaewoo.choi@oregonstate.edu	Not Available	Not Available	2023-06-28	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2023-06-27	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2023-06-27	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2023-06-27	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2023-06-27	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2023-06-27	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	jtkp6n@mail.missouri.edu	Not Available	Not Available	2023-02-24	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	jtkp6n@mail.missouri.edu	Not Available	Not Available	2023-02-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.13 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.13 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800.148940889 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800.148940889 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201.216488466 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	FooDB
Acacia nilotica	KNApSAcK Database	22123792
Acer truncatum	LOTUS Database	35616633
Achillea millefolium	KNApSAcK Database	22123792
Achyrocline alata	LOTUS Database	35616633
Achyrocline flaccida	LOTUS Database	35616633
Achyrocline satureioides	LOTUS Database	35616633
Actinidia chinensis	FooDB	PHENOL EXPLORER
Adiantum caudatum	Plant	KNApSAcK
Adina racemosa	KNApSAcK Database	22123792
Agaricus bisporus	FooDB	FooDB
Agave	FooDB	FooDB
Ageratina adenophora	LOTUS Database	35616633
Ajania fruticulosa	LOTUS Database	35616633
Aleuritopteris formosana	LOTUS Database	35616633
Alibertia sessilis	LOTUS Database	35616633
Allium ampeloprasum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	FooDB
Allium cepa L.	FooDB	FooDB
Allium fistulosum	FooDB	FooDB
Allium obliquum	Plant	KNApSAcK
Allium sativum	KNApSAcK Database	22123792
Allium schoenoprasum	FooDB	FooDB
Allium tuberosum	FooDB	FooDB
Aloysia triphylla	FooDB	FooDB
Amaranthus	FooDB	FooDB
Ambrosia artemisiifolia	LOTUS Database	35616633
Amelanchier alnifolia	FooDB	FooDB
Amelanchier sanguinea	LOTUS Database	35616633
Anacardium occidentale	FooDB	FooDB
Ananas comosus	FooDB	FooDB
Andrographis paniculata	KNApSAcK Database	22123792
Anethum foeniculum	Plant	KNApSAcK
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Angelica furcijuga KITAGAWA	KNApSAcK Database	22123792
Angelica keiskei	FooDB	FooDB
Anisotome pilifera	LOTUS Database	35616633
Annona cherimola	FooDB	FooDB
Annona muricata	KNApSAcK Database	22123792
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	FooDB
Antennaria dioica	LOTUS Database	35616633
Anthemis altissima	KNApSAcK Database	22123792
Anthriscus cerefolium	FooDB	FooDB
Antonia ovata	LOTUS Database	35616633
Apiaceae	-	KNApSAcK
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	FooDB
Apium graveolens var. secalinum	FooDB	FooDB
Apocynum venetum	LOTUS Database	35616633
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Arctium lappa	KNApSAcK Database	22123792
Aria edulis	LOTUS Database	35616633
Armoracia rusticana	FooDB	FooDB
Arnica montana	LOTUS Database	35616633
Arnica montana cv.ARBO	KNApSAcK Database	22123792
Artemisia absinthium	LOTUS Database	35616633
Artemisia armeniaca	LOTUS Database	35616633
Artemisia capillaris	Plant	KNApSAcK
Artemisia dracunculus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artemisia herba-alba	Plant	KNApSAcK
Artemisia iwayomogi	LOTUS Database	35616633
Artemisia jacutica	LOTUS Database	35616633
Artemisia montana	LOTUS Database	35616633
Artemisia scoparia.	KNApSAcK Database	22123792
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	FooDB
Artocarpus heterophyllus	FooDB	FooDB
Arum maculatum	LOTUS Database	35616633
Asimina triloba	Plant	KNApSAcK
Asparagus officinalis	FooDB	FooDB
Aster koraiensis	LOTUS Database	35616633
Aster salignus	KNApSAcK Database	22123792
Aster scaber	LOTUS Database	35616633
Astragalus asper	LOTUS Database	35616633
Astragalus cicer	LOTUS Database	35616633
Astragalus membranaceus	LOTUS Database	35616633
Astragalus onobrychis	LOTUS Database	35616633
Astragalus robustus	LOTUS Database	35616633
Astragalus sevangensis	LOTUS Database	35616633
Athyrium filix-femina	LOTUS Database	35616633
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	FooDB
Averrhoa carambola	FooDB	FooDB
Baccharis ochracea	LOTUS Database	35616633
Basella alba	FooDB	FooDB
Benincasa hispida	FooDB	FooDB
Berberis vulgaris	LOTUS Database	35616633
Bertholletia excelsa	FooDB	FooDB
Beta vulgaris	KNApSAcK Database	22123792
Beta vulgaris ssp. cicla	FooDB	PHENOL EXPLORER
Betonica officinalis	Plant	KNApSAcK
Betula pendula	LOTUS Database	35616633
Betula pubescens	LOTUS Database	35616633
Betula x obscura	LOTUS Database	35616633
Bidens pilosa	LOTUS Database	35616633
Blechnum orientale	KNApSAcK Database	22123792
Borago officinalis	FooDB	FooDB
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	FooDB
Brassica napus var. napus	FooDB	FooDB
Brassica oleracea	FooDB	FooDB
Brassica oleracea var. botrytis	FooDB	PHENOL EXPLORER
Brassica oleracea var. capitata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gemmifera	FooDB	FooDB
Brassica oleracea var. gongylodes	FooDB	FooDB
Brassica oleracea var. italica	FooDB	12720387
Brassica oleracea var. sabauda	FooDB	FooDB
Brassica oleracea var. viridis	FooDB	FooDB
Brassica oleracea var.capitata	KNApSAcK Database	22123792
Brassica rapa	FooDB	FooDB
Brassica rapa ssp. chinensis	FooDB	FooDB
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	PHENOL EXPLORER
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	FooDB
Brunfelsia grandiflora	LOTUS Database	35616633
Brunfelsia grandiflora D.DON	KNApSAcK Database	22123792
Byrsonima crassifolia	FooDB	FooDB
Cacalia hastata	LOTUS Database	35616633
Cajanus cajan	FooDB	FooDB
Calligonum leucocladum	KNApSAcK Database	22123792
Calluna vulgaris	LOTUS Database	35616633
Camellia crassicolumna	LOTUS Database	35616633
Camellia oleifera	LOTUS Database	35616633
Camellia sinensis	KNApSAcK Database	22123792
Campanula glomerata	LOTUS Database	35616633
Campanula persicifolia	LOTUS Database	35616633
Canarium ovatum	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	FooDB
Capparis spinosa	FooDB	FooDB
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Caragana spinosa	LOTUS Database	35616633
Carallia brachiata	LOTUS Database	35616633
Carica papaya	KNApSAcK Database	22123792
Carica papaya L.	Plant	KNApSAcK
Carissa macrocarpa	FooDB	FooDB
Carpinus laxiflora	LOTUS Database	35616633
Carthamus lanatus	LOTUS Database	35616633
Carthamus tinctorius	FooDB	FooDB
Carum carvi	FooDB	FooDB
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	FooDB
Castanea	FooDB	FooDB
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Castanopsis fissa	LOTUS Database	35616633
Cecropia hololeuca	LOTUS Database	35616633
Centaurea bracteata Scop.	Plant	KNApSAcK
Centaurea cyanus	Plant	KNApSAcK
Centaurea deflexa	LOTUS Database	35616633
Centaurea gigantea	KNApSAcK Database	22123792
Centaurea horrida	LOTUS Database	35616633
Centaurea jacea	LOTUS Database	35616633
Centaurea pseudomaculosa	LOTUS Database	35616633
Centaurea pseudoscabiosa	LOTUS Database	35616633
Centaurea pseudoscabiosa subsp.pseudoscabiosa Boiss.et aBuhse	Plant	KNApSAcK
Centella asiatica	LOTUS Database	35616633
Ceratonia siliqua	FooDB	FooDB
Chaerophyllum hirsutum	KNApSAcK Database	22123792
Chamaemelum nobile	FooDB	FooDB
Chamerion angustifolium	FooDB	FooDB
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chimarrhis turbinata	LOTUS Database	35616633
Chondrilla juncea	LOTUS Database	35616633
Chrysanthemum coccineum	LOTUS Database	35616633
Chrysanthemum coronarium	FooDB	FooDB
Chrysanthemum indicum	KNApSAcK Database	22123792
Chrysanthemum indicum L.	KNApSAcK Database	22123792
Chrysanthemum morifolium	KNApSAcK Database	22123792
Chrysanthemum vulgare	LOTUS Database	35616633
Chrysanthemum x morifolium	Plant	KNApSAcK
Cicer arietinum	FooDB	FooDB
Cichorium endivia	FooDB	FooDB
Cichorium intybus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cichorium pumilum	LOTUS Database	35616633
Cinnamomum	FooDB	FooDB
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	FooDB
Cirsium setosum	KNApSAcK Database	22123792
Citrullus colocynthis	KNApSAcK Database	22123792
Citrullus lanatus	FooDB	FooDB
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	FooDB
Citrus aurantiifolia	FooDB	FooDB
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	FooDB
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	FooDB
Citrus reticulata	FooDB	FooDB
Citrus sinensis	LOTUS Database	35616633
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	FooDB
Cocos nucifera	FooDB	FooDB
Codiaeum variegatum	LOTUS Database	35616633
Coffea arabica	KNApSAcK Database	22123792
Coffea arabica L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea canephora	FooDB	PHENOL EXPLORER
Colocasia esculenta	FooDB	FooDB
Corchorus olitorius	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cordia macleodii	KNApSAcK Database	22123792
Coriandrum sativum	LOTUS Database	35616633
Coriandrum sativum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Corylus	FooDB	FooDB
Corylus avellana	FooDB	FooDB
Cota altissima	LOTUS Database	35616633
Cotoneaster simonsii	KNApSAcK Database	22123792
Crataegus cuneata	KNApSAcK Database	22123792
Crataegus laevigata	LOTUS Database	35616633
Crataegus monogyna	LOTUS Database	35616633
Crataegus oxyacantha	KNApSAcK Database	22123792
Crataegus pinnatifida	KNApSAcK Database	22123792
Crataegus pinnatifida var.major	KNApSAcK Database	22123792
Crataegus rhipidophylla	LOTUS Database	35616633
Crataegus viridis	LOTUS Database	35616633
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	FooDB
Cryptolepis obtusa	LOTUS Database	35616633
Cucumis melo	FooDB	FooDB
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucurbita	FooDB	PHENOL EXPLORER
Cucurbita maxima	FooDB	FooDB
Cucurbita moschata	FooDB	FooDB
Cuminum cyminum	FooDB	FooDB
Curcuma longa	FooDB	FooDB
Cuscuta chinensis	LOTUS Database	35616633
Cuscuta europaea	LOTUS Database	35616633
Cuscuta reflexa	LOTUS Database	35616633
Cussonia arborea	LOTUS Database	35616633
Cyanthillium cinereum	LOTUS Database	35616633
Cyclocarya paliurus	LOTUS Database	35616633
Cydonia oblonga	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cymbopogon citratus	FooDB	FooDB
Cynanchum vincetoxicum	LOTUS Database	35616633
Cynara cardunculus	FooDB	FooDB
Cynara humilis	LOTUS Database	35616633
Cynara scolymus	FooDB	PHENOL EXPLORER
Dactylis glomerata	LOTUS Database	35616633
Daucus carota	KNApSAcK Database	22123792
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	FooDB
Dioscorea pentaphylla	FooDB	FooDB
Diospyros	FooDB	FooDB
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Dodonaea viscosa	KNApSAcK Database	22123792
Duhaldea cappa	LOTUS Database	35616633
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Echinacea angustifolia	LOTUS Database	35616633
Echinacea pallida	LOTUS Database	35616633
Echinacea paradoxa	LOTUS Database	35616633
Echinacea purpurea	LOTUS Database	35616633
Elaeagnus angustifolia	Plant	KNApSAcK
Elaeis	FooDB	FooDB
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Eleutherococcus senticosus	LOTUS Database	35616633
Eleutherococcus trichodon	LOTUS Database	35616633
Embelia schimperi	LOTUS Database	35616633
Empetrum nigrum	FooDB	FooDB
Ephedra campylopoda	LOTUS Database	35616633
Ephedra sinica	KNApSAcK Database	22123792
Epilobium roseum	LOTUS Database	35616633
Epimedium koreanum	KNApSAcK Database	22123792
Epimedium sagittatum	KNApSAcK Database	22123792
Equisetum fluviatile	LOTUS Database	35616633
Eragrostis tef	FooDB	FooDB
Eremochloa ophiuroides	LOTUS Database	35616633
Erigeron breviscapus	LOTUS Database	35616633
Erigeron canadensis	LOTUS Database	35616633
Eriobotrya japonica	KNApSAcK Database	22123792
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Erycibe schimidtii	KNApSAcK Database	22123792
Eryngium campestre	LOTUS Database	35616633
Etlingera elatior	KNApSAcK Database	22123792
Eucalyptus cypellocarpa	LOTUS Database	35616633
Eucalyptus globulus	LOTUS Database	35616633
Eucommia ulmoides	LOTUS Database	35616633
Eucommia ulmoides Oliver	KNApSAcK Database	22123792
Eugenia jambolana	KNApSAcK Database	22123792
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Euonymus alatus	LOTUS Database	35616633
Eupatorium cannabinum	LOTUS Database	35616633
Eupatorium perfoliatum	LOTUS Database	35616633
Eutrema japonicum	FooDB	FooDB
Fagopyrum cymosum	KNApSAcK Database	22123792
Fagopyrum esculentum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Falcaria vulgaris	KNApSAcK Database	22123792
Feijoa sellowiana	FooDB	FooDB
Ferula elaeochytris	Plant	KNApSAcK
Ficus carica	FooDB	FooDB
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Fontanesia philliraeoides	LOTUS Database	35616633
Forsythia europaea	LOTUS Database	35616633
Fragaria x ananassa	FooDB	PHENOL EXPLORER
Fumaria capreolata	Plant	KNApSAcK
Fumaria officinalis	Plant	KNApSAcK
Fumaria schleicheri	Plant	KNApSAcK
Fumaria vaillantii	Plant	KNApSAcK
Galium aparine	LOTUS Database	35616633
Galium verum	KNApSAcK Database	22123792
Garcinia jasminoides	KNApSAcK Database	22123792
Garcinia mangostana	FooDB	FooDB
Gardenia jasminoides	LOTUS Database	35616633
Gaylussacia baccata	FooDB	PHENOL EXPLORER
Ginkgo biloba	FooDB	FooDB
Glehnia littoralis	KNApSAcK Database	22123792
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium	FooDB	FooDB
Gossypium barbadense	KNApSAcK Database	22123792
Grifola frondosa	FooDB	FooDB
Haematoxylum campechianum	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Hedeoma drummondii	LOTUS Database	35616633
Hedera helix	LOTUS Database	35616633
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus	LOTUS Database	35616633
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helianthus annuus L.cv.Peredovick	KNApSAcK Database	22123792
Helianthus tuberosus	FooDB	FooDB
Helichrysum arenarium	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Helichrysum stoechas	LOTUS Database	35616633
Heliopsis helianthoides	LOTUS Database	35616633
Helleborus atrorubens	LOTUS Database	35616633
Hemarthria altissima	LOTUS Database	35616633
Heteropappus biennis	LOTUS Database	35616633
Hibiscus sabbariffa	FooDB	FooDB
Hieracium gymnocephalum	LOTUS Database	35616633
Hieracium naegelianum	LOTUS Database	35616633
Hintonia standleyana	LOTUS Database	35616633
Hippophae rhamnoides	KNApSAcK Database	22123792
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Houttuynia cordata	KNApSAcK Database	22123792
Humulus lupulus	KNApSAcK Database	22123792
Hydrangea macrophylla	LOTUS Database	35616633
Hydrangea macrophylla cv.Hovaria	Plant	KNApSAcK
Hydrastis canadensis	KNApSAcK Database	22123792
Hydrophyllum tenuipes	LOTUS Database	35616633
Hydrostachys polymorpha	LOTUS Database	35616633
Hypericum androsaemum	LOTUS Database	35616633
Hypericum aucheri	LOTUS Database	35616633
Hypericum calycinum	LOTUS Database	35616633
Hypericum connatum	LOTUS Database	35616633
Hypericum hirsutum	LOTUS Database	35616633
Hypericum humifusum	LOTUS Database	35616633
Hypericum japonicum	LOTUS Database	35616633
Hypericum maculatum	LOTUS Database	35616633
Hypericum montbretii	LOTUS Database	35616633
Hypericum perforatum	KNApSAcK Database	22123792
Hypericum sikokumontanum	LOTUS Database	35616633
Hypericum triquetrifolium	LOTUS Database	35616633
Hyssopus officinalis L.	FooDB	FooDB
Ilex argentina	LOTUS Database	35616633
Ilex paraguariensis	Plant	KNApSAcK
Illicium verum	FooDB	FooDB
Inula britannica	KNApSAcK Database	22123792
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ipomoea carnea	LOTUS Database	35616633
Ipomoea nil	KNApSAcK Database	22123792
Ipomoea njil cv. Danjuro	KNApSAcK Database	22123792
Isodon japonicus	LOTUS Database	35616633
Juglans	FooDB	FooDB
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	FooDB
Juglans regia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Kalopanax septemlobus	LOTUS Database	35616633
Kandelia candel	LOTUS Database	35616633
Lablab purpureus	FooDB	FooDB
Lactuca indica	KNApSAcK Database	22123792
Lactuca sativa	FooDB	15986496
Lactuca viminea	LOTUS Database	35616633
Lagenaria siceraria	FooDB	FooDB
Lamium album	LOTUS Database	35616633
Lamium moschatum	LOTUS Database	35616633
Lapsana communis L.	LOTUS Database	35616633
Laserpitium latifolium	LOTUS Database	35616633
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Lens culinaris	FooDB	FooDB
Lentinus edodes	FooDB	FooDB
Leontodon autumnalis	KNApSAcK Database	22123792
Leontopodium alpinum	LOTUS Database	35616633
Lepidaploa remotiflora	LOTUS Database	35616633
Lepidium sativum	FooDB	FooDB
Leucanthemum x superbum	LOTUS Database	35616633
Levisticum officinale	FooDB	FooDB
Ligusticum sinense	LOTUS Database	35616633
Ligustrum obtusifolium	LOTUS Database	35616633
Linaria macroura	LOTUS Database	35616633
Linum usitatissimum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Litchi chinensis	FooDB	FooDB
Lonicera bournei Hemsl.	LOTUS Database	35616633
Lonicera confusa	KNApSAcK Database	22123792
Lonicera fulvotomentosa	KNApSAcK Database	22123792
Lonicera hypoglauca	KNApSAcK Database	22123792
Lonicera implexa	KNApSAcK Database	22123792
Lonicera japonica	KNApSAcK Database	22123792
Lonicera similis	KNApSAcK Database	22123792
Loropetalum chinense	KNApSAcK Database	22123792
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	FooDB
Lycopus europaeus	LOTUS Database	35616633
Lythrum salicaria	KNApSAcK Database	22123792
Macadamia	FooDB	FooDB
Macadamia tetraphylla	FooDB	FooDB
Macfadyena unguis-cati	LOTUS Database	35616633
Magnolia denudata	KNApSAcK Database	22123792
Magnolia liliiflora	KNApSAcK Database	22123792
Mahonia repens	LOTUS Database	35616633
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	FooDB
Malus domestica	LOTUS Database	35616633
Malus pumila	FooDB	9818410
Mammea americana	FooDB	FooDB
Mandragora autumnalis	KNApSAcK Database	22123792
Mandragora officinarum	LOTUS Database	35616633
Mangifera indica	KNApSAcK Database	22123792
Manihot esculenta	FooDB	FooDB
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Marrubium velutinum	LOTUS Database	35616633
Marrubium vulgare	LOTUS Database	35616633
Marsdenia cundurango	KNApSAcK Database	22123792
Matricaria chamomilla	KNApSAcK Database	22123792
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Matteuccia struthiopteris	KNApSAcK Database	22123792
Medicago sativa	KNApSAcK Database	22123792
Melissa officinalis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	PHENOL EXPLORER
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Meum athamanticum	LOTUS Database	35616633
Mitragyna speciosa	Plant	KNApSAcK
Molineria capitulata	LOTUS Database	35616633
Momordica charantia	KNApSAcK Database	22123792
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	Plant	KNApSAcK
Moringa peregrina	Plant	KNApSAcK
Moringa stenopetala	Plant	KNApSAcK
Morus	FooDB	FooDB
Morus alba	KNApSAcK Database	22123792
Morus nigra	FooDB	FooDB
Musa acuminata	FooDB	FooDB
Musa x paradisiaca	FooDB	FooDB
Myosotis krylovii	LOTUS Database	35616633
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	FooDB
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	FooDB
Neolamarckia cadamba	LOTUS Database	35616633
Nephelium lappaceum	FooDB	FooDB
Nerium oleander	Plant	KNApSAcK
Nicotiana plumbaginifolia	LOTUS Database	35616633
Nicotiana tabacum	KNApSAcK Database	22123792
Nuphar lutea	FooDB	FooDB
Ocimum basilicum	FooDB	PHENOL EXPLORER
Ocimum tenuiflorum	LOTUS Database	35616633
Oenothera biennis	FooDB	FooDB
Oenothera speciosa	LOTUS Database	35616633
Olea europaea	FooDB	PHENOL EXPLORER
Onobrychis arenaria	LOTUS Database	35616633
Onobrychis viciifolia	LOTUS Database	35616633
Onopordum acanthium	KNApSAcK Database	22123792
Ophiorrhiza kuroiwai	LOTUS Database	35616633
Ophiorrhiza liukiuensis	KNApSAcK Database	22123792
Ophiorrhiza pumila	LOTUS Database	35616633
Opuntia	FooDB	FooDB
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	FooDB
Origanum majorana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum X majoricum	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	FooDB
Pachyrhizus erosus	FooDB	FooDB
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	FooDB
Panzerina lanata	LOTUS Database	35616633
Paraburkholderia phymatum	-	KNApSAcK
Paronychia kapela	LOTUS Database	35616633
Passiflora edulis	FooDB	FooDB
Passiflora pittieri	LOTUS Database	35616633
Pastinaca sativa	FooDB	FooDB
Pavetta indica	LOTUS Database	35616633
Pavetta owariensis	LOTUS Database	35616633
Pediomelum esculentum	FooDB	FooDB
Pelargonium incrassatum	LOTUS Database	35616633
Peltophorum africanum	KNApSAcK Database	22123792
Pentanema britannicum	Plant	KNApSAcK
Perideridia oregana	FooDB	FooDB
Persea americana	FooDB	F. W. Knapp. Some Characteristics of Eggplant and Avocado Poiyphenolases. J. Food Science. 30(6),...
Persicaria hydropiper	LOTUS Database	35616633
Petasites formosanus	LOTUS Database	35616633
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Peucedanum japonicum	LOTUS Database	35616633
Phacelia campanularia	LOTUS Database	35616633
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	PHENOL EXPLORER
Phellodendron amurense	KNApSAcK Database	22123792
Phlomis brunneogaleata	KNApSAcK Database	22123792
Phlomis lycia	LOTUS Database	35616633
Phoenix dactylifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Photinia melanocarpa	FooDB	PHENOL EXPLORER
Phyllanthus sellowianus	KNApSAcK Database	22123792
Phyllostachys edulis	FooDB	FooDB
Phyllostachys nigra	LOTUS Database	35616633
Physalis	FooDB	FooDB
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pinus	FooDB	FooDB
Pinus edulis	FooDB	FooDB
Piper nigrum L.	FooDB	FooDB
Pistacia vera	FooDB	FooDB
Pisum sativum	FooDB	FooDB
Plantago bellardi	KNApSAcK Database	22123792
Plantago cretica	KNApSAcK Database	22123792
Plantago depressa	LOTUS Database	35616633
Plantago lagopus	LOTUS Database	35616633
Plantago lanceolata	LOTUS Database	35616633
Plantago major	KNApSAcK Database	22123792
Platyphora ligata	-	KNApSAcK
Pleurotus ostreatus	FooDB	FooDB
Pluchea lanceolata	LOTUS Database	35616633
Polygonum alpinum	FooDB	FooDB
Polygonum amphibium	LOTUS Database	35616633
Polygonum aviculare	KNApSAcK Database	22123792
Polygonum bistorta	KNApSAcK Database	22123792
Polypodium vulgare	KNApSAcK Database	22123792
Polystichum braunii	LOTUS Database	35616633
Populus lasiocarpa	LOTUS Database	35616633
Portulaca oleracea	FooDB	FooDB
Posidonia oceanica	KNApSAcK Database	22123792
Potentilla erecta	LOTUS Database	35616633
Pouteria sapota	FooDB	FooDB
Primula veris	Plant	KNApSAcK
Prunus armeniaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus avium	KNApSAcK Database	22123792
Prunus avium L.	FooDB	FooDB
Prunus cerasus	KNApSAcK Database	22123792
Prunus domestica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus dulcis	FooDB	FooDB
Prunus mume	KNApSAcK Database	22123792
Prunus padus	LOTUS Database	35616633
Prunus persica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus persica var. nucipersica	FooDB	PHENOL EXPLORER
Prunus persica var. persica	FooDB	PHENOL EXPLORER
Prunus serrulata	LOTUS Database	35616633
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Psidium cattleianum	FooDB	FooDB
Psidium guajava	FooDB	FooDB
Psophocarpus tetragonolobus	FooDB	FooDB
Pteridium esculentum	LOTUS Database	35616633
Pterocaulon virgatum	KNApSAcK Database	22123792
Punica granatum	KNApSAcK Database	22123792
Pyrrosia davidii	KNApSAcK Database	22123792
Pyrrosia drakeana	KNApSAcK Database	22123792
Pyrrosia gralla	KNApSAcK Database	22123792
Pyrrosia lingua	KNApSAcK Database	22123792
Pyrrosia petiolosa	KNApSAcK Database	22123792
Pyrrosia pseudocalvata	KNApSAcK Database	22123792
Pyrrosia sheareri	KNApSAcK Database	22123792
Pyrus betulaefolia	Plant	KNApSAcK
Pyrus communis	FooDB	18778075
Pyrus kawakamii	LOTUS Database	35616633
Pyrus pyrifolia	FooDB	18778075
Quercus	FooDB	FooDB
Raphanus sativus	FooDB	FooDB
Raphanus sativus var. longipinnatus	FooDB	FooDB
Raphanus sativus var. sativus	FooDB	FooDB
Reichardia tingitana (L.) Roth	LOTUS Database	35616633
Reseda muricata	LOTUS Database	35616633
Reseda muricata C.Presl.	KNApSAcK Database	22123792
Rhaphiolepis bibas	Plant	KNApSAcK
Rhaponticum carthamoides	KNApSAcK Database	22123792
Rheum rhabarbarum	FooDB	FooDB
Rhododendron calophytum	Plant	KNApSAcK
Rhododendron catawbiense	KNApSAcK Database	22123792
Rhododendron fortunei	KNApSAcK Database	22123792
Rhododendron insigne	KNApSAcK Database	22123792
Rhododendron kaempferi	KNApSAcK Database	22123792
Rhododendron micranthum	KNApSAcK Database	22123792
Rhododendron oreotrephes	KNApSAcK Database	22123792
Rhododendron ponticum	KNApSAcK Database	22123792
Rhododendron praevernum	KNApSAcK Database	22123792
Rhododendron ungernii	Plant	KNApSAcK
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ribes rubrum	FooDB	PHENOL EXPLORER
Ribes uva-crispa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ripariosida hermaphrodita	LOTUS Database	35616633
Rosa	FooDB	FooDB
Rubia tinctorum	LOTUS Database	35616633
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	PHENOL EXPLORER
Rubus occidentalis	FooDB	PHENOL EXPLORER
Rubus spectabilis	FooDB	FooDB
Rubus ulmifolius	LOTUS Database	35616633
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	FooDB
Rumex articus	FooDB	FooDB
Sagittaria latifolia	FooDB	FooDB
Salix myrsinifolia	LOTUS Database	35616633
Salix pulchra	FooDB	FooDB
Salvia albimaculata	KNApSAcK Database	22123792
Salvia elegans	FooDB	FooDB
Salvia fruticosa	LOTUS Database	35616633
Salvia hispanica	FooDB	FooDB
Salvia horminum	KNApSAcK Database	22123792
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia officinalis L.	KNApSAcK Database	22123792
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia triloba	KNApSAcK Database	22123792
Sambucus ebulus	LOTUS Database	35616633
Sambucus formosana	KNApSAcK Database	22123792
Sambucus nigra	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sambucus nigra L.	FooDB	FooDB
Sanicula graveolens	LOTUS Database	35616633
Sarcandra glabra	Plant	KNApSAcK
Sargentodoxa cuneata	KNApSAcK Database	22123792
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Satureja subspicata	KNApSAcK Database	22123792
Saxifraga azizoon	KNApSAcK Database	22123792
Saxifraga stolonifera	LOTUS Database	35616633
Scabiosa comosa	Plant	KNApSAcK
Schinus molle	LOTUS Database	35616633
Scolymus hispanicus	LOTUS Database	35616633
Scorzonera divaricata	KNApSAcK Database	22123792
Scorzonera hispanica	FooDB	FooDB
Scorzonera humilis	LOTUS Database	35616633
Scorzoneroides autumnalis	Plant	KNApSAcK
Scrophularia cryptophila	LOTUS Database	35616633
Secale cereale	FooDB	FooDB
Secamone afzelii	LOTUS Database	35616633
Sechium edule	FooDB	FooDB
Senecio nemorensis	KNApSAcK Database	22123792
Sesamum indicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sesbania bispinosa	FooDB	FooDB
Sideritis catillaris	KNApSAcK Database	22123792
Sinapis alba	FooDB	FooDB
Sinoadina racemosa	KNApSAcK Database	22123792
Sisymbrium	FooDB	FooDB
Smallanthus sonchifolius	LOTUS Database	35616633
Solanum acaule	KNApSAcK Database	22123792
Solanum bulbocastanum	KNApSAcK Database	22123792
Solanum canasense	KNApSAcK Database	22123792
Solanum cardiophyllum	KNApSAcK Database	22123792
Solanum chacoense	KNApSAcK Database	22123792
Solanum commersonii	KNApSAcK Database	22123792
Solanum fendleri	KNApSAcK Database	22123792
Solanum habrochaites	KNApSAcK Database	22123792
Solanum hougasii	KNApSAcK Database	22123792
Solanum incanum	LOTUS Database	35616633
Solanum lycopersicum	KNApSAcK Database	22123792
Solanum lycopersicum var. cerasiforme	FooDB	PHENOL EXPLORER
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum melongena	FooDB	Adrian J. Parr, Annie Ng, and Keith W. Waldron Ester-Linked Phenolic Components of Carrot Cell Wa...
Solanum multidissectum	KNApSAcK Database	22123792
Solanum neorickii	KNApSAcK Database	22123792
Solanum nigrum	Plant	KNApSAcK
Solanum paniculatum	Plant	KNApSAcK
Solanum parviflorum	KNApSAcK Database	22123792
Solanum pennellii	KNApSAcK Database	22123792
Solanum peruvianum	LOTUS Database	35616633
Solanum phureja	KNApSAcK Database	22123792
Solanum pimpinellifollium	KNApSAcK Database	22123792
Solanum pinnacritisectum	KNApSAcK Database	22123792
Solanum quitoense	FooDB	FooDB
Solanum stoloniferum	KNApSAcK Database	22123792
Solanum tarijense	KNApSAcK Database	22123792
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum tuberosum L.	KNApSAcK Database	22123792
Solidago altissima L.	KNApSAcK Database	22123792
Solidago canadensis	KNApSAcK Database	22123792
Solidago virgaurea	LOTUS Database	35616633
Sonchus maritimus	LOTUS Database	35616633
Sophora flavescens	KNApSAcK Database	22123792
Sorbus aucuparia	FooDB	PHENOL EXPLORER
Sorbus tianschanica	LOTUS Database	35616633
Sorbus torminalis	LOTUS Database	35616633
Sorghum bicolor	FooDB	FooDB
Spathodea campanulata	LOTUS Database	35616633
Spinacia oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Spondias mombin	LOTUS Database	35616633
Stachys byzantina	LOTUS Database	35616633
Stachys palustris	LOTUS Database	35616633
Stachytapheta jamaicensis	-	KNApSAcK
Stachytarpheta jamaicensis	KNApSAcK Database	22123792
Stenostomum acreanum	LOTUS Database	35616633
Strobilanthes crispus	Plant	KNApSAcK
Strychnos colubrina	KNApSAcK Database	22123792
Strychnos lucida	KNApSAcK Database	22123792
Strychnos nux-vomica	KNApSAcK Database	22123792
Strychnos nux-vomica L.	Plant	KNApSAcK
Symphyotrichum subulatum	LOTUS Database	35616633
Symphyotrichum x salignum	LOTUS Database	35616633
Symphytum officinale	LOTUS Database	35616633
Syzygium aromaticum	FooDB	FooDB
Syzygium cumini	FooDB	KNAPSACK
Syzygium jambos	FooDB	FooDB
Tamarindus indica	FooDB	FooDB
Tanacetum balsamita	LOTUS Database	35616633
Tanacetum corymbosum	LOTUS Database	35616633
Taraxacum formosanum	KNApSAcK Database	22123792
Taraxacum mongolicum	KNApSAcK Database	22123792
Taraxacum officinale	KNApSAcK Database	22123792
Taraxacum sinicum	LOTUS Database	35616633
Tecoma stans	LOTUS Database	35616633
Tetragonia tetragonioides	FooDB	FooDB
Thea sinensis	KNApSAcK Database	22123792
Thelesperma	FooDB	FooDB
Theobroma cacao	KNApSAcK Database	22123792
Thymus capitatus	Plant	KNApSAcK
Thymus comosus	Plant	KNApSAcK
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tillandsia brachycaulos	LOTUS Database	35616633
Toona ciliata	KNApSAcK Database	22123792
Trachelospermum asiaticum	LOTUS Database	35616633
Trachelospermum asiaticum var.intermedium	KNApSAcK Database	22123792
Trachelospermum jasminoides	LOTUS Database	35616633
Tragopogon porrifolius	FooDB	FooDB
Tragopogon pratensis	LOTUS Database	35616633
Triadica sebifera	LOTUS Database	35616633
Trifolium alpestre	KNApSAcK Database	22123792
Trifolium medium	KNApSAcK Database	22123792
Trifolium pratense L.	KNApSAcK Database	22123792
Trigonella foenum-graecum	FooDB	PHENOL EXPLORER
Triticum	FooDB	FooDB
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Triticum durum	FooDB	FooDB
Triticum spelta	FooDB	FooDB
Triticum turanicum	FooDB	FooDB
Triticum turgidum	LOTUS Database	35616633
Tropaeolum majus	LOTUS Database	35616633
Turnera ulmifolia	Plant	KNApSAcK
Typha angustifolia	FooDB	FooDB
Uncaria hirsuta	LOTUS Database	35616633
Urceola rosea	LOTUS Database	35616633
Urospermum picroides	LOTUS Database	35616633
Urtica dioica	KNApSAcK Database	22123792
Urtica urens	LOTUS Database	35616633
Vaccinium	FooDB	FooDB
Vaccinium angustifolium	FooDB	PHENOL EXPLORER
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	PHENOL EXPLORER
Vaccinium arboreum	FooDB	FooDB
Vaccinium arctostaphylos	LOTUS Database	35616633
Vaccinium corymbosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium deliciosum	FooDB	PHENOL EXPLORER
Vaccinium dunalianum	LOTUS Database	35616633
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium ovalifolium	FooDB	PHENOL EXPLORER
Vaccinium ovatum	FooDB	PHENOL EXPLORER
Vaccinium oxycoccos	FooDB	PHENOL EXPLORER
Vaccinium parvifolium	FooDB	PHENOL EXPLORER
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	PHENOL EXPLORER
Vaccinium vitis-idaea	FooDB	PHENOL EXPLORER
Valeriana amurensis	LOTUS Database	35616633
Valeriana jatamansii	KNApSAcK Database	22123792
Valeriana prionophylla	KNApSAcK Database	22123792
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	FooDB
Verbena officinalis	Plant	KNApSAcK
Veronica didyma	Plant	KNApSAcK
Veronica montana	Plant	KNApSAcK
Veronica officinalis	Plant	KNApSAcK
Veronica orchidea	Plant	KNApSAcK
Veronica spuria	Plant	KNApSAcK
Veronica teucrium	Plant	KNApSAcK
Viburnum dilatatum	LOTUS Database	35616633
Viburnum edule	FooDB	FooDB
Viburnum opulus	LOTUS Database	35616633
Vicia faba	FooDB	FooDB
Vigna aconitifolia	FooDB	FooDB
Vigna angularis	FooDB	FooDB
Vigna mungo	FooDB	FooDB
Vigna radiata	FooDB	FooDB
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	FooDB
Vigna unguiculata var. sesquipedalis	FooDB	FooDB
Vinca major	LOTUS Database	35616633
Vincetoxicum scandens	LOTUS Database	35616633
Viscum album	LOTUS Database	35616633
Vitis	FooDB	FooDB
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Werneria nubigena	LOTUS Database	35616633
Withania somnifera	Plant	KNApSAcK
Xanthium strumarium	LOTUS Database	35616633
Xanthosoma sagittifolium	FooDB	FooDB
Youngia japonica	LOTUS Database	35616633
Zanthoxylum ailanthoides	KNApSAcK Database	22123792
Zea mays	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale	KNApSAcK Database	22123792
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Fatty acyl
Hydroxy acid
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha-hydroxy acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cinnamate ester (CHEBI:16112 )
tannin (CHEBI:16112 )
Caffeate derivatives (C00852 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	205 - 209 °C	Not Available
Boiling Point	664.95 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	40 mg/mL at 25 °C	Not Available
LogP	-0.356 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	3.44 g/L	ALOGPS
logP	0.17	ALOGPS
logP	-0.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	33.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003164

DrugBank ID

DB12029

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Chlorogenic_acid

METLIN ID

3498

PubChem Compound

1794427

PDB ID

Not Available

ChEBI ID

16112

Good Scents ID

rw1098431

References

General References

Kang J, Liu Y, Xie MX, Li S, Jiang M, Wang YD: Interactions of human serum albumin with chlorogenic acid and ferulic acid. Biochim Biophys Acta. 2004 Sep 24;1674(2):205-14. [PubMed:15374625 ]
Leuzzi R, Fulceri R, Marcolongo P, Banhegyi G, Zammarchi E, Stafford K, Burchell A, Benedetti A: Glucose 6-phosphate transport in fibroblast microsomes from glycogen storage disease type 1b patients: evidence for multiple glucose 6-phosphate transport systems. Biochem J. 2001 Jul 15;357(Pt 2):557-62. [PubMed:11439108 ]
Gonthier MP, Verny MA, Besson C, Remesy C, Scalbert A: Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. J Nutr. 2003 Jun;133(6):1853-9. [PubMed:12771329 ]
Lafay S, Gil-Izquierdo A, Manach C, Morand C, Besson C, Scalbert A: Chlorogenic acid is absorbed in its intact form in the stomach of rats. J Nutr. 2006 May;136(5):1192-7. [PubMed:16614403 ]
Cremin P, Kasim-Karakas S, Waterhouse AL: LC/ES-MS detection of hydroxycinnamates in human plasma and urine. J Agric Food Chem. 2001 Apr;49(4):1747-50. [PubMed:11308321 ]
Olthof MR, Hollman PC, Buijsman MN, van Amelsvoort JM, Katan MB: Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. J Nutr. 2003 Jun;133(6):1806-14. [PubMed:12771321 ]
Tokunaga T, Morshed SR, Otsuki S, Takayama F, Satoh T, Hashimoto K, Yasui T, Ogawa S, Kanegae H, Yokote Y, Akahane K, Kashimata M, Satoh K, Sakagami H: Effect of antioxidants, oxidants, metals and saliva on cytotoxicity induction by sodium fluoride. Anticancer Res. 2003 Sep-Oct;23(5A):3719-26. [PubMed:14666669 ]
Ejzemberg R, Da Silva MH, Pinto L, Mors WB: Action of chlorogenic acid on the complement system. An Acad Bras Cienc. 1999;71(2):273-7. [PubMed:10412494 ]
Lafay S, Morand C, Manach C, Besson C, Scalbert A: Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats. Br J Nutr. 2006 Jul;96(1):39-46. [PubMed:16869989 ]
Stavric B, Klassen R: Dietary effects on the uptake of benzo[a]pyrene. Food Chem Toxicol. 1994 Aug;32(8):727-34. [PubMed:8070737 ]
Higdon JV, Frei B: Coffee and health: a review of recent human research. Crit Rev Food Sci Nutr. 2006;46(2):101-23. [PubMed:16507475 ]
Bonita JS, Mandarano M, Shuta D, Vinson J: Coffee and cardiovascular disease: in vitro, cellular, animal, and human studies. Pharmacol Res. 2007 Mar;55(3):187-98. Epub 2007 Jan 26. [PubMed:17368041 ]

Showing NP-Card for Chlorogenic acid (NP0000578)

MOL for NP0000578 (Chlorogenic acid)

3D MOL for NP0000578 (Chlorogenic acid)

3D SDF for NP0000578 (Chlorogenic acid)

3D-SDF for NP0000578 (Chlorogenic acid)

PDB for NP0000578 (Chlorogenic acid)

3D PDB for NP0000578 (Chlorogenic acid)

SMILES for NP0000578 (Chlorogenic acid)

INCHI for NP0000578 (Chlorogenic acid)

Structure for NP0000578 (Chlorogenic acid)

3D Structure for NP0000578 (Chlorogenic acid)