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Showing NP-Card for Caffeic acid (NP0000093)

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Record Information
Version2.0
Created at2006-05-22 14:17:29 UTC
Updated at2024-09-03 04:15:59 UTC
NP-MRD IDNP0000093
Natural Product DOIhttps://doi.org/10.57994/0484
Secondary Accession NumbersNone
Natural Product Identification
Common NameCaffeic acid
DescriptionCaffeic acid, also known as caffeate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid exists in all living species, ranging from bacteria to humans. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl alcohol, all of which are significant building blocks in lignin. Outside of the human body, caffeic acid has been detected, but not quantified in fats and oils and nuts. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Caffeic acid has a variety of potential pharmacological effects in in vitro studies and in animal models, and the inhibitory effect of caffeic acid on cancer cell proliferation by an oxidative mechanism in the human HT-1080 fibrosarcoma cell line has recently been established. It occurs at high levels in black chokeberry (141 mg per 100 g) and in fairly high level in lingonberry (6 mg per 100 g).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000093 (Caffeic acid)


  Mrv1652307301920012D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411   -1.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086   -1.6157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411   -0.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
Download

3D MOL for NP0000093 (Caffeic acid)

HMDB0003501
     RDKit          3D
cis-Caffeic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
   -1.7190    1.8108    0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277    1.0116    1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012    1.5552    1.5963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573   -0.3950    0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525   -1.0672    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -0.6116   -0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2346   -1.2367   -1.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -0.9788   -1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3248   -0.0969   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6372    0.1566   -1.3161 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    0.5286    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463    1.4155    0.9299 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4782    0.2469    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291    2.0980    2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5940   -0.9837    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796   -2.1762    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3307   -1.9397   -1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9603   -1.4650   -2.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678   -0.2654   -2.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    1.6720    0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1757    0.7211    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
Download

3D SDF for NP0000093 (Caffeic acid)


  Mrv1652307301920012D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411   -1.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086   -1.6157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411   -0.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000093

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)\C=C/C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2-

> <INCHI_KEY>
QAIPRVGONGVQAS-RQOWECAXSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.1574

> <EXACT_MASS>
180.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.84830373844111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

> <JCHEM_LOGP>
1.5289556166666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.276436861456105

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.143840947271056

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283746523508147

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
47.021699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
caffeicacid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000093 (Caffeic acid)

HMDB0003501
     RDKit          3D
cis-Caffeic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
   -1.7190    1.8108    0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277    1.0116    1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012    1.5552    1.5963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573   -0.3950    0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525   -1.0672    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364   -0.6116   -0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2346   -1.2367   -1.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -0.9788   -1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3248   -0.0969   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6372    0.1566   -1.3161 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    0.5286    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463    1.4155    0.9299 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4782    0.2469    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291    2.0980    2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5940   -0.9837    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796   -2.1762    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3307   -1.9397   -1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9603   -1.4650   -2.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678   -0.2654   -2.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    1.6720    0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1757    0.7211    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
Download

PDB for NP0000093 (Caffeic acid)

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.197  -2.111   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.443  -3.016   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.197  -0.571   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2   11                                                       
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    8    9                                                  
CONECT    8    5    7   10                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
CONECT   11    4   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for NP0000093 (Caffeic acid)

COMPND    HMDB0003501
HETATM    1  O1  UNL     1      -1.719   1.811   0.797  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.628   1.012   1.001  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.801   1.555   1.596  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.657  -0.395   0.717  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.653  -1.067   0.226  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.336  -0.612  -0.116  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.235  -1.237  -1.243  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.519  -0.979  -1.618  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.325  -0.097  -0.917  1.00  0.00           C  
HETATM   10  O3  UNL     1       3.637   0.157  -1.316  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.799   0.529   0.190  1.00  0.00           C  
HETATM   12  O4  UNL     1       2.546   1.415   0.930  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.478   0.247   0.556  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.629   2.098   2.434  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.594  -0.984   0.921  1.00  0.00           H  
HETATM   16  H3  UNL     1      -1.880  -2.176   0.057  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.331  -1.940  -1.844  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.960  -1.465  -2.496  1.00  0.00           H  
HETATM   19  H6  UNL     1       4.068  -0.265  -2.105  1.00  0.00           H  
HETATM   20  H7  UNL     1       3.485   1.672   0.743  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.176   0.721   1.487  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7    7   13
CONECT    7    8   17
CONECT    8    9    9   18
CONECT    9   10   11
CONECT   10   19
CONECT   11   12   13   13
CONECT   12   20
CONECT   13   21
END
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SMILES for NP0000093 (Caffeic acid)

OC(=O)\C=C/C1=CC(O)=C(O)C=C1
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INCHI for NP0000093 (Caffeic acid)

InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2-
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View in JSmol
Synonyms
ValueSource
3,4-Dihydroxycinnamic acidChEBI
CaffeateChEBI
Caffeic acidChEBI
3,4-DihydroxycinnamateGenerator
cis-CaffeateGenerator
3,4-DihydroxybenzeneacrylateHMDB
3,4-Dihydroxybenzeneacrylic acidHMDB
Caffeic acid pureHMDB
CaffeicacidHMDB
(2Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(Z)-Caffeic acidHMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
3-(3,4-Dihydroxyphenyl)propenoic acidHMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzeneHMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzeneHMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzeneHMDB
DHCAHMDB
Isocaffeic acidHMDB
cis-3,4-Dihydroxycinnamic acidHMDB
cis-Caffeic acidHMDB
Caffeic acid, monosodium saltMeSH
Caffeic acid, (e)-isomerMeSH
Caffeic acid, (Z)-isomerMeSH
Sodium caffeateMeSH
trans-Caffeic acidMeSH
Chemical FormulaC9H8O4
Average Mass180.1574 Da
Monoisotopic Mass180.04226 Da
IUPAC Name(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Traditional Namecaffeicacid
CAS Registry Number331-39-5
SMILES
OC(=O)\C=C/C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2-
InChI KeyQAIPRVGONGVQAS-RQOWECAXSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-25View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-25View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-25View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)wuhonghua2011@tjutcm.edu.cnTianjin University of Traditional Chinese MedicineHong-Hua Wu2023-09-08View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)jtkp6n@mail.missouri.eduNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)jtkp6n@mail.missouri.eduNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies spectabilisLOTUS Database
Abutilon indicumPlant
Acanthospermum australeLOTUS Database
Achillea millefoliumPlant
Acinidia rubricaulis var.coriacea-
Actaea cimicifugaPlant
Actaea dahuricaPlant
Actaea racemosaPlant
Actaea simplexLOTUS Database
Actinidia argutaPlant
Actinidia callosa var.henryiPlant
Actinidia chinensisPlant
Actinidia chrysanthaPlant
Actinidia deliciosaPlant
Actinidia erianthaPlant
Actinidia glaucophyllaPlant
Actinidia latifoliaPlant
Actinidia polyganaPlant
Adenocaulon adhaerescensPlant
Adenocaulon himalaicumLOTUS Database
Aeschynomene americanaPlant
Ageratina adenophoraPlant
Ageratina conyzoidesPlant
Agrimonia pilosa var.japonicaPlant
Alibertia macrophyllaLOTUS Database
Allium obliquumPlant
Allium sativumPlant
Aloe castellorumLOTUS Database
Amphibolis antarcticaPlant
Amphibolis griffithiiPlant
Anchusa strigosaLOTUS Database
Andrographis paniculataPlant
Androsace septentrionalisLOTUS Database
Anemone cernuaLOTUS Database
Angelica pubescensLOTUS Database
Anigozanthos preissiiPlant
Antitoxicum scanden-
Arabidopsis thalianaPlant
Arachis glabrataPlant
Arachis hypogaeaPlant
Arbutus unedoLOTUS Database
Artemisia capillarisPlant
Artemisia cinaLOTUS Database
Artemisia minorPlant
Artemisia sieversianaLOTUS Database
Aruncus diocusPlant
Asperula odorataLOTUS Database
Aster salignusPlant
Astragalus arguricusPlant
Astragalus asperLOTUS Database
Astragalus ciceroidesPlant
Astragalus flexusPlant
Astragalus floccosifoliusPlant
Astragalus levieriPlant
Astragalus onobrychisPlant
Astragalus quisqualisPlant
Astragalus saganlugensisPlant
Balanophora japonicaPlant
Balanophora laxifloraLOTUS Database
Balanophora tobiracolaLOTUS Database
Begonia nantoensisPlant
Berberis vulgarisLOTUS Database
Bergera koenegii-
Beta vulgarisPlant
Betonica officinalisLOTUS Database
Blechnum orientalePlant
Boehmeria holosericeaPlant
Boehmeria tricuspisPlant
Brainea insignisPlant
Brassica oleracea var. gongylodesPlant
Cacalia hastataLOTUS Database
Calligonum leucocladumPlant
Callisia fragransLOTUS Database
Camchaya loloanaLOTUS Database
Campanula rotundifoliaLOTUS Database
Canna indicaLOTUS Database
Caragana spinosaLOTUS Database
Carica papaya L.Plant
Carthamus tinctoriusLOTUS Database
Centaurea bracteata Scop.Plant
Centaurea cyanusLOTUS Database
Centaurea jaceaLOTUS Database
Cephalaria giganteaLOTUS Database
Ceratostigma willmottianumPlant
Cestrum parquiLOTUS Database
Chamaecyparis formosensisLOTUS Database
Chamaemelum nobilePlant
Chamomilla rectitaPlant
Chrysanthemum coccineumLOTUS Database
Chrysanthemum morifoliumLOTUS Database
Chrysanthemum vulgareLOTUS Database
Cibotium barometzPlant
Cicer arietinumPlant
Cinchona cupreaPlant
Cinchona pubescensLOTUS Database
Citrus limonPlant
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
Clematis vitalbaLOTUS Database
Coffea arabica L.Plant
Coleus blumeiLOTUS Database
Conium maculatumPlant
Convolvulus microphyllusLOTUS Database
Cordia macleodiiPlant
Cordia sebestenaLOTUS Database
Coriandrum sativumLOTUS Database
Cotoneaster orbicularisLOTUS Database
Crataegus pinnatifidaPlant
Crinum asiaticumLOTUS Database
Crocus sativusPlant
Curcuma longaPlant
Cuscuta australisPlant
Cyclocarya paliurusLOTUS Database
Cymodocea rotundataPlant
Cymodocea serrulataPlant
Datura inoxiaPlant
Dichrocephala bicolorPlant
Digitalis purpureaPlant
Dipsacus asperPlant
Dodonaea viscosaPlant
Elaeagnus angustifoliaLOTUS Database
Elsholtzia bodinieriLOTUS Database
Elsholtzia rugulosa Hemsl.Plant
Ephedra sinicaPlant
Equisetum hiemalePlant
Equsetum arvense-
Eremochloa ophiuroidesLOTUS Database
Erica arboreaLOTUS Database
Eryngium yuccifoliumPlant
Erythrina variegataPlant
Eschenbachia bliniiPlant
Eucalyptus globulusPlant
Eucommia ulmoidesPlant
Euonymus alatusLOTUS Database
Euphorbia tithymaloidesLOTUS Database
Euphrasia strictaLOTUS Database
Evolvulus alsinoidesPlant
Falcaria vulgarisPlant
Fibraurea tinctoriaLOTUS Database
Foeniculum vulgareLOTUS Database
Forsythia intermediaPlant
Forsythia suspensaLOTUS Database
Fumaria capreolataPlant
Fumaria officinalisPlant
Fumaria schleicheriPlant
Fumaria vaillantiiPlant
Gelasia latifoliaLOTUS Database
Geranium robertianumLOTUS Database
Geum japonicumLOTUS Database
Ginkgo bilobaLOTUS Database
Glechoma hederaceaLOTUS Database
Glehnia littoralisPlant
Glycine maxPlant
Gonocaryum calleryanumLOTUS Database
Gossypium barbadensePlant
Halodule uninervisPlant
Halodule wrightiiPlant
Halophila engelmanniiPlant
Halophila hawaiianaPlant
Halophila minorPlant
Hamamelis virginianaLOTUS Database
Harpagophytum procumbensPlant
Hedeoma drummondiiLOTUS Database
Hedlundia x thuringiacaLOTUS Database
Helichrysum italicumLOTUS Database
Helichrysum stoechasLOTUS Database
Hibiscus taiwanensisPlant
Houttuynia cordataLOTUS Database
Humulus lupulusPlant
Hylotelephium populifoliumLOTUS Database
Hypericum laricifoliumPlant
Hypericum sampsoniiLOTUS Database
Ilex chinensisPlant
Ilex dumosaLOTUS Database
Ilex hainanensisLOTUS Database
Ilex paraguariensisPlant
Ilex pubescensLOTUS Database
Inonotus obliquusFungi
Ipomoea batatasLOTUS Database
Ipomoea nilPlant
Ipomoea orizabensisLOTUS Database
Isodon japonicusLOTUS Database
Kalanchoe pinnataPlant
Keiskea japonicaLOTUS Database
Kigelia africanaLOTUS Database
Lagerstroemia speciosaLOTUS Database
Lantana trifoliaLOTUS Database
Larix sibiricaLOTUS Database
Lasthenia californicaLOTUS Database
Lathyrus spp.Plant
Lavandula angustifoliaLOTUS Database
Lemna aequinoctialisLOTUS Database
Leptolaena diospyroideaPlant
Leptolaena paucifloraPlant
Lespedeza bicolorPlant
Ligularia nanchuanicaLOTUS Database
Ligularia nelumbifoliaLOTUS Database
Ligusticum chuanxiongPlant
Lithospermum erythrorhizonPlant
Lonicera bournei Hemsl.LOTUS Database
Lonicera fulvotomentosaPlant
Lonicera japonicaPlant
Lonicera similisPlant
Lotus corniculatusPlant
Lotus japonicusPlant
Lychnophora ericoidesLOTUS Database
Magnolia denudataPlant
Magnolia liliifloraPlant
Mangifera indicaPlant
Matricaria chamomillaPlant
Matteuccia struthiopterisLOTUS Database
Medicago sativaPlant
Medicago truncatulaPlant
Melilotus officinalisPlant
Melissa officinalisLOTUS Database
Mentha haplocalyxPlant
Mentha piperitaePlant
Mitragyna rotundifoliaPlant
Mitragyna speciosaPlant
Momordica charantiaPlant
Monascus pilosusLOTUS Database
Monascus pilosus BCRC38072Fungi
Morella rubraLOTUS Database
Moringa oleiferaPlant
Moringa peregrinaPlant
Moringa stenopetalaPlant
Murraya euchrestifoliaLOTUS Database
Murraya paniculataPlant
Myosotis kryloviiLOTUS Database
Nardostachys jatamansiLOTUS Database
Ocimum basilicumPlant
Ocimum tenuiflorumPlant
Oenothera speciosaLOTUS Database
Onobrychis arenariaPlant
Onopordum acanthiumPlant
Ophioceras dolichostomumLOTUS Database
Origanum acutidensPlant
Origanum dictamnusLOTUS Database
Origanum vulgarePlant
Orthosiphon stamineusPlant
Oxalis pes-capraeLOTUS Database
Panicum virgatumPlant
Panzerina lanataLOTUS Database
Papaver somniferumPlant
Paronychia kapelaLOTUS Database
Paulownia coreanaLOTUS Database
Paulownia tomentosaLOTUS Database
Pelargonium incrassatumLOTUS Database
Pelargonium reniformePlant
Pellia epiphyllaPlant
Pentanema britannicumPlant
Perilla frutescensLOTUS Database
Perilla frutescens var.acuta.Plant
Petasites formosanusLOTUS Database
Petasites japonicusLOTUS Database
Petunia axillarisLOTUS Database
Phaseolus vulgarisPlant
Phedimus kamtschaticusLOTUS Database
Phellinus igniariusFungi
Phellodendron japonicum MAXIMPlant
Phlomis tuberosaPlant
Phyllanthus sellowianusPlant
Phyllospadix scouleriPlant
Phyllospadix serrulatusPlant
Phyllospadix torreyiPlant
Pinus sibiricaPlant
Pinus spp.Plant
Pisum sativumPlant
Plantago depressaLOTUS Database
Plantago lanceolataPlant
Plantago majorPlant
Plantago mediaPlant
Platycodon grandiflorusLOTUS Database
Plectranthus barbatusLOTUS Database
Polygonum avicularePlant
Populus cathayanaLOTUS Database
Populus deltoidesPlant
Populus laurifoliaLOTUS Database
Populus nigraLOTUS Database
Populus pseudosimoniiPlant
Populus spp.Plant
Populus tremuloidesLOTUS Database
Populus trichocarpaPlant
Posidonia australisPlant
Posidonia oceanicaPlant
Potentilla erectaLOTUS Database
Protea obtusifoliaLOTUS Database
Prunus aviumPlant
Prunus domesticaLOTUS Database
Prunus serrulataLOTUS Database
Pteris multifidaPlant
Pterocaulon virgatumPlant
Pueraria PhaseoloidesPlant
Punica granatumPlant
Pyrrosia sheareriPlant
Pyrus kawakamiiLOTUS Database
Quercus ilexLOTUS Database
Ranunculus baudotiiPlant
Raphanus sativusPlant
Reseda muricataLOTUS Database
Reseda muricata C.Presl.Plant
Rhaponticum carthamoidesPlant
Rhodiola crenulataLOTUS Database
Rhodiola crenulata (HOOK.f.et Thoms.) H.OHBAPlant
Rhodiola roseaLOTUS Database
Rhodiola sachalinensisPlant
Rhodiola sacraPlant
Rhododendron ponticumLOTUS Database
Rumex thyrsiflorusPlant
Salix cheilophilaPlant
Salvia albimaculataPlant
Salvia bowleyanaPlant
Salvia calycinaPlant
Salvia chinensisPlant
Salvia horminumPlant
Salvia limbataPlant
Salvia miltiorrhizaPlant
Salvia officinalisPlant
Salvia plebeiaPlant
Salvia rosmarinusPlant
Salvia sonchifoliaPlant
Salvia trijugaLOTUS Database
Salvia trilobaPlant
Salvinia molesta D.S.Mitch.Plant
Sambucus formosanaPlant
Sanicula europaeaPlant
Sarcandra glabraPlant
Sarcolaeana multiflora-
Satureja subspicataPlant
Scrophularia buergerianaPlant
Scutellaria albidaLOTUS Database
Scutellaria albida subsp.albidaPlant
Sedum takesimense NakaiPlant
Sempervivum ruthenicumLOTUS Database
Sibiraea angustataLOTUS Database
Sideritis catillarisPlant
Silphium perfoliatumLOTUS Database
Smilax corbulariaLOTUS Database
Solanum acaulePlant
Solanum angustifoliumLOTUS Database
Solanum bulbocastanumPlant
Solanum canasensePlant
Solanum cardiophyllumPlant
Solanum cernuumLOTUS Database
Solanum chacoensePlant
Solanum commersoniiPlant
Solanum fendleriPlant
Solanum habrochaitesPlant
Solanum hougasiiPlant
Solanum incanumLOTUS Database
Solanum lycopersicumPlant
Solanum melongenaLOTUS Database
Solanum multidissectumPlant
Solanum neorickiiPlant
Solanum nigrumPlant
Solanum paniculatumPlant
Solanum parviflorumPlant
Solanum pennelliiPlant
Solanum phurejaPlant
Solanum pimpinellifolliumPlant
Solanum pinnacritisectumPlant
Solanum tarijensePlant
Solanum tuberosumPlant
Solidago altissima L.Plant
Solidago virgaurea var.leiocarpaPlant
Sophora flavescensPlant
Sorghum bicolorLOTUS Database
Spartium junceumPlant
Spinacia oleraceaLOTUS Database
Stereospermum acuminatissimumLOTUS Database
Strobilanthes crispusPlant
Struthiopteris amabilis-
Struthiopteris niponica-
Styphnolobium japonicumPlant
Symphytum officinaleLOTUS Database
Syringodium filiformePlant
Syringodium isoetifoliumPlant
Tagetes lucidaLOTUS Database
Taraxacum formosanumPlant
Taraxacum mongolicumPlant
Taraxacum officinalePlant
Taxus baccataPlant
Tephrosia candidaPlant
Tephrosia purpureaPlant
Terminalia catappaPlant
Terminalia chebulaPlant
Terminalia nigrovenulosaPlant
Tetrapleura tetrapteraPlant
Thalassia ciliatumPlant
Thalassia hemprichiiPlant
Thalassia testudinumPlant
Thalassodendron ciliatumPlant
Thymus austriacusPlant
Thymus capitatusPlant
Thymus citriodorusPlant
Thymus comosusPlant
Thymus longicaulisPlant
Thymus oblongifoliusPlant
Thymus praecoxPlant
Thymus pulegioidesPlant
Thymus serpyllumPlant
Thymus sibthorpiiPlant
Thymus vulgarisPlant
Toona ciliataPlant
Trifolium pratensePlant
Triticum aestivumPlant
Tropicoporus linteusLOTUS Database
Typha domingensisLOTUS Database
Typha domingensis P.Plant
Uncaria sinensisPlant
Urtica dioicaPlant
Vaccinium dunalianumLOTUS Database
Vaccinium myrtillusLOTUS Database
Valeriana amurensisLOTUS Database
Valeriana jatamansiiPlant
Valeriana officinalisPlant
Veronica didymaPlant
Veronica montanaPlant
Veronica officinalisPlant
Veronica orchideaPlant
Veronica spuriaPlant
Veronica teucriumPlant
Viburnum dilatatumLOTUS Database
Vicia fabaLOTUS Database
Viscum albumLOTUS Database
Viscum coloratumPlant
Vitis viniferaLOTUS Database
Woodwardia orientalisPlant
Woodwardia proliferaPlant
Xanthium strumariumPlant
Zea mays L.Plant
Ziziphora clinopodioidesLOTUS Database
Zostera capricorniPlant
Zostera marinaPlant
Zostera muelleriPlant
Zostera noltiiPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point225 °Chttps://en.wikipedia.org/wiki/Caffeic_acid
Boiling Point416.00 to 417.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility54070 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.15Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP1.53ChemAxon
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003501
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012666
KNApSAcK IDNot Available
Chemspider ID1266077
KEGG Compound IDC01481
BioCyc IDCPD-8098
BiGG IDNot Available
Wikipedia LinkCaffeic acid
METLIN ID3316
PubChem Compound1549111
PDB IDNot Available
ChEBI ID17395
Good Scents IDrw1108791
References
General References
  1. Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. [PubMed:10706426 ]
  2. Saija A, Tomaino A, Trombetta D, De Pasquale A, Uccella N, Barbuzzi T, Paolino D, Bonina F: In vitro and in vivo evaluation of caffeic and ferulic acids as topical photoprotective agents. Int J Pharm. 2000 Apr 10;199(1):39-47. [PubMed:10794925 ]
  3. 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 ]
  4. 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 ]
  5. Quiles JL, Farquharson AJ, Simpson DK, Grant I, Wahle KW: Olive oil phenolics: effects on DNA oxidation and redox enzyme mRNA in prostate cells. Br J Nutr. 2002 Sep;88(3):225-34; discussion 223-4. [PubMed:12207832 ]
  6. Uno J, Tanaka R, Branchini ML, Aoki FH, Yarita K, Sano A, Fukushima K, Mikami Y, Nishimura K, Miyaji M: Atypical Cryptococcus neoformans isolate from an HIV-infected patient in Brazil. Nihon Ishinkin Gakkai Zasshi. 2001;42(3):127-32. [PubMed:11479533 ]
  7. Verma RP: A classical QSAR study on some platelet aggregation inhibitors. Mini Rev Med Chem. 2006 Apr;6(4):467-82. [PubMed:16613584 ]
  8. Li X, Yu C, Cai Y, Liu G, Jia J, Wang Y: Simultaneous determination of six phenolic constituents of danshen in human serum using liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 5;820(1):41-7. Epub 2005 Apr 19. [PubMed:15866491 ]
  9. Olthof MR, Hollman PC, Katan MB: Chlorogenic acid and caffeic acid are absorbed in humans. J Nutr. 2001 Jan;131(1):66-71. [PubMed:11208940 ]
  10. Mennen LI, Sapinho D, Ito H, Bertrais S, Galan P, Hercberg S, Scalbert A: Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods. Br J Nutr. 2006 Jul;96(1):191-8. [PubMed:16870009 ]