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Showing NP-Card for 4-Hydroxycinnamic acid (NP0001246)

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Record Information
Version2.0
Created at2006-05-22 14:17:33 UTC
Updated at2024-09-17 15:45:45 UTC
NP-MRD IDNP0001246
Natural Product DOIhttps://doi.org/10.57994/0881
Secondary Accession Numbers
  • NP0003000
Natural Product Identification
Common Name4-Hydroxycinnamic acid
Description4-Hydroxycinnamic acid, also known as p-Coumaric acid, is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate. P-coumaric acid is an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acid: O-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. P-Coumaric acid is the most abundant isomer of the three in nature. P-Coumaric acid exists in two forms trans-p-coumaric acid and cis-p-coumaric acid. It is a crystalline solid that is slightly soluble in water, but very soluble in ethanol and diethyl ether. 4-Hydroxycinnamic acid 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. 4-Hydroxycinnamic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 4-Hydroxycinnamic acid is found, on average, in the highest concentration within a few different foods, such as pepper (Capsicum frutescens), pineapples, and sunflowers and in a lower concentration in spinachs, kiwis, and sweet oranges. 4-Hydroxycinnamic acid has also been detected, but not quantified in several different foods, such as wild rices, soursops, garden onions, hyssops, and avocado.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001246 (4-Hydroxycinnamic acid)


  Mrv1652309272007422D          

 12 12  0  0  0  0            999 V2000
 9998.2870 9998.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1461 9999.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8601 9999.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5761 9999.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2901 9999.5851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.576110000.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.4319 9999.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7175 9999.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0029 9999.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0029 9998.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7173 9998.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4319 9998.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  1 10  1  0  0  0  0
  7  2  1  0  0  0  0
M  END
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3D MOL for NP0001246 (4-Hydroxycinnamic acid)

HMDB0002035
     RDKit          3D
4-Hydroxycinnamic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.9951   -1.0744    0.0319 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6344    0.0506   -0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5903    0.9477   -0.7912 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009    0.3386   -0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -0.5582    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0982   -0.3388    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6438    0.8291   -0.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349    0.9806   -0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8867   -0.0099    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2745    0.1858    0.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -1.1932    0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528   -1.3511    0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5478    1.5058   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8670    1.3147   -0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7403   -1.5290    0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773    1.6674   -0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4939    1.9111   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6858    0.5791    0.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9680   -1.9901    0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4795   -2.2659    0.7819 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  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
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3D SDF for NP0001246 (4-Hydroxycinnamic acid)


  Mrv1652309272007422D          

 12 12  0  0  0  0            999 V2000
 9998.2870 9998.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1461 9999.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8601 9999.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5761 9999.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2901 9999.5851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.576110000.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.4319 9999.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7175 9999.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0029 9999.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0029 9998.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7173 9998.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4319 9998.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  1 10  1  0  0  0  0
  7  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001246

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+

> <INCHI_KEY>
NGSWKAQJJWESNS-ZZXKWVIFSA-N

> <FORMULA>
C9H8O3

> <MOLECULAR_WEIGHT>
164.158

> <EXACT_MASS>
164.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.431899091719323

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.832520938333333

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.514998441470318

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.002242567462163

> <JCHEM_PKA_STRONGEST_BASIC>
-5.954717586543567

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
45.040800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coumaric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0001246 (4-Hydroxycinnamic acid)

HMDB0002035
     RDKit          3D
4-Hydroxycinnamic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.9951   -1.0744    0.0319 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6344    0.0506   -0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5903    0.9477   -0.7912 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009    0.3386   -0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -0.5582    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0982   -0.3388    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6438    0.8291   -0.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349    0.9806   -0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8867   -0.0099    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2745    0.1858    0.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -1.1932    0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528   -1.3511    0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5478    1.5058   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8670    1.3147   -0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7403   -1.5290    0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773    1.6674   -0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4939    1.9111   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6858    0.5791    0.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9680   -1.9901    0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4795   -2.2659    0.7819 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  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
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PDB for NP0001246 (4-Hydroxycinnamic acid)

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  O   UNK     0    8663.4698663.582   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8668.8068666.663   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.1398665.892   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8671.4758666.663   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8672.8088665.892   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8671.4758668.203   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8667.4738665.892   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.1398666.662   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.8058665.892   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.8058664.352   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.1398663.582   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.4738664.352   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    3    7                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8   12    2                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    1                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0001246 (4-Hydroxycinnamic acid)

COMPND    HMDB0002035
HETATM    1  O1  UNL     1       3.995  -1.074   0.032  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.634   0.051  -0.382  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.590   0.948  -0.791  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.201   0.339  -0.401  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.336  -0.558   0.002  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.098  -0.339   0.009  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.644   0.829  -0.409  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.035   0.981  -0.378  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.887  -0.010   0.061  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.275   0.186   0.074  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.317  -1.193   0.484  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.953  -1.351   0.457  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.548   1.506  -1.631  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.867   1.315  -0.759  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.740  -1.529   0.353  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.077   1.667  -0.771  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.494   1.911  -0.710  1.00  0.00           H  
HETATM   18  H6  UNL     1      -4.686   0.579   0.923  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.968  -1.990   0.835  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.479  -2.266   0.782  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7    7   12
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10   11
CONECT   10   18
CONECT   11   12   12   19
CONECT   12   20
END
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SMILES for NP0001246 (4-Hydroxycinnamic acid)

OC(=O)\C=C\C1=CC=C(O)C=C1
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INCHI for NP0001246 (4-Hydroxycinnamic acid)

InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
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View in JSmolView NMR Assignments
Synonyms
ValueSource
(2E)-3-(4-Hydroxyphenyl)acrylic acidChEBI
(e)-3-(4-Hydroxyphenyl)-2-propenoic acidChEBI
(e)-p-Coumaric acidChEBI
(e)-p-Hydroxycinnamic acidChEBI
4'-HYDROXYCINNAMIC ACIDChEBI
Naringeninic acidChEBI
p-Coumaric acidChEBI
trans-4-Hydroxycinnamic acidChEBI
trans-p-Coumaric acidChEBI
trans-p-Coumarinic acidChEBI
trans-p-HydroxycinnamateChEBI
trans-p-Hydroxycinnamic acidChEBI
trans-4-HydroxycinnamateKegg
4-HydroxycinnamateKegg
(2E)-3-(4-Hydroxyphenyl)acrylateGenerator
(e)-3-(4-Hydroxyphenyl)-2-propenoateGenerator
(e)-p-CoumarateGenerator
(e)-p-HydroxycinnamateGenerator
4'-HYDROXYCINNAMateGenerator
NaringeninateGenerator
p-CoumarateGenerator
trans-p-CoumarateGenerator
trans-p-CoumarinateGenerator
trans-4-CoumarateHMDB
3-(4-Hydroxyphenyl)-2-propenoateHMDB
3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
3-(4-Hydroxyphenyl)acrylateHMDB
3-(4-Hydroxyphenyl)acrylic acidHMDB
4-CoumarateHMDB
4-Hydroxy cinnamateHMDB
4-Hydroxy cinnamic acidHMDB
4-HydroxyphenylpropenoateHMDB
4-Hydroxyphenylpropenoic acidHMDB
b-[4-Hydroxyphenyl]acrylateHMDB
b-[4-Hydroxyphenyl]acrylic acidHMDB
beta-[4-Hydroxyphenyl]acrylateHMDB
beta-[4-Hydroxyphenyl]acrylic acidHMDB
cis-p-CoumarateHMDB
HydroxycinnamateHMDB
Hydroxycinnamic acidHMDB
p-CumarateHMDB
p-Cumaric acidHMDB
p-HydroxycinnamateHMDB
p-Hydroxycinnamic acidHMDB
p-HydroxyphenylacrylateHMDB
p-Hydroxyphenylacrylic acidHMDB
Para coumarateHMDB
Para coumaric acidHMDB
Para-coumarateHMDB
Para-coumaric acidHMDB
4-Coumaric acid, (Z)-isomerHMDB
4-Coumaric acid, disodium saltHMDB
4-Coumaric acid, (e)-isomerHMDB
p-Coumaryl alcoholHMDB
trans-3-(4'-Hydroxyphenyl)-2-propenoic acidHMDB
trans-HPPAHMDB
(2E)-3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
(2E)-3-(4-Hydroxyphenyl)prop-2-enoic acidHMDB
(e)-3-(4-Hydroxyphenyl)acrylic acidHMDB
(e)-4-Hydroxycinnamic acidHMDB
4’-hydroxycinnamic acidHMDB
p-Hydroxy-trans-cinnamic acidHMDB
p-trans-Coumaric acidHMDB
trans-3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
trans-4-Coumaric acidHMDB
Β-[4-hydroxyphenyl]acrylic acidHMDB
4-Coumaric acidHMDB, MeSH
4-Hydroxycinnamic acidChEBI
(4-Hydroxyphenyl)acrylic acid
Coumaric acid
Chemical FormulaC9H8O3
Average Mass164.1580 Da
Monoisotopic Mass164.04734 Da
IUPAC Name(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional Namecoumaric acid
CAS Registry Number7400-08-0
SMILES
OC(=O)\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
InChI KeyNGSWKAQJJWESNS-ZZXKWVIFSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)wuhonghua2011@tjutcm.edu.cnTianjin University of Traditional Chinese MedicineHong-Hua Wu2023-09-08View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abeliophyllum distichumLOTUS Database
Abies sachalinensisLOTUS Database
Abies spectabilisLOTUS Database
Abutilon indicumPlant
Acorus calamusKNApSAcK Database
Actaea japonicaLOTUS Database
Actaea racemosaKNApSAcK Database
Actaea simplexLOTUS Database
Adenostoma fasciculatumLOTUS Database
Adenostoma sparsifoliumLOTUS Database
Aegilops neglectaLOTUS Database
Ailanthus altissimaLOTUS Database
Ailanthus integrifoliaKNApSAcK Database
Ajuga reptansLOTUS Database
Albizia julibrissinLOTUS Database
Alcea roseaLOTUS Database
Allium cepaLOTUS Database
Allium chinenseLOTUS Database
Allium sativumKNApSAcK Database
Aloe veraKNApSAcK Database
Alpinia blepharocalyxKNApSAcK Database
Althaea nudifloraKNApSAcK Database
Althaea officinalisLOTUS Database
Althaea roseaKNApSAcK Database
Amelanchier sanguineaLOTUS Database
Ananas comosusKNApSAcK Database
Anigozanthos preissiiKNApSAcK Database
Annona cherimolaLOTUS Database
Annona muricataKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaLOTUS Database
Aralia elataPlant
Aristolochia cucurbitifoliaLOTUS Database
Aristolochia kaempferiLOTUS Database
Aristolochia manshuriensisKNApSAcK Database
Artemisia annuaLOTUS Database
Artemisia capillarisLOTUS Database
Artemisia dolosaLOTUS Database
Artocarpus heterophyllusLOTUS Database
Arum maculatumLOTUS Database
Aruncus dioicusLOTUS Database
Asarum sieboldiiLOTUS Database
Aspalathus linearisLOTUS Database
Asparagus officinalisKNApSAcK Database
Asperula odorataLOTUS Database
Aster indicusLOTUS Database
Astragalus membranaceusLOTUS Database
Astragalus onobrychisLOTUS Database
Avena sativaLOTUS Database
Baccharis dracunculifoliaLOTUS Database
Balanophora abbreviata B1KNApSAcK Database
Balanophora fungosaLOTUS Database
Balanophora laxifloraLOTUS Database
Balanophora tobiracolaLOTUS Database
Baloskion tetraphyllumKNApSAcK Database
Begonia nantoensisKNApSAcK Database
Bellis perennisLOTUS Database
Beta vulgarisLOTUS Database
Beta vulgaris L. var. sacchariferaKNApSAcK Database
Betonica officinalisLOTUS Database
Betula pubescensLOTUS Database
Bidens pilosaLOTUS Database
Boronia pinnataLOTUS Database
Boschniakia rossicaLOTUS Database
Brassica napusKNApSAcK Database
Brassica oleraceaLOTUS Database
Brassica oleracea var. gongylodesKNApSAcK Database
Brettanomyces anomalusLOTUS Database
Bryophyllum pinnatumKNApSAcK Database
Bryothamnion triquetrumLOTUS Database
Buddleja globosaLOTUS Database
Bulbine frutescensLOTUS Database
Bulbophyllum vaginatumKNApSAcK Database
Cajanus cajanLOTUS Database
Calligonum leucocladumKNApSAcK Database
Calocedrus formosanaLOTUS Database
Calycanthus chinensisLOTUS Database
Camellia oleiferaLOTUS Database
Camellia reticulataLOTUS Database
Camellia sinensisLOTUS Database
Campanula rotundifoliaLOTUS Database
Cananga latifoliaKNApSAcK Database
Cannabis sativaCannabisDB
      Not Available
Capparis spinosaLOTUS Database
Capsicum annuumKNApSAcK Database
Caragana spinosaLOTUS Database
Carica papayaKNApSAcK Database
Carthamus tinctoriusLOTUS Database
Castanopsis fissaLOTUS Database
Casuarina equisetifoliaLOTUS Database
Catalpa ovataKNApSAcK Database
Centaurium erythraeaLOTUS Database
Cestrum parquiLOTUS Database
Chamaecyparis formosensisKNApSAcK Database
Chelidonium majusLOTUS Database
Chromolaena odorataLOTUS Database
Chrysanthemum borealeKNApSAcK Database
Chrysanthemum coronariumLOTUS Database
Chrysanthemum morifoliumLOTUS Database
Cicer arietinumLOTUS Database
Cinnamomum kotoenseLOTUS Database
Citrus limonKNApSAcK Database
Citrus paradisiKNApSAcK Database
Citrus sinensisLOTUS Database
Clitoria ternateaLOTUS Database
Codonopsis pilosulaLOTUS Database
Coffea canephoraLOTUS Database
Colchicum kotschyiLOTUS Database
Colubrina faralaotra subsp.trichocarpa.KNApSAcK Database
Comptonia peregrinaLOTUS Database
Corchorus olitoriusLOTUS Database
Coriandrum sativumLOTUS Database
Corymbia maculataLOTUS Database
Cotoneaster orbicularisLOTUS Database
Cowania mexicanaKNApSAcK Database
Crataegus rhipidophyllaLOTUS Database
Crocus sativusKNApSAcK Database
Cryptocarya amygdalinaLOTUS Database
Cryptomeria japonicaLOTUS Database
Cucumis sativusKNApSAcK Database
Cucurbita pepoLOTUS Database
Curcuma domesticaKNApSAcK Database
Curcuma manggaLOTUS Database
Cuscuta australisKNApSAcK Database
Cuscuta chinensisLOTUS Database
Cyamopsis tetragonolobaLOTUS Database
Cyclopia falcataLOTUS Database
Cyclopia intermediaLOTUS Database
Cynomorium songaricumLOTUS Database
Cyperus papyrusKNApSAcK Database
Cyperus rotundusLOTUS Database
Cyperus rotundus L.KNApSAcK Database
Dalbergia volubilisLOTUS Database
Daucus carotaKNApSAcK Database
Davallia mariesiiLOTUS Database
Daviesia latifoliaLOTUS Database
Delphinium venulosumLOTUS Database
Deschampsia antarcticaLOTUS Database
Dichorisandra thyrsifloraKNApSAcK Database
Dioscorea alataKNApSAcK Database
Diospyros kakiLOTUS Database
Diospyros lotusLOTUS Database
Drimia elataLOTUS Database
Duhaldea cappaLOTUS Database
Echinacea angustifoliaLOTUS Database
Elegia capensisKNApSAcK Database
Eleutherococcus senticosusLOTUS Database
Ephedra alataKNApSAcK Database
Ephedra aphyllaLOTUS Database
Ephedra equisetinaKNApSAcK Database
Epichloe typhinaLOTUS Database
Epilobium hirsutumLOTUS Database
Epimedium sagittatumKNApSAcK Database
Equisetum arvenseLOTUS Database
Equisetum ramosissimumLOTUS Database
Erigeron annuusLOTUS Database
Erigeron canadensisLOTUS Database
Eucalyptus maculataKNApSAcK Database
Euphorbia tithymaloidesLOTUS Database
Euscaphis konishiiKNApSAcK Database
Eutrema japonicumPlant
Fagopyrum esculentumLOTUS Database
Fagraea gracilipesLOTUS Database
Falcaria vulgarisKNApSAcK Database
Festuca ovinaLOTUS Database
Ficaria vernaLOTUS Database
Ficus erectaLOTUS Database
Ficus septicaLOTUS Database
Forsythia viridissimaLOTUS Database
Fragaria x ananassaLOTUS Database
Fumaria vaillantiiLOTUS Database
Galinsoga quadriradiataLOTUS Database
Gaultheria procumbensLOTUS Database
Geranium pusillumLOTUS Database
Ginkgo bilobaLOTUS Database
Gliricidia sepiumLOTUS Database
Globularia alypumLOTUS Database
Glycine maxKNApSAcK Database
Gmelina arboreaLOTUS Database
Gymnadenia conopseaLOTUS Database
Gymnadenia conopsea R.BR.KNApSAcK Database
Gynerium sagittatumKNApSAcK Database
Haematoxylum brasilettoLOTUS Database
Haplophyllum acutifoliumLOTUS Database
Haplopteris anguste-elongataLOTUS Database
Hedychium gardnerianumKNApSAcK Database
Helianthus tuberosusPlant
Helichrysum italicumLOTUS Database
Hellenia speciosaLOTUS Database
Heracleum sphondyliumLOTUS Database
Heterocoma ekmanianaLOTUS Database
Hibiscus taiwanensisKNApSAcK Database
Hippophae rhamnoidesLOTUS Database
Hordeum vulgareLOTUS Database
Humulus lupulusKNApSAcK Database
Hydrangea chinensisLOTUS Database
Hypericum japonicumLOTUS Database
Ilex paraguariensisKNApSAcK Database
Impatiens balsaminaLOTUS Database
Incarvillea delavayiLOTUS Database
Incarvillea maireiLOTUS Database
Inula britannicaKNApSAcK Database
Ipomoea nilLOTUS Database
Iris ensataLOTUS Database
Isatis tinctoriaLOTUS Database
Isodon oresbiusLOTUS Database
Juglans regiaLOTUS Database
Juncus effususLOTUS Database
Juncus inflexusKNApSAcK Database
Juniperus phoeniceaLOTUS Database
Kalanchoe pinnataLOTUS Database
Kigelia africanaLOTUS Database
Lagerstroemia speciosaLOTUS Database
Lantana trifoliaLOTUS Database
Larix laricinaLOTUS Database
Larrea divaricataKNApSAcK Database
Lavandula angustifoliaLOTUS Database
Lens culinarisLOTUS Database
Lens esculentaKNApSAcK Database
Leptolaena diospyroideaKNApSAcK Database
Leptolaena paucifloraKNApSAcK Database
Ligularia cyathicepsLOTUS Database
Ligustrum japonicumLOTUS Database
Ligustrum obtusifoliumLOTUS Database
Lilium mackliniaeLOTUS Database
Lithospermum erythrorhizonKNApSAcK Database
Lolium multiflorumLOTUS Database
Lonicera japonicaKNApSAcK Database
Lonicera microphyllaLOTUS Database
Lotus corniculatusLOTUS Database
Lotus glaberLOTUS Database
Luma chequenLOTUS Database
Lupinus angustifoliusLOTUS Database
Lupinus cosentiniiPlant
Lupinus luteusPlant
Lycopus europaeusLOTUS Database
Lygodium japonicumKNApSAcK Database
Lythrum salicariaLOTUS Database
Magnolia denudataKNApSAcK Database
Magnolia liliifloraKNApSAcK Database
Magnolia obovataLOTUS Database
maize branKNApSAcK Database
Malus domesticaLOTUS Database
Malus pumilaLOTUS Database
Malus sylvestrisLOTUS Database
Malva silvestrisKNApSAcK Database
Mangifera indicaKNApSAcK Database
Marrubium cylleneumLOTUS Database
Marrubium vulgareLOTUS Database
Matricaria chamomillaKNApSAcK Database
Matteuccia struthiopterisLOTUS Database
Matthiola incanaLOTUS Database
Medicago sativaKNApSAcK Database
Medicago truncatulaKNApSAcK Database
Melilotus messanensisKNApSAcK Database
Melissa officinalisKNApSAcK Database
Mentha piperitaeKNApSAcK Database
Menyanthes trifoliataLOTUS Database
Mimosa pudicaLOTUS Database
Momordica charantiaKNApSAcK Database
Mosla chinensisLOTUS Database
Murraya euchrestifoliaLOTUS Database
Musanga cecropioidesLOTUS Database
Myodocarpus gracilisLOTUS Database
Myristica fragransLOTUS Database
Nanodea muscosaLOTUS Database
Nardostachys jatamansiLOTUS Database
Notholirion hyacinthiumKNApSAcK Database
Nymphaea albaLOTUS Database
Nymphaea caeruleaKNApSAcK Database
Ocimum basilicumKNApSAcK Database
Ocimum sanctumKNApSAcK Database
Oenanthe javanicaLOTUS Database
Oenothera elataLOTUS Database
Olea europaeaLOTUS Database
Olearia pimeleoidesLOTUS Database
Opuntia ficus-indicaLOTUS Database
Origanum vulgareLOTUS Database
Osmanthus fortuneiLOTUS Database
Osmanthus fragransLOTUS Database
Osmanthus heterophyllusLOTUS Database
Oxalis pes-capraeLOTUS Database
Panax ginsengLOTUS Database
Panicum virgatumKNApSAcK Database
Papaver somniferumLOTUS Database
Pelargonium reniformeKNApSAcK Database
Peperomia duclouxii C. DC.Plant
Peperomia duclouxii C.DC.Plant
Peperomia heyneanaLOTUS Database
Persea americanaLOTUS Database
Pertya glabrescensLOTUS Database
Petunia axillarisLOTUS Database
Phaseolus aureusPlant
Phaseolus vulgarisLOTUS Database
Phellodendron japonicum MAXIMKNApSAcK Database
Phoenix canariensisKNApSAcK Database
Phoenix dactyliferaLOTUS Database
Phragmites australisLOTUS Database
Phyllostachys edulisKNApSAcK Database
Phyllostachys nigraLOTUS Database
Picea abiesLOTUS Database
Picea ajanensisKNApSAcK Database
Picea glaucaLOTUS Database
Picea jezoensisLOTUS Database
Picea koraiensisLOTUS Database
Picea neoveitchiiLOTUS Database
Picea obovataKNApSAcK Database
Pinus pinasterLOTUS Database
Pinus radiataKNApSAcK Database
Pinus spp.KNApSAcK Database
Pinus sylvestrisLOTUS Database
Pinus taedaLOTUS Database
Piper nigrumLOTUS Database
Piper sarmentosumLOTUS Database
Pisum sativumPlant
Plantago majorKNApSAcK Database
Plantago mediaKNApSAcK Database
Platycladus orientalisLOTUS Database
Plumeria obtusaLOTUS Database
Plumeria rubraLOTUS Database
Poa huecuLOTUS Database
Polygonum amphibiumLOTUS Database
Populus albaLOTUS Database
Populus balsamiferaLOTUS Database
Populus ciliataLOTUS Database
Populus deltoidesKNApSAcK Database
Populus euphraticaLOTUS Database
Populus laurifoliaLOTUS Database
Populus spp.KNApSAcK Database
Populus szechuanicaLOTUS Database
Populus tremuloidesLOTUS Database
Populus trichocarpaKNApSAcK Database
Populus yunnanensisLOTUS Database
Portulaca oleraceaLOTUS Database
Posidonia oceanicaLOTUS Database
Potentilla erectaLOTUS Database
Potentilla fruticosaLOTUS Database
Primula acaulisLOTUS Database
Protium heptaphyllumLOTUS Database
Prunella vulgarisLOTUS Database
Prunus aviumKNApSAcK Database
Prunus domesticaLOTUS Database
Prunus serotinaKNApSAcK Database
Pteris ensiformisLOTUS Database
Pueraria candollei var. mirificaKNApSAcK Database
Punica granatumKNApSAcK Database
Pyrus communisLOTUS Database
Quercus roburLOTUS Database
Ranunculus baudotiiKNApSAcK Database
Raphanus sativusKNApSAcK Database
Reseda muricataLOTUS Database
Rhaponticum carthamoidesKNApSAcK Database
Rhodiola crenulataLOTUS Database
Rhodiola roseaLOTUS Database
Rhodiola sachalinensisKNApSAcK Database
Rhodiola sacraLOTUS Database
Ribes nigrumLOTUS Database
Rohdea chinensisLOTUS Database
Rosa laevigataLOTUS Database
Rosmarinus officinalisKNApSAcK Database
Rubus idaeusLOTUS Database
Salix purpureaPlant
Salix x rubraLOTUS Database
Salsola collinaLOTUS Database
Salvia officinalisPlant
Salvia rosmarinusLOTUS Database
Sambucus racemosaLOTUS Database
Sarcandra glabraKNApSAcK Database
Sargentodoxa cuneataLOTUS Database
Satureja subspicataKNApSAcK Database
Scolochloa festucaceaLOTUS Database
Scolymus hispanicusLOTUS Database
Scoparia dulcisLOTUS Database
Scrophularia buergerianaKNApSAcK Database
Scrophularia frutescensLOTUS Database
Scutellaria albidaLOTUS Database
Scutellaria albida subsp.albidaPlant
Secale cerealeLOTUS Database
Secamone afzeliiLOTUS Database
Serenoa repensLOTUS Database
Silphium perfoliatumLOTUS Database
Sinapis albaLOTUS Database
Solanum dasyphyllumLOTUS Database
Solanum incanumLOTUS Database
Solanum lycopersicumLOTUS Database
Solanum melongenaLOTUS Database
Solanum tuberosumKNApSAcK Database
Solidago canadensisLOTUS Database
Sophora flavescensKNApSAcK Database
Sophora japonicaKNApSAcK Database
Sophora pachycarpaLOTUS Database
Sorghum halepenseLOTUS Database
Sparganium eurycarpumLOTUS Database
Sparganium stoloniferumKNApSAcK Database
Spathodea campanulataLOTUS Database
Spiraea formosanaKNApSAcK Database
Spiraea salicifoliaLOTUS Database
Stereospermum acuminatissimumLOTUS Database
Stereospermum zenkeriKNApSAcK Database
Strelitzia reginaeKNApSAcK Database
Streptomyces lividansLOTUS Database
Syagrus romanzoffianaLOTUS Database
Syringa oblataKNApSAcK Database
Syringa reticulataLOTUS Database
Tadehagi triquetrumLOTUS Database
Tanacetum densumLOTUS Database
Tanacetum longifoliumLOTUS Database
Taraxacum formosanumPlant
Taxus baccataKNApSAcK Database
Tetrapleura tetrapteraLOTUS Database
Thalassia testudinumKNApSAcK Database
Thalia multifloraLOTUS Database
Thalictrum atriplexLOTUS Database
Theobroma cacaoLOTUS Database
Tragopogon orientalisLOTUS Database
Trifolium alpestreKNApSAcK Database
Trifolium mediumKNApSAcK Database
Trifolium pratenseLOTUS Database
Trifolium pratense L.KNApSAcK Database
Triticum turgidumLOTUS Database
Typha domingensisLOTUS Database
Typha domingensis P.KNApSAcK Database
Typha orientalisKNApSAcK Database
Vaccinium macrocarponLOTUS Database
Vaccinium myrtillusLOTUS Database
Vaccinium oxycoccosLOTUS Database
Vaccinium vitis-idaeaLOTUS Database
Verbesina virginicaLOTUS Database
Viburnum dilatatumLOTUS Database
Viburnum furcatumLOTUS Database
Viburnum opulusLOTUS Database
Viburnum suspensumLOTUS Database
Viburnum wrightiiLOTUS Database
Viscum coloratumLOTUS Database
Visnea mocaneraLOTUS Database
Vitex agnus-castusLOTUS Database
Vitis rupestrisKNApSAcK Database
Vitis viniferaKNApSAcK Database
Vittaria anguste-elongataPlant
Werneria nubigenaLOTUS Database
Xanthorrhoea resinosaLOTUS Database
Xylocarpus granatumLOTUS Database
Zea maysKNApSAcK Database
Zostera marinaLOTUS Database
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
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Styrene
  • 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 Point211.5 °CNot Available
Boiling Point346.00 to 347.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility18300 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.79Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility1.02 g/LALOGPS
logP1.74ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m³·mol⁻¹ChemAxon
Polarizability16.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002035
DrugBank IDDB04066
Phenol Explorer Compound ID500
FoodDB IDFDB004146
KNApSAcK IDC00000152
Chemspider ID553148
KEGG Compound IDC00811
BioCyc IDCOUMARATE
BiGG ID36077
Wikipedia LinkP-Coumaric_acid
METLIN ID6450
PubChem Compound637542
PDB IDNot Available
ChEBI ID32374
Good Scents IDrw1384331
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. Phan TT, Sun L, Bay BH, Chan SY, Lee ST: Dietary compounds inhibit proliferation and contraction of keloid and hypertrophic scar-derived fibroblasts in vitro: therapeutic implication for excessive scarring. J Trauma. 2003 Jun;54(6):1212-24. [PubMed:12813346 ]
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