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Showing metabocard for 4-Hydroxycinnamic acid (HMDB0002035)

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enzymes (4) Show 4 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:33 UTC
Update Date2023-02-21 17:16:05 UTC
HMDB IDHMDB0002035
Secondary Accession Numbers
  • HMDB02035
Metabolite 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
Data?1676999765
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002035 (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 HMDB0002035 (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 HMDB0002035 (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>
HMDB0002035

> <DATABASE_NAME>
hmdb

> <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 HMDB0002035 (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 HMDB0002035 (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 HMDB0002035 (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 HMDB0002035 (4-Hydroxycinnamic acid)

OC(=O)\C=C\C1=CC=C(O)C=C1
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INCHI for HMDB0002035 (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 Stereo Labels
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-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
4-Coumaric acid, (e)-isomerMeSH
4-Coumaric acid, (Z)-isomerMeSH
4-Coumaric acid, disodium saltMeSH
p-Coumaryl alcoholMeSH
p-Hydroxycinnamic acidMeSH
Para-coumaric acidMeSH
trans-3-(4'-Hydroxyphenyl)-2-propenoic acidMeSH
trans-HPPAMeSH
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-HydroxyphenylacrylateHMDB
P-Hydroxyphenylacrylic acidHMDB
Para coumarateHMDB
Para coumaric acidHMDB
Para-coumarateHMDB
4-Hydroxycinnamic acidChEBI
trans-4-CoumarateGenerator, HMDB
(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-Cumaric acidHMDB
p-Hydroxy-trans-cinnamic acidHMDB
p-Hydroxyphenylacrylic acidHMDB
p-trans-Coumaric acidHMDB
trans-3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
trans-4-Coumaric acidHMDB
β-[4-Hydroxyphenyl]acrylic acidHMDB
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional Namecoumaric acid
CAS Registry Number501-98-4
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
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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular 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 (1994)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg129.27230932474
[M-H]-Not Available130.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00000432
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+133.51830932474
DeepCCS[M-H]-130.78830932474
DeepCCS[M-2H]-166.82330932474
DeepCCS[M+Na]+141.65130932474
AllCCS[M+H]+134.532859911
AllCCS[M+H-H2O]+130.132859911
AllCCS[M+NH4]+138.632859911
AllCCS[M+Na]+139.732859911
AllCCS[M-H]-132.732859911
AllCCS[M+Na-2H]-133.632859911
AllCCS[M+HCOO]-134.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.97 minutes32390414
Predicted by Siyang on May 30, 202210.4079 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.79 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1452.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid330.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid121.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid200.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid148.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid397.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid335.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)116.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid886.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid336.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1015.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid230.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid312.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate481.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA218.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water91.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxycinnamic acidOC(=O)\C=C\C1=CC=C(O)C=C13419.6Standard polar33892256
4-Hydroxycinnamic acidOC(=O)\C=C\C1=CC=C(O)C=C11660.4Standard non polar33892256
4-Hydroxycinnamic acidOC(=O)\C=C\C1=CC=C(O)C=C11811.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxycinnamic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O)C=C11900.4Semi standard non polar33892256
4-Hydroxycinnamic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O)C=C11876.5Semi standard non polar33892256
4-Hydroxycinnamic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C11947.3Semi standard non polar33892256
4-Hydroxycinnamic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O)C=C12164.4Semi standard non polar33892256
4-Hydroxycinnamic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O)C=C12161.5Semi standard non polar33892256
4-Hydroxycinnamic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12483.5Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.049 +/- 0.004 uMAdult (>18 years old)Male
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.94 +/- 0.897 uMAdult (>18 years old)Male
Normal		 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
BloodDetected and Quantified0.052 +/- 0.01 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.057 +/- 0.014 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.148 +/- 0.033 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.174 +/- 0.045 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.071 +/- 0.024 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.116 +/- 0.045 uMAdult (>18 years old)Male
Normal		 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
BloodDetected and Quantified0.6 +/- 0.253 uMAdult (>18 years old)Male
Normal		 details
FecesDetected and Quantified9.381 +/- 2.0712 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified0.323 (0.0122-1.578) nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected and Quantified9.0766 +/- 2.132 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified8.467 +/- 1.218 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified7.980 +/- 0.244 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.31-0.57 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.29-0.45 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.142 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.0160-2.940 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB04066
Phenol Explorer Compound ID500
FooDB IDFDB002593
KNApSAcK IDC00000152
Chemspider ID553148
KEGG Compound IDC00811
BioCyc IDCOUMARATE
BiGG ID36077
Wikipedia LinkP-Coumaric_acid
METLIN ID6450
PubChem Compound637542
PDB IDNot Available
ChEBI ID32374
Food Biomarker OntologyNot Available
VMH IDT4HCINNM
MarkerDB IDNot Available
Good Scents IDrw1384331
References
Synthesis ReferenceBen-Bassat, Arie; Sariaslani, Fateme Sima; Huang, Lisa L.; Patnaik, Ranjan; Lowe, David J. Fermentative preparation of para-hydroxycinnamic acid and cinnamic acid at alkaline ph. U.S. Pat. Appl. Publ. (2005), 23 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]
  3. Zhao Z, Egashira Y, Sanada H: Phenolic antioxidants richly contained in corn bran are slightly bioavailable in rats. J Agric Food Chem. 2005 Jun 15;53(12):5030-5. [PubMed:15941352 ]
  4. Brivet M, Garcia-Cazorla A, Lyonnet S, Dumez Y, Nassogne MC, Slama A, Boutron A, Touati G, Legrand A, Saudubray JM: Impaired mitochondrial pyruvate importation in a patient and a fetus at risk. Mol Genet Metab. 2003 Mar;78(3):186-92. [PubMed:12649063 ]
  5. Vargas-Tah A, Gosset G: Production of Cinnamic and p-Hydroxycinnamic Acids in Engineered Microbes. Front Bioeng Biotechnol. 2015 Aug 20;3:116. doi: 10.3389/fbioe.2015.00116. eCollection 2015. [PubMed:26347861 ]

Enzymes

Enzyme Details
1. Tyrosinase
General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
Enzyme Details
2. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Hydroxycinnamic acid → 6-{4-[(1E)-2-carboxyeth-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
4-Hydroxycinnamic acid → 3,4,5-trihydroxy-6-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylic aciddetails
Enzyme Details
3. Cytosolic beta-glucosidase
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
cis-Melilotoside + Water → 4-Hydroxycinnamic acid + D-Glucosedetails
Enzyme Details
4. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
4-Hydroxycinnamic acid → p-Coumaric acid sulfatedetails