Showing metabocard for 4-Hydroxycinnamic acid (MMDBc0000581)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:50:25 UTC
Update Date2024-10-09 21:50:59 UTC
Metabolite IDMMDBc0000581
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000559cffd18480>


  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
Download

3D MOL for #<Metabolite:0x0000559cffd18480>

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
Download

3D SDF for #<Metabolite:0x0000559cffd18480>


  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>
MMDBc0000581

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x0000559cffd18480>

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
Download

PDB for #<Metabolite:0x0000559cffd18480>

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 #<Metabolite:0x0000559cffd18480>

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 #<Metabolite:0x0000559cffd18480>

OC(=O)\C=C\C1=CC=C(O)C=C1
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INCHI for #<Metabolite:0x0000559cffd18480>

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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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
Molecular FormulaC9H8O3
Average Mass164.158
Monoisotopic Mass164.047344122
IUPAC Name(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional Namecoumaric acid
CAS Registry NumberNot Available
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