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Showing metabocard for m-Coumaric acid (HMDB0001713)

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enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-20 22:13:20 UTC
Update Date2023-02-21 17:15:49 UTC
HMDB IDHMDB0001713
Secondary Accession Numbers
  • HMDB0062774
  • HMDB01713
  • HMDB62774
Metabolite Identification
Common Namem-Coumaric acid
Descriptionm-Coumaric acid, also known as 3-coumarate, 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. m-Coumaric acid exists in all living organisms, ranging from bacteria to humans. m-Coumaric acid (CAS: 588-30-7) is a polyphenol metabolite from caffeic acid, formed by the gut microflora. Outside of the human body, m-Coumaric acid is found, on average, in the highest concentration within a few different foods, such as olives, corns, and beers. m-Coumaric acid has also been detected, but not quantified in several different foods, such as carrots, strawberries, grape wines, garden tomato, and bilberries. MCT-mediated absorption of phenolic compounds per se and their colonic metabolites would exert a significant impact on human health (PMID:16870009 , 15479001 , 15479001 ). m-Coumaric acid is transported by the monocarboxylic acid transporter (MCT). The amount of this compound in human biofluids is diet-dependant. m-Coumaric acid is detected after the consumption of whole grain.
Structure
Data?1676999749
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001713 (m-Coumaric acid)


  Mrv1652306131923232D          

 12 12  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -0.5025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -0.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  3 12  1  0  0  0  0
M  END
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3D MOL for HMDB0001713 (m-Coumaric acid)

HMDB0001713
     RDKit          3D
m-Coumaric acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.7702    1.2928    0.3919 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260    0.0504    0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5627   -0.8855    0.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1510   -0.4197    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728    0.4717    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375    0.1160    0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6392   -1.1961    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0102   -1.4436    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9466   -0.4411    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5392    0.8573    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4514    1.9319    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1934    1.1254    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3489   -0.8681   -0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9516   -1.4779    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4112    1.5530    0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0675   -2.0295    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3009   -2.4997    0.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0028   -0.6698   -0.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7575    2.3640   -0.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833    2.1685    0.2068 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
 10 11  1  0
 10 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
  9 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for HMDB0001713 (m-Coumaric acid)


  Mrv1652306131923232D          

 12 12  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -0.5025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -0.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  3 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001713

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+

> <INCHI_KEY>
KKSDGJDHHZEWEP-SNAWJCMRSA-N

> <FORMULA>
C9H8O3

> <MOLECULAR_WEIGHT>
164.158

> <EXACT_MASS>
164.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.37256447757347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.832520938333333

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.42942136236343

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.014955066115015

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9719429291949035

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
45.040800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
m-coumaric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0001713 (m-Coumaric acid)

HMDB0001713
     RDKit          3D
m-Coumaric acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.7702    1.2928    0.3919 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260    0.0504    0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5627   -0.8855    0.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1510   -0.4197    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728    0.4717    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375    0.1160    0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6392   -1.1961    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0102   -1.4436    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9466   -0.4411    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5392    0.8573    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4514    1.9319    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1934    1.1254    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3489   -0.8681   -0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9516   -1.4779    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4112    1.5530    0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0675   -2.0295    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3009   -2.4997    0.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0028   -0.6698   -0.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7575    2.3640   -0.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833    2.1685    0.2068 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
 10 11  1  0
 10 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
  9 18  1  0
 11 19  1  0
 12 20  1  0
M  END
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PDB for HMDB0001713 (m-Coumaric acid)

HEADER    PROTEIN                                 13-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUN-19         0                                  
HETATM    1  C   UNK     0      -3.041  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.375  -0.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.709  -0.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.709  -2.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.375  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.041  -2.478   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.374  -0.938   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.960  -0.168   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.293  -0.938   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.960   1.372   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -7.042  -0.168   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0001713 (m-Coumaric acid)

COMPND    HMDB0001713
HETATM    1  O1  UNL     1       3.770   1.293   0.392  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.526   0.050   0.344  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.563  -0.886   0.364  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.151  -0.420   0.268  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.173   0.472   0.250  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.238   0.116   0.176  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.639  -1.196   0.119  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.010  -1.444   0.049  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.947  -0.441   0.036  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.539   0.857   0.093  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.451   1.932   0.083  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.193   1.125   0.162  1.00  0.00           C  
HETATM   13  H1  UNL     1       5.349  -0.868  -0.253  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.952  -1.478   0.228  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.411   1.553   0.293  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.068  -2.029   0.126  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.301  -2.500   0.005  1.00  0.00           H  
HETATM   18  H6  UNL     1      -4.003  -0.670  -0.018  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.757   2.364  -0.784  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.883   2.168   0.207  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   18
CONECT   10   11   12   12
CONECT   11   19
CONECT   12   20
END
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SMILES for HMDB0001713 (m-Coumaric acid)

OC(=O)\C=C\C1=CC(O)=CC=C1
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INCHI for HMDB0001713 (m-Coumaric acid)

InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(2E)-3-(3-Hydroxyphenyl)-2-propenoic acidChEBI
(2E)-3-(3-Hydroxyphenyl)acrylic acidChEBI
(e)-3-(3-Hydroxyphenyl)-2-propenoic acidChEBI
m-Hydroxycinnamic acidChEBI
trans-3-HydroxycinnamateChEBI
trans-3-Hydroxycinnamic acidChEBI
(2E)-3-(3-Hydroxyphenyl)prop-2-enoateKegg
(2E)-3-(3-Hydroxyphenyl)-2-propenoateGenerator
(2E)-3-(3-Hydroxyphenyl)acrylateGenerator
(e)-3-(3-Hydroxyphenyl)-2-propenoateGenerator
3-CoumarateGenerator
m-HydroxycinnamateGenerator
(2E)-3-(3-Hydroxyphenyl)prop-2-enoic acidGenerator
m-CoumarateGenerator
3'-HydroxycinnamateHMDB
3'-Hydroxycinnamic acidHMDB
3-(3-Hydroxyphenyl)-2-propenoateHMDB
3-(3-Hydroxyphenyl)-2-propenoic acidHMDB
3-(3-Hydroxyphenyl)acrylateHMDB
3-(3-Hydroxyphenyl)acrylsaeureHMDB
3-(3-Hydroxyphenyl)prop-2-enoateHMDB
3-(3-Hydroxyphenyl)prop-2-enoic acidHMDB
3-HydroxycinnamateHMDB
3-Hydroxycinnamic acidHMDB
m-Hydroxy-cinnamateHMDB
m-Hydroxy-cinnamic acidHMDB
3-Coumaric acid, (e)-isomerMeSH, HMDB
Meta-coumaric acidMeSH, HMDB
(E)-3-(3-Hydroxyphenyl)acrylic acidHMDB
(E)-3-Hydroxycinnamic acidHMDB
trans-3-(m-Hydroxyphenyl)-2-propenoic acidHMDB
trans-m-Coumaric acidHMDB
trans-m-Hydroxycinnamic acidHMDB
trans-3-CoumarateHMDB
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid
Traditional Namem-coumaric acid
CAS Registry Number14755-02-3
SMILES
OC(=O)\C=C\C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+
InChI KeyKKSDGJDHHZEWEP-SNAWJCMRSA-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-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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point192 - 194 °CNot Available
Boiling Point373.00 to 374.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility27090 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.928 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.04 g/LALOGPS
logP1.71ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.01ChemAxon
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
Polarizability16.37 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
AllCCS[M+H]+134.28632859911
AllCCS[M-H]-131.57132859911
DeepCCS[M+H]+132.52830932474
DeepCCS[M-H]-130.03730932474
DeepCCS[M-2H]-165.730932474
DeepCCS[M+Na]+140.63230932474
AllCCS[M+H]+134.332859911
AllCCS[M+H-H2O]+129.832859911
AllCCS[M+NH4]+138.432859911
AllCCS[M+Na]+139.632859911
AllCCS[M-H]-131.632859911
AllCCS[M+Na-2H]-132.532859911
AllCCS[M+HCOO]-133.632859911

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, 2022.3.79 minutes32390414
Predicted by Siyang on May 30, 202210.4554 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.82 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1482.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid333.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid122.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid202.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid152.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid400.2 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 Acid338.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)115.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid895.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid337.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1010.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid230.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid315.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate469.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA230.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water86.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
m-Coumaric acidOC(=O)\C=C\C1=CC(O)=CC=C13291.0Standard polar33892256
m-Coumaric acidOC(=O)\C=C\C1=CC(O)=CC=C11631.2Standard non polar33892256
m-Coumaric acidOC(=O)\C=C\C1=CC(O)=CC=C11758.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
m-Coumaric acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=CC(O)=C11912.0Semi standard non polar33892256
m-Coumaric acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC(/C=C/C(=O)O)=C11856.9Semi standard non polar33892256
m-Coumaric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=CC(O[Si](C)(C)C)=C11880.6Semi standard non polar33892256
m-Coumaric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC(O)=C12164.0Semi standard non polar33892256
m-Coumaric acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC(/C=C/C(=O)O)=C12121.9Semi standard non polar33892256
m-Coumaric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12381.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - m-Coumaric acid GC-MS (2 TMS)splash10-0udl-1691000000-331053d0d0b85549ac0b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - m-Coumaric acid GC-MS (Non-derivatized)splash10-0udl-1691000000-331053d0d0b85549ac0b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - m-Coumaric acid GC-EI-TOF (Non-derivatized)splash10-0udi-1891000000-049e1d80dd47b23e8c282017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - m-Coumaric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-2900000000-91ffd4c10eaed6a176322017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - m-Coumaric acid GC-MS (2 TMS) - 70eV, Positivesplash10-00y3-6390000000-f1a30e2fb9cd1fb113412017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - m-Coumaric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-03xr-7900000000-61ee2ad0ad164a1f75502015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-03xr-0900000000-4259219e89806dfe26022012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-014i-4900000000-2157a17ec65ead35585e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-00kf-9300000000-3325dd31a734dd4659bb2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-03di-0900000000-be33d196fbb525019f072012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative-QTOFsplash10-0002-0900000000-d256885fb0f35d3d66802012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid LC-ESI-QTOF , negative-QTOFsplash10-03di-0900000000-be33d196fbb525019f072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid LC-ESI-QTOF , negative-QTOFsplash10-0002-0900000000-d256885fb0f35d3d66802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 10V, Positive-QTOFsplash10-0002-1900000000-87be0242c9f5b426f6b82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 40V, Positive-QTOFsplash10-014l-9000000000-9e4128fa078e73e71cba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 30V, Negative-QTOFsplash10-0002-0900000000-d256885fb0f35d3d66802021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 30V, Positive-QTOFsplash10-0006-9100000000-1865c168df491277a4d32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 30V, Positive-QTOFsplash10-0006-9000000000-296d14129321002679a32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 20V, Positive-QTOFsplash10-00kf-9700000000-6d29cdde66b32806de5f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 10V, Positive-QTOFsplash10-0002-0900000000-9da76da83e0462c48acf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 10V, Positive-QTOFsplash10-0002-0900000000-bf33c5b8f5901c60b3322021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 35V, Negative-QTOFsplash10-014i-2900000000-11ae76e2fe36da1dfbe62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 10V, Positive-QTOFsplash10-0002-0900000000-b6bf0b46b2fa8324cf712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 6V, Positive-QTOFsplash10-00kb-0900000000-1065251e7cf92f3435332021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Coumaric acid 50V, Positive-QTOFsplash10-004i-9000000000-0a87c81608b3fbcee7c92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Coumaric acid 10V, Positive-QTOFsplash10-014j-0900000000-b5ad37fb931b464df7d52017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Coumaric acid 20V, Positive-QTOFsplash10-014j-1900000000-c66c146ee9509bf8a4132017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Coumaric acid 40V, Positive-QTOFsplash10-0fvi-9700000000-fcc332df0fcb818fe0e02017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Coumaric acid 10V, Negative-QTOFsplash10-03di-0900000000-408ac0dd8153541887502017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Coumaric acid 20V, Negative-QTOFsplash10-03di-0900000000-146bae2da386ca2d4f1a2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Coumaric acid 40V, Negative-QTOFsplash10-014m-3900000000-235b38f342376d1c9f902017-06-28Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.008 +/- 0.002 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.007 +/- 0.002 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.012 +/- 0.006 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.051 +/- 0.017 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.046 +/- 0.012 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.014 +/- 0.006 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.022 +/- 0.009 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified0.881 +/- 0.878 uMAdult (>18 years old)Male
Normal		 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
BloodDetected and Quantified0-3.4 uMAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
FecesDetected and Quantified2.0103 +/- 0.548 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified0.201 (0.0305-1.0843) nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified2.0712 +/- 0.426 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal		 details
UrineDetected and Quantified11.192 +/- 7.46 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified0.270 +/- 0.620 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.360 +/- 0.873 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.148 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.251 +/- 0.409 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.012 +/- 0.003 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.032 +/- 0.059 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463 details
UrineDetected and Quantified0.013 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.019 +/- 0.013 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.17 +/- 0.15 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.092 +/- 0.092 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.052 +/- 0.065 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.078 +/- 0.085 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified18.808 +/- 9.712 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified6.345 +/- 5.041 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 details
Associated Disorders and Diseases
Disease References
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID463
FooDB IDFDB002590
KNApSAcK IDC00052344
Chemspider ID553147
KEGG Compound IDC12621
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkM-coumaric_acid
METLIN ID305
PubChem Compound637541
PDB IDNot Available
ChEBI ID32357
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000341
Good Scents IDrw1417071
References
Synthesis ReferenceNeish, A. C. Formation of m- and p-coumaric acids by enzymic deamination of the corresponding isomers of tyrosine. Phytochemistry (Elsevier) (1961), 1 1-24.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
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  26. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

Enzyme Details
1. 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
m-Coumaric acid → 6-{3-[(1E)-2-carboxyeth-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
m-Coumaric acid → 3,4,5-trihydroxy-6-{[(2E)-3-(3-hydroxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylic aciddetails
Enzyme Details
2. 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
m-Coumaric acid → (2E)-3-[3-(sulfooxy)phenyl]prop-2-enoic aciddetails