Showing NP-Card for m-Coumaric acid (NP0000467)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Show more...Show more...Show more...
Record Information
Version2.0
Created at2005-11-20 22:13:20 UTC
Updated at2024-09-03 04:19:09 UTC
NP-MRD IDNP0000467
Natural Product DOIhttps://doi.org/10.57994/1649
Secondary Accession NumbersNone
Natural Product 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000467 (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
Download

3D MOL for NP0000467 (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 NP0000467 (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>
NP0000467

> <DATABASE_NAME>
NP-MRD

> <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 NP0000467 (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

PDB for NP0000467 (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
Download

3D PDB for NP0000467 (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
Download

SMILES for NP0000467 (m-Coumaric acid)

OC(=O)\C=C\C1=CC(O)=CC=C1
Download

INCHI for NP0000467 (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+
Download
View in JSmol
Synonyms
Chemical FormulaC9H8O3
Average Mass164.1580 Da
Monoisotopic Mass164.04734 Da
IUPAC Name(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid
Traditional Namem-coumaric acid
CAS Registry Number588-30-7
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
Experimental Spectra
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK 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-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting 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
LogP1.826 (est)The Good Scents Company Information System
Predicted 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
HMDB IDHMDB0001713
DrugBank IDNot Available
Phenol Explorer Compound ID463
FoodDB IDFDB002591
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
Good Scents IDrw1417071
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. Baba S, Osakabe N, Natsume M, Yasuda A, Muto Y, Hiyoshi K, Takano H, Yoshikawa T, Terao J: Absorption, metabolism, degradation and urinary excretion of rosmarinic acid after intake of Perilla frutescens extract in humans. Eur J Nutr. 2005 Feb;44(1):1-9. Epub 2004 Feb 18. [PubMed:15309457 ]
  3. Gonthier MP, Verny MA, Besson C, Remesy C, Scalbert A: Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. J Nutr. 2003 Jun;133(6):1853-9. [PubMed:12771329 ]
  4. Gomez-Ruiz JA, Leake DS, Ames JM: In vitro antioxidant activity of coffee compounds and their metabolites. J Agric Food Chem. 2007 Aug 22;55(17):6962-9. Epub 2007 Jul 27. [PubMed:17655324 ]
  5. Mennen LI, Sapinho D, Ito H, Bertrais S, Galan P, Hercberg S, Scalbert A: Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods. Br J Nutr. 2006 Jul;96(1):191-8. [PubMed:16870009 ]
  6. Konishi Y, Kobayashi S: Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. J Agric Food Chem. 2004 Oct 20;52(21):6418-24. [PubMed:15479001 ]