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Showing NP-Card for o-coumaric acid (NP0186792)

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Record Information
Version2.0
Created at2022-09-04 02:45:42 UTC
Updated at2022-09-04 02:45:43 UTC
NP-MRD IDNP0186792
Secondary Accession NumbersNone
Natural Product Identification
Common Nameo-coumaric acid
DescriptionCis-2-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. Cis-2-coumarate is an extremely weak basic (essentially neutral) compound (based on its pKa). o-coumaric acid is found in Aloe africana, Amburana cearensis, Artemisia argyi, Cinnamomum aromaticum, Gaultheria procumbens, Malus domestica, Malus pumila, Mikania glomerata, Olea europaea, Phoenix dactylifera, Plinia cauliflora, Punica granatum, Triticum aestivum and Vitis vinifera. o-coumaric acid was first documented in 1993 (PMID: 24248866). A monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring (PMID: 24868863).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0186792 (o-coumaric acid)


  Mrv1652308221919412D          

 12 12  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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  7  1  0  0  0  0
  7  8  2  0  0  0  0
  1  9  1  4  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  8  3  1  0  0  0  0
 12  8  1  0  0  0  0
M  END
Download

3D MOL for NP0186792 (o-coumaric acid)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
    4.3031   -0.1631   -0.5867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0406   -0.2199   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8802   -1.0395    0.8777 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403    0.5598   -0.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8898    0.7929   -1.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109    0.4089   -0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3818    1.3429   -0.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042    1.0237    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8401   -0.1888    0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8096   -1.0879    0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5439   -0.7897    0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207   -1.7523    0.2900 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5649   -0.5928    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7089    1.1642   -1.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6882    1.5491   -1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    2.2971   -0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4089    1.7519    0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8090   -0.3729    1.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9599   -2.0468    1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2241   -2.6370    0.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  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  2  0
 11 12  1  0
 11  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
 10 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0186792 (o-coumaric acid)


  Mrv1652308221919412D          

 12 12  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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  7  1  0  0  0  0
  7  8  2  0  0  0  0
  1  9  1  4  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  8  3  1  0  0  0  0
 12  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186792

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C=CC1=CC=CC=C1O

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

> <INCHI_KEY>
PMOWTIHVNWZYFI-UHFFFAOYSA-N

> <FORMULA>
C9H8O3

> <MOLECULAR_WEIGHT>
164.16

> <EXACT_MASS>
164.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.104638224688674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.832520938333333

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.352922949759328

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.237632594192524

> <JCHEM_PKA_STRONGEST_BASIC>
-6.04288311541933

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
45.04080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxycinnamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0186792 (o-coumaric acid)

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PDB for NP0186792 (o-coumaric acid)
HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3   12                                                  
CONECT    9    1   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0186792 (o-coumaric acid)
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SMILES for NP0186792 (o-coumaric acid)
OC(=O)C=CC1=CC=CC=C1O
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INCHI for NP0186792 (o-coumaric acid)
InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)
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View in JSmol
Synonyms
ValueSource
2-HydroxycinnamateChEBI
2-Hydroxycinnamic acidChEBI
3-(2-Hydroxyphenyl)acrylic acidChEBI
3-(2-Hydroxyphenyl)acrylateGenerator
cis-2-Coumaric acidGenerator
2-CoumarateHMDB
3-(2-Hydroxyphenyl)prop-2-enoateGenerator
Chemical FormulaC9H8O3
Average Mass164.1600 Da
Monoisotopic Mass164.04734 Da
IUPAC Name3-(2-hydroxyphenyl)prop-2-enoic acid
Traditional Name2-hydroxycinnamic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C=CC1=CC=CC=C1O
InChI Identifier
InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)
InChI KeyPMOWTIHVNWZYFI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Amburana cearensisLOTUS Database
Artemisia argyiLOTUS Database
Cinnamomum aromaticumLOTUS Database
Gaultheria procumbensLOTUS Database
Malus domesticaLOTUS Database
Malus pumilaLOTUS Database
Mikania glomerataLOTUS Database
Olea europaeaLOTUS Database
Phoenix dactyliferaLOTUS Database
Plinia caulifloraLOTUS Database
Punica granatumLOTUS Database
Triticum aestivumLOTUS Database
Vitis viniferaLOTUS 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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.9ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.24ChemAxon
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
Polarizability16.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062655  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB091048  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11968  
PDB IDNot Available
ChEBI ID18176  
Good Scents IDNot Available
References
General References
  1. Ngoc TM, Nhiem NX, Khoi NM, Son DC, Hung TV, Van Kiem P: A new coumarin and cytotoxic activities of constituents from Cinnamomum cassia. Nat Prod Commun. 2014 Apr;9(4):487-8. [PubMed:24868863  ] 
  2. Aliotta G, Cafiero G, Fiorentino A, Strumia S: Inhibition of radish germination and root growth by coumarin and phenylpropanoids. J Chem Ecol. 1993 Feb;19(2):175-83. doi: 10.1007/BF00993687. [PubMed:24248866  ] 
  3. LOTUS database [Link]