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Showing NP-Card for phenylacrylic acid (NP0208298)

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Record Information
Version2.0
Created at2022-09-05 05:14:38 UTC
Updated at2022-09-05 05:14:38 UTC
NP-MRD IDNP0208298
Secondary Accession NumbersNone
Natural Product Identification
Common Namephenylacrylic acid
Description3-Phenylprop-2-enoic acid, also known as 3-phenylacrylic acid or tinzaparin, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. 3-Phenylprop-2-enoic acid is a weakly acidic compound (based on its pKa). It is generated by unspecified-gutmicro enzyme via a keto-hydrolysis-pattern5 reaction. 3-Phenylprop-2-enoic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-phenyl-1-(2,4,6-trihydroxy-3-methoxyphenyl)prop-2-en-1-one. phenylacrylic acid is found in Adenostoma sparsifolium, Aloe castellorum, Anadenanthera colubrina, Ananas comosus, Anastatica hierochuntica, Andryala pinnatifida, Anigozanthos preissii, Arabidopsis thaliana, Aragoa lucidula, Aristolochia elegans, Asparagus officinalis, Balanophora fungosa, Balanophora tobiracola, Balsamorhiza sagittata, Betula pendula, Bletilla striata, Brassica napus, Camellia sinensis, Cananga odorata, Capsicum annuum, Ceanothus velutinus, Bauhinia glauca, Chenopodium album, Cinnamomum aromaticum, Cinnamomum verum, Citrus sinensis, Colocasia antiquorum, Corymbia maculata, Cryptocarya amygdalina, Cucumis sativus, Engelhardia roxburghiana, Ephedra distachya, Ephedra equisetina, Euphorbia micractina, Euphorbia tithymaloides, Fragaria moschata, Gaultheria itoana, Globularia alypum, Goniothalamus amuyon, Goupia glabra, Gymnophyton isatidicarpum, Gynerium sagittatum, Harpagophytum procumbens, Harpagophytum zeyheri, Homo sapiens, Hoya imperialis, Illicium verum, Inula grandis, Isodon japonicus, Kaempferia galanga, Lagotis yunnanensis, Leucophyllum ambiguum, Liquidambar orientalis, Lychnophora ericoides, Marsypopetalum crassum, Medicago sativa, Melia azedarach, Ocotea quixos, Morella rubra, Olea europaea, Origanum vulgare, Oxalis pes-caprae, Ozothamnus diosmifolius, Parthenium argentatum, Pelargonium incrassatum, Petunia axillaris, Phellodendron chinense, Phyllanthus emblica, Pinus lambertiana, Plantago major, Pleurocybella porrigens, Plinia cauliflora, Populus deltoides, Populus trichocarpa, Portulaca oleracea, Posidonia oceanica, Sauromatum giganteum, Schisandra chinensis, Scrophularia nodosa, Sinapis alba, Sphagneticola trilobata, Streptomyces maritimus, Strobilanthes yunnanensis, Syringa persica, Taxus cuspidata, Vitis vinifera and Zingiber officinale. This keto-hydrolysis-pattern5 occurs in human gut microbiota.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0208298 (phenylacrylic acid)


  Mrv1652308201922452D          

 11 11  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    0.0000    0.0000    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
    0.0000    0.8250    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
    1.4289    2.4750    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    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
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  7  9  1  4  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
M  END
Download

3D MOL for NP0208298 (phenylacrylic acid)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    3.8591   -0.3913    0.3362 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3156    0.3675   -0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339    1.0805   -1.3622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8647    0.4669   -0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1300   -0.2190    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3237   -0.2079    0.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187   -0.9836    1.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -0.9951    1.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1166   -0.2051    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4878    0.5855   -0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0891    0.5613   -0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290    0.7126   -2.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3817    1.1315   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6385   -0.8772    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335   -1.5932    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9109   -1.6105    2.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1985   -0.2179    0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0618    1.2039   -1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6268    1.1911   -1.2392 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  6  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0208298 (phenylacrylic acid)


  Mrv1652308201922452D          

 11 11  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    0.0000    0.0000    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
    0.0000    0.8250    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
    1.4289    2.4750    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    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
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  7  9  1  4  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0208298

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)

> <INCHI_KEY>
WBYWAXJHAXSJNI-UHFFFAOYSA-N

> <FORMULA>
C9H8O2

> <MOLECULAR_WEIGHT>
148.161

> <EXACT_MASS>
148.052429498

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.428508082668504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-phenylprop-2-enoic acid

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
2.13608626

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.709231934706283

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
43.0599

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylacrylic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0208298 (phenylacrylic acid)

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PDB for NP0208298 (phenylacrylic acid)
HEADER    PROTEIN                                 20-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-AUG-19         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   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       4.001   6.930   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    4    5    6                                                  
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0208298 (phenylacrylic acid)
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SMILES for NP0208298 (phenylacrylic acid)
OC(=O)C=CC1=CC=CC=C1
Download
INCHI for NP0208298 (phenylacrylic acid)
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)
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Synonyms
ValueSource
3-Phenyl-2-propenoic acidChEBI
3-Phenylacrylic acidChEBI
3-Phenylpropenoic acidChEBI
Benzenepropenoic acidChEBI
Benzylideneacetic acidChEBI
beta-Phenylacrylic acidChEBI
PHCH=chco2hChEBI
Phenylacrylic acidChEBI
ZimtsaeureChEBI
3-Phenyl-2-propenoateGenerator
3-PhenylacrylateGenerator
3-PhenylpropenoateGenerator
BenzenepropenoateGenerator
BenzylideneacetateGenerator
b-PhenylacrylateGenerator
b-Phenylacrylic acidGenerator
beta-PhenylacrylateGenerator
Β-phenylacrylateGenerator
Β-phenylacrylic acidGenerator
PhenylacrylateGenerator
3-Phenylprop-2-enoateGenerator
CinnamateHMDB
2 Propenoic acid, 3 phenylMeSH
3-Phenyl- 2-propenoic acidMeSH
InnohepMeSH
TinzaparinMeSH
Tinzaparin sodiumMeSH
Chemical FormulaC9H8O2
Average Mass148.1610 Da
Monoisotopic Mass148.05243 Da
IUPAC Name3-phenylprop-2-enoic acid
Traditional Namephenylacrylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C=CC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)
InChI KeyWBYWAXJHAXSJNI-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
Adenostoma sparsifoliumLOTUS Database
Aloe castellorumLOTUS Database
Anadenanthera colubrinaLOTUS Database
Ananas comosusLOTUS Database
Anastatica hierochunticaLOTUS Database
Andryala pinnatifidaLOTUS Database
Anigozanthos preissiiLOTUS Database
Arabidopsis thalianaLOTUS Database
Aragoa lucidulaLOTUS Database
Aristolochia elegansLOTUS Database
Asparagus officinalisLOTUS Database
Balanophora fungosaLOTUS Database
Balanophora tobiracolaLOTUS Database
Balsamorhiza sagittataLOTUS Database
Betula pendulaLOTUS Database
Bletilla striataLOTUS Database
Brassica napusLOTUS Database
Camellia sinensisLOTUS Database
Cananga odorataLOTUS Database
Capsicum annuumLOTUS Database
Ceanothus velutinusLOTUS Database
Cheniella glaucaLOTUS Database
Chenopodium albumLOTUS Database
Cinnamomum aromaticumLOTUS Database
Cinnamomum verumLOTUS Database
Citrus sinensisLOTUS Database
Colocasia antiquorumLOTUS Database
Corymbia maculataLOTUS Database
Cryptocarya amygdalinaLOTUS Database
Cucumis sativusLOTUS Database
Engelhardia roxburghianaLOTUS Database
Ephedra distachyaLOTUS Database
Ephedra equisetinaLOTUS Database
Euphorbia micractinaLOTUS Database
Euphorbia tithymaloidesLOTUS Database
Fragaria moschataLOTUS Database
Gaultheria itoanaLOTUS Database
Globularia alypumLOTUS Database
Goniothalamus amuyonLOTUS Database
Goupia glabraLOTUS Database
Gymnophyton isatidicarpumLOTUS Database
Gynerium sagittatumLOTUS Database
Harpagophytum procumbensLOTUS Database
Harpagophytum zeyheriLOTUS Database
Homo sapiensLOTUS Database
Hoya imperialisLOTUS Database
Illicium verumLOTUS Database
Inula grandisLOTUS Database
Isodon japonicusLOTUS Database
Kaempferia galangaLOTUS Database
Lagotis yunnanensisLOTUS Database
Leucophyllum ambiguumLOTUS Database
Liquidambar orientalisLOTUS Database
Lychnophora ericoidesLOTUS Database
Marsypopetalum crassumLOTUS Database
Medicago sativaLOTUS Database
Melia azedarachLOTUS Database
Mespilodaphne quixosLOTUS Database
Morella rubraLOTUS Database
Olea europaeaLOTUS Database
Origanum vulgareLOTUS Database
Oxalis pes-capraeLOTUS Database
Ozothamnus diosmifoliusLOTUS Database
Parthenium argentatumLOTUS Database
Pelargonium incrassatumLOTUS Database
Petunia axillarisLOTUS Database
Phellodendron chinenseLOTUS Database
Phyllanthus emblicaLOTUS Database
Pinus lambertianaLOTUS Database
Plantago majorLOTUS Database
Pleurocybella porrigensLOTUS Database
Plinia caulifloraLOTUS Database
Populus deltoidesLOTUS Database
Populus trichocarpaLOTUS Database
Portulaca oleraceaLOTUS Database
Posidonia oceanicaLOTUS Database
Sauromatum giganteumLOTUS Database
Schisandra chinensisLOTUS Database
Scrophularia nodosaLOTUS Database
Sinapis albaLOTUS Database
Sphagneticola trilobataLOTUS Database
Streptomyces maritimusLOTUS Database
Strobilanthes yunnanensisLOTUS Database
Syringa persicaLOTUS Database
Taxus cuspidataLOTUS Database
Vitis viniferaLOTUS Database
Zingiber officinaleLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassCinnamic acids  
Direct ParentCinnamic acids  
Alternative Parents
Substituents
  • Cinnamic acid
    • 

  • Styrene
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP2.38ALOGPS
logP2.14ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.71ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability15.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0128078  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinnamic_acid  
METLIN IDNot Available
PubChem Compound8784  
PDB IDNot Available
ChEBI ID27386  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]