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Showing NP-Card for enol-phenylpyruvic acid (NP0226557)

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Record Information
Version2.0
Created at2022-09-06 05:38:22 UTC
Updated at2022-09-06 05:38:22 UTC
NP-MRD IDNP0226557
Secondary Accession NumbersNone
Natural Product Identification
Common Nameenol-phenylpyruvic acid
DescriptionEnol-phenylpyruvic acid, also known as 2-hydroxy-3-phenylacrylate or enol-a-ketohydrocinnamate, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. enol-phenylpyruvic acid is found in Daphnia pulex. Enol-phenylpyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0226557 (enol-phenylpyruvic acid)


  Mrv1533005021515542D          

 12 12  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 O   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
    0.0000    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
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  4 12  1  0  0  0  0
M  END
Download

3D MOL for NP0226557 (enol-phenylpyruvic acid)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
    3.7051    1.1350    0.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    0.1224   -0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2516   -0.6968   -0.8603 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8729   -0.1631   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4941   -1.3152   -1.0670 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9718    0.6129    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4615    0.3958    0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2944    1.5097    0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6646    1.3752    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2496    0.1435    0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566   -0.9813    0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0790   -0.8338    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0543   -1.6933   -0.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304   -2.1499   -0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3380    1.4875    0.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8665    2.5309    0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3279    2.2454   -0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3250   -0.0380    0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8425   -1.9885    0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390   -1.6984    0.3292 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0226557 (enol-phenylpyruvic acid)


  Mrv1533005021515542D          

 12 12  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 O   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
    0.0000    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
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  4 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226557

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
DEDGUGJNLNLJSR-UHFFFAOYSA-N

> <FORMULA>
C9H8O3

> <MOLECULAR_WEIGHT>
164.16

> <EXACT_MASS>
164.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.26679760766877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.6174285786666662

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.747055762699627

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.788500684045138

> <JCHEM_PKA_STRONGEST_BASIC>
-6.087588205395375

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
45.02730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
enol-phenylpyruvic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0226557 (enol-phenylpyruvic acid)

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PDB for NP0226557 (enol-phenylpyruvic acid)
HEADER    PROTEIN                                 02-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-MAY-15         0                                  
HETATM    1  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    4                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0226557 (enol-phenylpyruvic acid)
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SMILES for NP0226557 (enol-phenylpyruvic acid)
OC(=O)C(O)=CC1=CC=CC=C1
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INCHI for NP0226557 (enol-phenylpyruvic acid)
InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-6,10H,(H,11,12)
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View in JSmol
Synonyms
ValueSource
2-Hydroxy-3-phenylacrylic acidChEBI
enol-alpha-Ketohydrocinnamic acidChEBI
enol-PhenylpyruvateChEBI
2-Hydroxy-3-phenylacrylateGenerator
enol-a-KetohydrocinnamateGenerator
enol-a-Ketohydrocinnamic acidGenerator
enol-alpha-KetohydrocinnamateGenerator
enol-Α-ketohydrocinnamateGenerator
enol-Α-ketohydrocinnamic acidGenerator
Chemical FormulaC9H8O3
Average Mass164.1600 Da
Monoisotopic Mass164.04734 Da
IUPAC Name2-hydroxy-3-phenylprop-2-enoic acid
Traditional Nameenol-phenylpyruvic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(O)=CC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-6,10H,(H,11,12)
InChI KeyDEDGUGJNLNLJSR-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
Daphnia pulexLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassPhenylpyruvic acid derivatives  
Direct ParentPhenylpyruvic acid derivatives  
Alternative Parents
Substituents
  • Enol-phenylpyruvate
    • 

  • Cinnamic acid or derivatives
    • 

  • Cinnamic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Enol
    • 

  • 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
logP1.55ALOGPS
logP1.62ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.79ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.03 m³·mol⁻¹ChemAxon
Polarizability16.27 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
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 LinkNot Available
METLIN IDNot Available
PubChem Compound691  
PDB IDNot Available
ChEBI ID32815  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]