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Showing NP-Card for 3-Hydroxyphenylpyruvic acid (NP0091539)

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Record Information
Version2.0
Created at2022-05-11 18:40:47 UTC
Updated at2022-05-11 18:40:47 UTC
NP-MRD IDNP0091539
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxyphenylpyruvic acid
Description3-Hydroxyphenylpyruvic acid, also known as 3-HPPA, 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. 3-Hydroxyphenylpyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). It is an intermediary compound in the biosynthesis of scytonemin. 4-Hydroxyphenylpyruvic acid (4-HPPA) is an intermediate in the metabolism of the amino acid phenylalanine. The aromatic side chain of phenylalanine is hydroxylated by the enzyme phenylalanine hydroxylase to form tyrosine. The conversion from tyrosine to 4-HPPA is in turn catalyzed by tyrosine aminotransferase. Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0091539 (3-Hydroxyphenylpyruvic acid)


  Mrv0541 02241201492D          

 13 13  0  0  0  0            999 V2000
   12.7206   -8.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7206   -8.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0062   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0062   -9.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2917   -8.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2917   -8.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4351   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1496   -8.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8641   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5786   -8.0761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8641   -6.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1496   -8.9011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5772   -7.6636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  2  0  0  0  0
 12  8  2  0  0  0  0
 13  5  1  0  0  0  0
M  END
Download

3D MOL for NP0091539 (3-Hydroxyphenylpyruvic acid)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
    3.8376    1.1071    0.7906 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4241    0.3289   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4166   -0.2537   -0.9103 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0076    0.0611   -0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6916   -0.7185   -1.2545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0353    0.7314    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3604    0.3772    0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0287    1.1655   -0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3375    0.9240   -1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9786   -0.1638   -0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304   -0.9655    0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9383   -2.0557    1.0696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0256   -0.6859    0.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8354   -1.1177   -0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    0.4850    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1659    1.8358    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5381    2.0171   -1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8553    1.5498   -1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9905   -0.3698   -0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8616   -2.9626    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4683   -1.2895    1.5206 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
  4  6  1  0
  6  7  1  0
  7 13  2  0
 13 11  1  0
 11 12  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  3 14  1  0
  6 15  1  0
  6 16  1  0
 13 21  1  0
 12 20  1  0
 10 19  1  0
  9 18  1  0
  8 17  1  0
M  END
Download

3D SDF for NP0091539 (3-Hydroxyphenylpyruvic acid)


  Mrv0541 02241201492D          

 13 13  0  0  0  0            999 V2000
   12.7206   -8.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7206   -8.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0062   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0062   -9.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2917   -8.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2917   -8.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4351   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1496   -8.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8641   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5786   -8.0761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8641   -6.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1496   -8.9011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5772   -7.6636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  2  0  0  0  0
 12  8  2  0  0  0  0
 13  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091539

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-1-2-6(4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)

> <INCHI_KEY>
PNYWALDMLUDDTA-UHFFFAOYSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.1574

> <EXACT_MASS>
180.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
16.708058593604505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3-hydroxyphenyl)-2-oxopropanoic acid

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
1.596648451333333

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.44344363750288

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9153375411289466

> <JCHEM_PKA_STRONGEST_BASIC>
-5.965395993221144

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
44.6925

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3-hydroxyphenyl)-2-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0091539 (3-Hydroxyphenylpyruvic acid)

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PDB for NP0091539 (3-Hydroxyphenylpyruvic acid)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      23.745 -15.075   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.745 -16.615   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.412 -14.305   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.412 -17.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.078 -15.075   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.078 -16.615   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.079 -14.305   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.413 -15.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.746 -14.305   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      29.080 -15.075   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      27.746 -12.765   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      26.413 -16.615   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      19.744 -14.305   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6   13                                                  
CONECT    6    4    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8                                                            
CONECT   13    5                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0091539 (3-Hydroxyphenylpyruvic acid)
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SMILES for NP0091539 (3-Hydroxyphenylpyruvic acid)
OC(=O)C(=O)CC1=CC(O)=CC=C1
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INCHI for NP0091539 (3-Hydroxyphenylpyruvic acid)
InChI=1S/C9H8O4/c10-7-3-1-2-6(4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
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View in JSmol
Synonyms
ValueSource
3-HydroxyphenylpyruvateGenerator
3-HPPAHMDB
HPPAHMDB
m-HydroxyphenylpyruvateHMDB
m-Hydroxyphenylpyruvic acidHMDB
3-(3-Hydroxyphenyl)-2-oxopropanoateHMDB
Chemical FormulaC9H8O4
Average Mass180.1574 Da
Monoisotopic Mass180.04226 Da
IUPAC Name3-(3-hydroxyphenyl)-2-oxopropanoic acid
Traditional Name3-(3-hydroxyphenyl)-2-oxopropanoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(=O)CC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C9H8O4/c10-7-3-1-2-6(4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
InChI KeyPNYWALDMLUDDTA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
  • Phenylpyruvate
    • 

  • 3-phenylpropanoic-acid
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Alpha-keto acid
    • 

  • Keto acid
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP1.12ALOGPS
logP1.6ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.92ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.69 m³·mol⁻¹ChemAxon
Polarizability16.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011663  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028354  
KNApSAcK IDNot Available
Chemspider ID4476924  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxyphenylpyruvic acid  
METLIN IDNot Available
PubChem Compound5318321  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available