Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-02-03 11:38:44 UTC
Update Date2023-02-21 17:17:32 UTC
HMDB IDHMDB0011663
Secondary Accession Numbers
  • HMDB11663
Metabolite Identification
Common Name3-Hydroxyphenylpyruvic acid
Description3-Hydroxyphenylpyruvic acid 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 has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxyphenylpyruvic acid a potential biomarker for the consumption of these foods. 3-Hydroxyphenylpyruvic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 3-Hydroxyphenylpyruvic acid.
Structure
Data?1676999852
Synonyms
ValueSource
(3-Hydroxyphenyl)pyruvic acidChEBI
3-(3-Hydroxyphenyl)pyruvic acidChEBI
m-Hydroxyphenylpyruvic acidChEBI
(3-Hydroxyphenyl)pyruvateGenerator
3-(3-Hydroxyphenyl)pyruvateGenerator
m-HydroxyphenylpyruvateGenerator
3-HydroxyphenylpyruvateGenerator
3-HPPAHMDB
HPPAHMDB
3-(3-Hydroxyphenyl)-2-oxopropanoateGenerator, HMDB
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.71631661259
DarkChem[M-H]-137.07531661259
DeepCCS[M+H]+136.47930932474
DeepCCS[M-H]-134.08330932474
DeepCCS[M-2H]-169.14630932474
DeepCCS[M+Na]+143.77430932474
AllCCS[M+H]+138.032859911
AllCCS[M+H-H2O]+133.732859911
AllCCS[M+NH4]+142.032859911
AllCCS[M+Na]+143.132859911
AllCCS[M-H]-135.132859911
AllCCS[M+Na-2H]-135.832859911
AllCCS[M+HCOO]-136.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxyphenylpyruvic acidOC(=O)C(=O)CC1=CC(O)=CC=C13108.7Standard polar33892256
3-Hydroxyphenylpyruvic acidOC(=O)C(=O)CC1=CC(O)=CC=C11318.1Standard non polar33892256
3-Hydroxyphenylpyruvic acidOC(=O)C(=O)CC1=CC(O)=CC=C11774.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxyphenylpyruvic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CC1=CC=CC(O)=C11827.2Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC(CC(=O)C(=O)O)=C11824.5Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,1TMS,isomer #3C[Si](C)(C)OC(=CC1=CC=CC(O)=C1)C(=O)O2027.4Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CC1=CC=CC(O[Si](C)(C)C)=C11843.0Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(=CC1=CC=CC(O)=C1)O[Si](C)(C)C2017.9Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,2TMS,isomer #3C[Si](C)(C)OC(=CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O2012.8Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C)=C1)O[Si](C)(C)C1971.4Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C)=C1)O[Si](C)(C)C1971.9Standard non polar33892256
3-Hydroxyphenylpyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C)=C1)O[Si](C)(C)C2010.3Standard polar33892256
3-Hydroxyphenylpyruvic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CC=CC(O)=C12074.4Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC(CC(=O)C(=O)O)=C12092.4Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC1=CC=CC(O)=C1)C(=O)O2270.5Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12308.0Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC(O)=C1)O[Si](C)(C)C(C)(C)C2475.6Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O2513.3Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)O[Si](C)(C)C(C)(C)C2695.6Semi standard non polar33892256
3-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)O[Si](C)(C)C(C)(C)C2599.8Standard non polar33892256
3-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)O[Si](C)(C)C(C)(C)C2376.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-3e796fc078a6872602522017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyphenylpyruvic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00fu-9263000000-d009962460fe24b3edca2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 10V, Positive-QTOFsplash10-08gi-0900000000-5171586bb26270378b0a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 20V, Positive-QTOFsplash10-0bti-0900000000-a3e31c3a3ec99981e3b02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 40V, Positive-QTOFsplash10-0ar0-9500000000-a09621182baf2308966d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 10V, Negative-QTOFsplash10-004i-0900000000-e3b2343ff52f84dc8c772017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 20V, Negative-QTOFsplash10-055r-0900000000-11559808da8e96b47aee2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 40V, Negative-QTOFsplash10-053u-2900000000-5ab865fb05a4a105f2022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 10V, Negative-QTOFsplash10-004i-0900000000-93c192f24a5e54d2f8a92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 20V, Negative-QTOFsplash10-053r-0900000000-45f821a4209221c590972021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 40V, Negative-QTOFsplash10-05mo-9600000000-d80adc267578ae9bcbc02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 10V, Positive-QTOFsplash10-0540-0900000000-f467cd1fa4b70f39c5d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 20V, Positive-QTOFsplash10-0a4i-3900000000-fd42a0fec8859b5c52892021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyphenylpyruvic acid 40V, Positive-QTOFsplash10-05ox-9400000000-4094ab5b8d1dd3b9c5792021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Cardiosvacular risk
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 ID167870
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available