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Showing Compound 4-hydroxyphenylpyruvate (FDB030506)

Record Information
Version1.0
Creation date2015-05-07 19:24:04 UTC
Update date2024-11-29 22:27:56 UTC
Primary IDFDB030506
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-hydroxyphenylpyruvate
Description4-Hydroxyphenylpyruvic acid, also known as 4-hydroxy a-oxobenzenepropanoate or (p-hydroxyphenyl)pyruvate, 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. 4-Hydroxyphenylpyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxyphenylpyruvic acid exists in all living species, ranging from bacteria to humans. Within humans, 4-hydroxyphenylpyruvic acid participates in a number of enzymatic reactions. In particular, 4-hydroxyphenylpyruvic acid and L-glutamic acid can be biosynthesized from L-tyrosine and oxoglutaric acid; which is catalyzed by the enzyme tyrosine aminotransferase. In addition, 4-hydroxyphenylpyruvic acid can be converted into homogentisic acid through its interaction with the enzyme 4-hydroxyphenylpyruvate dioxygenase. An oxo carboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. In humans, 4-hydroxyphenylpyruvic acid is involved in the metabolic disorder called tyrosinemia, transient, of the newborn. Outside of the human body, 4-Hydroxyphenylpyruvic acid has been detected, but not quantified in, several different foods, such as black chokeberries, limes, hazelnuts, pepper (c. baccatum), and dandelions. This could make 4-hydroxyphenylpyruvic acid a potential biomarker for the consumption of these foods. 4-Hydroxyphenylpyruvic acid is a potentially toxic compound. 4-Hydroxyphenylpyruvic acid, with regard to humans, has been found to be associated with several diseases such as deafness, onychodystrophy, osteodystrophy, mental retardation, and seizures syndrome, attachment loss, colorectal cancer, and periodontal probing depth; 4-hydroxyphenylpyruvic acid has also been linked to the inborn metabolic disorder phenylketonuria.
CAS Number156-39-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.49 g/LALOGPS
logP1.12ALOGPS
logP1.6ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
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
Polarizability16.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O4
IUPAC name3-(4-hydroxyphenyl)-2-oxopropanoic acid
InChI IdentifierInChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
InChI KeyKKADPXVIOXHVKN-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C(=O)CC1=CC=C(O)C=C1
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
Classification
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-2-unsubstituted benzenoid
  • Phenol
  • Alpha-keto acid
  • Keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a59-5900000000-6c003e26816579df31ca2014-09-20View Spectrum
GC-MS4-hydroxyphenylpyruvate, non-derivatized, GC-MS Spectrumsplash10-002f-1920000000-75b07d9c09371340939fSpectrum
GC-MS4-hydroxyphenylpyruvate, 3 TMS, GC-MS Spectrumsplash10-00xr-9340000000-087aad2497b3493d27c0Spectrum
GC-MS4-hydroxyphenylpyruvate, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-002o-5910000000-fd1e55c84c79bfeca559Spectrum
GC-MS4-hydroxyphenylpyruvate, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-002f-1941000000-2b4c87544657895fcaf6Spectrum
GC-MS4-hydroxyphenylpyruvate, 1 MEOX; 3 TMS, GC-MS Spectrumsplash10-014i-3492100000-483bdcea11d60fe4d306Spectrum
GC-MS4-hydroxyphenylpyruvate, 1 MEOX; 3 TMS, GC-MS Spectrumsplash10-014i-6791000000-ddc0a3b695cd1d0769f2Spectrum
GC-MS4-hydroxyphenylpyruvate, non-derivatized, GC-MS Spectrumsplash10-002f-1951000000-ecd071a64b26ca77684cSpectrum
GC-MS4-hydroxyphenylpyruvate, non-derivatized, GC-MS Spectrumsplash10-002f-1920000000-75b07d9c09371340939fSpectrum
GC-MS4-hydroxyphenylpyruvate, non-derivatized, GC-MS Spectrumsplash10-00xr-9340000000-087aad2497b3493d27c0Spectrum
GC-MS4-hydroxyphenylpyruvate, non-derivatized, GC-MS Spectrumsplash10-002o-5910000000-fd1e55c84c79bfeca559Spectrum
GC-MS4-hydroxyphenylpyruvate, non-derivatized, GC-MS Spectrumsplash10-002f-1941000000-2b4c87544657895fcaf6Spectrum
GC-MS4-hydroxyphenylpyruvate, non-derivatized, GC-MS Spectrumsplash10-014i-3492100000-483bdcea11d60fe4d306Spectrum
GC-MS4-hydroxyphenylpyruvate, non-derivatized, GC-MS Spectrumsplash10-014i-6791000000-ddc0a3b695cd1d0769f2Spectrum
GC-MS4-hydroxyphenylpyruvate, non-derivatized, GC-MS Spectrumsplash10-0006-2920000000-469469dfaad745fa78e8Spectrum
GC-MS4-hydroxyphenylpyruvate, non-derivatized, GC-MS Spectrumsplash10-002o-2910000000-4f336335a2366e7dd6dbSpectrum
Predicted GC-MS4-hydroxyphenylpyruvate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-6900000000-91bfe3ee54a36877251bSpectrum
Predicted GC-MS4-hydroxyphenylpyruvate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0adi-6961000000-670161f1542fda9ff1feSpectrum
Predicted GC-MS4-hydroxyphenylpyruvate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-hydroxyphenylpyruvate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-hydroxyphenylpyruvate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-hydroxyphenylpyruvate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-hydroxyphenylpyruvate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-hydroxyphenylpyruvate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-hydroxyphenylpyruvate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-hydroxyphenylpyruvate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0900000000-12033042c41b550bed422012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-0900000000-6e8a3701c6d254cc824d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0560-1900000000-8082c68e259d24234d052012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-2416d7f64101b9473cbb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-2900000000-b4c21b3d9751b9e56d672012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0005-9400000000-708e258e692a0abfbc922012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9100000000-7d75e23ae6944c1e9c6d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001m-9000000000-fb80dcbab23323a042af2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-2416d7f64101b9473cbb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-2900000000-ad1f1fabdf6b1579fff72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0005-9400000000-708e258e692a0abfbc922017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9100000000-7d75e23ae6944c1e9c6d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001m-9000000000-fb80dcbab23323a042af2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1900000000-76ae33b45e4348d50b072017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-02bf-7900000000-665940e67ad40f7590482021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-053i-9800000000-0f708ba46e75f553e77c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00dl-5900000000-86f6d19bba9a914d22ee2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0159-0900000000-a1a6bf5b3a0ac3863c902021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-06ur-9700000000-18795e8a2dc93ca36a932021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08gr-0900000000-be3cb913118057f499d12015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06rj-0900000000-6bebea0fda2ef3a2263b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-6900000000-ede11b81a97e891c66e32015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-2584f872c980915c17392015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01s9-1900000000-249c71cfa9cefe2a80202015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-3900000000-66991d861a91be9b92862015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference