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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:56 UTC
HMDB IDHMDB0000707
Secondary Accession Numbers
  • HMDB00707
Metabolite Identification
Common Name4-Hydroxyphenylpyruvic acid
Description4-Hydroxyphenylpyruvic acid (4-HPPA) is a keto acid that is involved in the tyrosine catabolism pathway. It is a product of the enzyme (R)-4-hydroxyphenyllactate dehydrogenase (EC 1.1.1.222) and is formed during tyrosine metabolism. The conversion from tyrosine to 4-HPPA is catalyzed by tyrosine aminotransferase. Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment. The enzyme 4-hydroxyphenylpyruvic acid dioxygenase (HPD) catalyzes the reaction that converts 4-hydroxyphenylpyruvic acid to homogentisic acid. A deficiency in the catalytic activity of HPD is known to lead to tyrosinemia type III, an autosomal recessive disorder characterized by elevated levels of blood tyrosine and massive excretion of tyrosine derivatives into urine. It has been shown that hawkinsinuria, an autosomal dominant disorder characterized by the excretion of 'hawkinsin,' may also be a result of HPD deficiency (PMID: 11073718 ). Moreover, 4-hydroxyphenylpyruvic acid is also found to be associated in phenylketonuria, which is also an inborn error of metabolism. There are two isomers of HPPA, specifically 4HPPA and 3HPPA, of which 4HPPA is the most common. 4-HPPA has been found to be a microbial metabolite in Escherichia (ECMDB).
Structure
Data?1676999705
Synonyms
ValueSource
(4-Hydroxyphenyl)pyruvic acidChEBI
(p-Hydroxyphenyl)pyruvic acidChEBI
3-(4-HYDROXY-phenyl)pyruvIC ACIDChEBI
3-(4-Hydroxyphenyl)pyruvic acidChEBI
3-(p-Hydroxyphenyl)-2-oxopropanoic acidChEBI
4-Hydroxy alpha-oxobenzenepropanoic acidChEBI
p-Hydroxyphenylpyruvic acidChEBI
4-HydroxyphenylpyruvateKegg
(4-Hydroxyphenyl)pyruvateGenerator
(p-Hydroxyphenyl)pyruvateGenerator
3-(4-HYDROXY-phenyl)pyruvateGenerator
3-(4-Hydroxyphenyl)pyruvateGenerator
3-(p-Hydroxyphenyl)-2-oxopropanoateGenerator
4-Hydroxy a-oxobenzenepropanoateGenerator
4-Hydroxy a-oxobenzenepropanoic acidGenerator
4-Hydroxy alpha-oxobenzenepropanoateGenerator
4-Hydroxy α-oxobenzenepropanoateGenerator
4-Hydroxy α-oxobenzenepropanoic acidGenerator
p-HydroxyphenylpyruvateGenerator
(p-Hydroxyphenyl)-pyruvateHMDB
(p-Hydroxyphenyl)-pyruvic acidHMDB
3-(4-Hydroxyphenyl)-2-oxo-propanoateHMDB
3-(4-Hydroxyphenyl)-2-oxo-propanoic acidHMDB
3-(4-Hydroxyphenyl)-2-oxopropionateHMDB
3-(4-Hydroxyphenyl)-2-oxopropionic acidHMDB
3-(p-Hydroxyphenyl)-2-oxopropionateHMDB
3-(p-Hydroxyphenyl)-2-oxopropionic acidHMDB
3-(p-Hydroxyphenyl)pyruvateHMDB
3-(p-Hydroxyphenyl)pyruvic acidHMDB
4-Hydroxy-a-oxobenzenepropanoateHMDB
4-Hydroxy-a-oxobenzenepropanoic acidHMDB
4-Hydroxy-alpha-oxobenzenepropanoateHMDB
4-Hydroxy-alpha-oxobenzenepropanoic acidHMDB
4HPPAHMDB
HPPAHMDB
HydroxyphenylpyruvateHMDB
Hydroxyphenylpyruvic acidHMDB
p-HydroxyphenylpyruvicHMDB
TestacidHMDB
4-Hydroxyphenylpyruvic acid, ionHMDB
4-Hydroxyphenylpyruvic acid, sodium saltHMDB
Para-hydroxyphenylpyruvic acidHMDB
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name3-(4-hydroxyphenyl)-2-oxopropanoic acid
Traditional Name4-hydroxyphenylpyruvic acid
CAS Registry Number156-39-8
SMILES
OC(=O)C(=O)CC1=CC=C(O)C=C1
InChI Identifier
InChI=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
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-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 effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point219 - 220 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker145.74630932474
[M-H]-Not Available145.746http://allccs.zhulab.cn/database/detail?ID=AllCCS00001915
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.2831661259
DarkChem[M+H]+140.2831661259
DarkChem[M-H]-137.78631661259
DarkChem[M-H]-137.78631661259
AllCCS[M+H]+138.18432859911
AllCCS[M-H]-136.31232859911
DeepCCS[M+H]+137.04930932474
DeepCCS[M-H]-134.65430932474
DeepCCS[M-2H]-169.99630932474
DeepCCS[M+Na]+144.47130932474
AllCCS[M+H]+138.232859911
AllCCS[M+H-H2O]+133.932859911
AllCCS[M+NH4]+142.232859911
AllCCS[M+Na]+143.332859911
AllCCS[M-H]-136.332859911
AllCCS[M+Na-2H]-137.032859911
AllCCS[M+HCOO]-137.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxyphenylpyruvic acidOC(=O)C(=O)CC1=CC=C(O)C=C13200.8Standard polar33892256
4-Hydroxyphenylpyruvic acidOC(=O)C(=O)CC1=CC=C(O)C=C11281.3Standard non polar33892256
4-Hydroxyphenylpyruvic acidOC(=O)C(=O)CC1=CC=C(O)C=C11787.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyphenylpyruvic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CC1=CC=C(O)C=C11824.8Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC(=O)C(=O)O)C=C11839.9Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,1TMS,isomer #3C[Si](C)(C)OC(=CC1=CC=C(O)C=C1)C(=O)O2025.2Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(=O)CC1=CC=C(O[Si](C)(C)C)C=C11882.9Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(=CC1=CC=C(O)C=C1)O[Si](C)(C)C2053.6Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,2TMS,isomer #3C[Si](C)(C)OC(=CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O2088.7Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C2071.8Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C2014.1Standard non polar33892256
4-Hydroxyphenylpyruvic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C2015.1Standard polar33892256
4-Hydroxyphenylpyruvic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CC=C(O)C=C12094.5Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)C(=O)O)C=C12121.6Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC1=CC=C(O)C=C1)C(=O)O2278.9Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12382.7Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C2529.5Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O2596.6Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2764.6Semi standard non polar33892256
4-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2665.0Standard non polar33892256
4-Hydroxyphenylpyruvic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2386.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-002f-1920000000-75b07d9c09371340939f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00xr-9340000000-087aad2497b3493d27c02014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (1 MEOX; 2 TMS)splash10-002o-5910000000-fd1e55c84c79bfeca5592014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (1 MEOX; 2 TMS)splash10-002f-1941000000-2b4c87544657895fcaf62014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (1 MEOX; 3 TMS)splash10-014i-3492100000-483bdcea11d60fe4d3062014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (1 MEOX; 3 TMS)splash10-014i-6791000000-ddc0a3b695cd1d0769f22014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid EI-B (Non-derivatized)splash10-002f-1951000000-ecd071a64b26ca77684c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Non-derivatized)splash10-002f-1920000000-75b07d9c09371340939f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Non-derivatized)splash10-00xr-9340000000-087aad2497b3493d27c02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized)splash10-002o-5910000000-fd1e55c84c79bfeca5592017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized)splash10-002f-1941000000-2b4c87544657895fcaf62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized)splash10-014i-3492100000-483bdcea11d60fe4d3062017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized)splash10-014i-6791000000-ddc0a3b695cd1d0769f22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Non-derivatized)splash10-0006-2920000000-469469dfaad745fa78e82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-EI-TOF (Non-derivatized)splash10-002o-2910000000-4f336335a2366e7dd6db2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6900000000-91bfe3ee54a36877251b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0adi-6961000000-670161f1542fda9ff1fe2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenylpyruvic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a59-5900000000-6c003e26816579df31ca2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0a4i-0900000000-12033042c41b550bed422012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0a4i-0900000000-6e8a3701c6d254cc824d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0560-1900000000-8082c68e259d24234d052012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-004i-0900000000-2416d7f64101b9473cbb2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0a4i-2900000000-b4c21b3d9751b9e56d672012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0005-9400000000-708e258e692a0abfbc922012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0002-9100000000-7d75e23ae6944c1e9c6d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-001m-9000000000-fb80dcbab23323a042af2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ , negative-QTOFsplash10-004i-0900000000-2416d7f64101b9473cbb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-2900000000-ad1f1fabdf6b1579fff72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ , negative-QTOFsplash10-0005-9400000000-708e258e692a0abfbc922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ , negative-QTOFsplash10-0002-9100000000-7d75e23ae6944c1e9c6d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid LC-ESI-QQ , negative-QTOFsplash10-001m-9000000000-fb80dcbab23323a042af2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid , positive-QTOFsplash10-001i-1900000000-76ae33b45e4348d50b072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 10V, Negative-QTOFsplash10-02bf-7900000000-665940e67ad40f7590482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 20V, Negative-QTOFsplash10-053i-9800000000-0f708ba46e75f553e77c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 35V, Negative-QTOFsplash10-00dl-5900000000-86f6d19bba9a914d22ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 35V, Positive-QTOFsplash10-0159-0900000000-a1a6bf5b3a0ac3863c902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 40V, Negative-QTOFsplash10-06ur-9700000000-18795e8a2dc93ca36a932021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 10V, Positive-QTOFsplash10-08gr-0900000000-be3cb913118057f499d12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 20V, Positive-QTOFsplash10-06rj-0900000000-6bebea0fda2ef3a2263b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 40V, Positive-QTOFsplash10-0a6r-6900000000-ede11b81a97e891c66e32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 10V, Negative-QTOFsplash10-004i-0900000000-2584f872c980915c17392015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 20V, Negative-QTOFsplash10-01s9-1900000000-249c71cfa9cefe2a80202015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenylpyruvic acid 40V, Negative-QTOFsplash10-001l-3900000000-66991d861a91be9b92862015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart 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 Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.37 +/- 0.23 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.65 (0.15-8.74) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.66 (0.23-2.50) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified4.9 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.6 (0.1-21.3) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified1.8 (0.1-4.5) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.5 (0.6-3.4) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.8 (1.2-4.3) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified150.31(60.04-507.20) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
details
UrineDetected and Quantified10.669 +/- 16.944 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified20.0820 +/- 49.577 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified9.413 +/- 18.199 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
UrineDetected and Quantified12 umol/mmol creatinineNewborn (0-30 days old)FemaleDeafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Cardiosvacular risk
details
UrineDetected and Quantified0 - 3.4 umol/mmol creatinineNewborn (0-30 days old)BothHawkinsinuria details
UrineDetected and Quantified102.8 -537.4 umol/mmol creatinineNewborn (0-30 days old)BothHawkinsinuria details
UrineDetected and Quantified2.447 +/- 20.710 umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria details
UrineDetected and Quantified33.261 +/- 20.0820 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
UrineDetected and Quantified24.00 +/- 30.5 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
UrineDetected and Quantified33.261 +/- 26.985 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Phenylketonuria
  1. Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
  2. Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
Hawkinsinuria
  1. Thodi G, Schulpis KH, Dotsikas Y, Pavlides C, Molou E, Chatzidaki M, Triantafylli O, Loukas YL: Hawkinsinuria in two unrelated Greek newborns: identification of a novel variant, biochemical findings and treatment. J Pediatr Endocrinol Metab. 2016 Jan;29(1):15-20. doi: 10.1515/jpem-2015-0132. [PubMed:26226126 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome
  1. James AW, Miranda SG, Culver K, Hall BD, Golabi M: DOOR syndrome: clinical report, literature review and discussion of natural history. Am J Med Genet A. 2007 Dec 1;143A(23):2821-31. doi: 10.1002/ajmg.a.32054. [PubMed:17994565 ]
Associated OMIM IDs
  • 114500 (Colorectal cancer)
  • 261600 (Phenylketonuria)
  • 140350 (Hawkinsinuria)
  • 220500 (Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome)
DrugBank IDDB07718
Phenol Explorer Compound IDNot Available
FooDB IDFDB030506
KNApSAcK IDC00007512
Chemspider ID954
KEGG Compound IDC01179
BioCyc IDP-HYDROXY-PHENYLPYRUVATE
BiGG ID37006
Wikipedia Link4-Hydroxyphenylpyruvic_acid
METLIN ID5675
PubChem Compound979
PDB IDNot Available
ChEBI ID15999
Food Biomarker OntologyNot Available
VMH ID34HPP
MarkerDB IDMDB00000229
Good Scents IDNot Available
References
Synthesis ReferenceBillek, Gerhard. p-Hydroxyphenylpyruvic acid. Organic Syntheses (1963), 43 49-54.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tomoeda K, Awata H, Matsuura T, Matsuda I, Ploechl E, Milovac T, Boneh A, Scott CR, Danks DM, Endo F: Mutations in the 4-hydroxyphenylpyruvic acid dioxygenase gene are responsible for tyrosinemia type III and hawkinsinuria. Mol Genet Metab. 2000 Nov;71(3):506-10. [PubMed:11073718 ]
  2. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  3. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  4. Endo F, Katoh H, Yamamoto S, Matsuda I: A murine model for type III tyrosinemia: lack of immunologically detectable 4-hydroxyphenylpyruvic acid dioxygenase enzyme protein in a novel mouse strain with hypertyrosinemia. Am J Hum Genet. 1991 Apr;48(4):704-9. [PubMed:2014797 ]
  5. Shoda J, Tanaka N, Osuga T, Matsuura K, Miyazaki H: Altered bile acid metabolism in liver disease: concurrent occurrence of C-1 and C-6 hydroxylated bile acid metabolites and their preferential excretion into urine. J Lipid Res. 1990 Feb;31(2):249-59. [PubMed:2324645 ]
  6. Wolff JA, Barshop B, Nyhan WL, Leslie J, Seegmiller JE, Gruber H, Garst M, Winter S, Michals K, Matalon R: Effects of ascorbic acid in alkaptonuria: alterations in benzoquinone acetic acid and an ontogenic effect in infancy. Pediatr Res. 1989 Aug;26(2):140-4. [PubMed:2771520 ]
  7. Deutsch JC: Determination of p-hydroxyphenylpyruvate, p-hydroxyphenyllactate and tyrosine in normal human plasma by gas chromatography-mass spectrometry isotope-dilution assay. J Chromatogr B Biomed Sci Appl. 1997 Mar 7;690(1-2):1-6. [PubMed:9106023 ]
  8. Muskiet FA, Fremouw-Ottevangers DC, Nagel GT, Wolthers BG, de Vries JA: Determination of 3-methoxy-4-hydroxyphenylpyruvic acid, 3,4-dihydroxyphenylethylene glycol, and 3,4-dihydroxyphenylmandelic acid in urine by mass fragmentography, with use of deuterium-labeled internal standards. Clin Chem. 1978 Nov;24(11):2001-8. [PubMed:709835 ]
  9. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in cell surface binding
Specific function:
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity.
Gene Name:
MIF
Uniprot ID:
P14174
Molecular weight:
12476.19
Reactions
4-Hydroxyphenylpyruvic acid → 2-Hydroxy-3-(4-hydroxyphenyl)propenoic aciddetails
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
Gene Name:
TAT
Uniprot ID:
P17735
Molecular weight:
50398.895
Reactions
L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + L-Glutamic aciddetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
Reactions
L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + L-Glutamic aciddetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + L-Glutamic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Hydroxyphenylpyruvic acid → 6-[4-(2-carboxy-2-oxoethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
4-Hydroxyphenylpyruvic acid → 3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-2-oxopropanoyl]oxy}oxane-2-carboxylic aciddetails
General function:
Involved in 4-hydroxyphenylpyruvate dioxygenase activity
Specific function:
Key enzyme in the degradation of tyrosine.
Gene Name:
HPD
Uniprot ID:
P32754
Molecular weight:
40497.105
Reactions
4-Hydroxyphenylpyruvic acid + Oxygen → Homogentisic acid + CO(2)details
4-Hydroxyphenylpyruvic acid + Oxygen → Homogentisic acid + Carbon dioxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name:
IL4I1
Uniprot ID:
Q96RQ9
Molecular weight:
65327.26
Reactions
L-Tyrosine + Water + Oxygen → 4-Hydroxyphenylpyruvic acid + Ammonia + Hydrogen peroxidedetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
4-Hydroxyphenylpyruvic acid → 2-oxo-3-[4-(sulfooxy)phenyl]propanoic aciddetails