Record Information
Version1.0
Created at2020-04-17 18:44:09 UTC
Updated at2020-12-07 19:11:07 UTC
CannabisDB IDCDB004859
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4-Hydroxyphenylpyruvic acid
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. 4-Hydroxyphenylpyruvic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight180.16
Monoisotopic Molecular Weight180.0423
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 effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point219 - 220 °CNot 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)2.91ChemAxon
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a59-5900000000-6c003e26816579df31ca2014-09-20View Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrumsplash10-002f-1920000000-75b07d9c09371340939fSpectrum
GC-MS4-Hydroxyphenylpyruvic acid, 3 TMS, GC-MS Spectrumsplash10-00xr-9340000000-087aad2497b3493d27c0Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-002o-5910000000-fd1e55c84c79bfeca559Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-002f-1941000000-2b4c87544657895fcaf6Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, 1 MEOX; 3 TMS, GC-MS Spectrumsplash10-014i-3492100000-483bdcea11d60fe4d306Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, 1 MEOX; 3 TMS, GC-MS Spectrumsplash10-014i-6791000000-ddc0a3b695cd1d0769f2Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrumsplash10-002f-1951000000-ecd071a64b26ca77684cSpectrum
GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrumsplash10-002f-1920000000-75b07d9c09371340939fSpectrum
GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrumsplash10-00xr-9340000000-087aad2497b3493d27c0Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrumsplash10-002o-5910000000-fd1e55c84c79bfeca559Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrumsplash10-002f-1941000000-2b4c87544657895fcaf6Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrumsplash10-014i-3492100000-483bdcea11d60fe4d306Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrumsplash10-014i-6791000000-ddc0a3b695cd1d0769f2Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrumsplash10-0006-2920000000-469469dfaad745fa78e8Spectrum
GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, GC-MS Spectrumsplash10-002o-2910000000-4f336335a2366e7dd6dbSpectrum
Predicted GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-6900000000-91bfe3ee54a36877251bSpectrum
Predicted GC-MS4-Hydroxyphenylpyruvic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0adi-6961000000-670161f1542fda9ff1feSpectrum
Predicted GC-MS4-Hydroxyphenylpyruvic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxyphenylpyruvic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxyphenylpyruvic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxyphenylpyruvic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxyphenylpyruvic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxyphenylpyruvic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxyphenylpyruvic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Hydroxyphenylpyruvic acid, 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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Macrophage migration inhibitory factorMIF22q11.23P14174 details
Tyrosine aminotransferaseTAT16q22.1P17735 details
Aspartate aminotransferase, cytoplasmicGOT110q24.1-q25.1P17174 details
Aspartate aminotransferase, mitochondrialGOT216q21P00505 details
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
4-hydroxyphenylpyruvate dioxygenaseHPD12q24-qterP32754 details
L-amino-acid oxidaseIL4I119q13.3-q13.4Q96RQ9 details
Sulfotransferase 1A3SULT1A3P0DMM9 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
4-hydroxyphenylpyruvate dioxygenaseHPD12q24-qterP32754 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Macrophage migration inhibitory factorMIF22q11.23P14174 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000707
DrugBank IDDB07718
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

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
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
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
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
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
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
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
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