Livestock Metabolome Database: Showing metabocard for 4-Hydroxyphenylpyruvic acid (LMDB00224)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:05 UTC

Update Date

2016-07-20 20:58:20 UTC

Lmdb

LMDB00224

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Hydroxyphenylpyruvic acid

Description

4-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 ). There are two isomers of HPPA, specifically 4HPPA and 3HPPA, of which 4HPPA is the most common.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(4-Hydroxyphenyl)pyruvic acid	ChEBI
(p-Hydroxyphenyl)pyruvic acid	ChEBI
3-(4-HYDROXY-phenyl)pyruvIC ACID	ChEBI
3-(4-Hydroxyphenyl)pyruvic acid	ChEBI
3-(p-Hydroxyphenyl)-2-oxopropanoic acid	ChEBI
4-Hydroxy alpha-oxobenzenepropanoic acid	ChEBI
p-Hydroxyphenylpyruvic acid	ChEBI
4-Hydroxyphenylpyruvate	Kegg
(4-Hydroxyphenyl)pyruvate	Generator
(p-Hydroxyphenyl)pyruvate	Generator
3-(4-HYDROXY-phenyl)pyruvate	Generator
3-(4-Hydroxyphenyl)pyruvate	Generator
3-(p-Hydroxyphenyl)-2-oxopropanoate	Generator
4-Hydroxy a-oxobenzenepropanoate	Generator
4-Hydroxy a-oxobenzenepropanoic acid	Generator
4-Hydroxy alpha-oxobenzenepropanoate	Generator
4-Hydroxy α-oxobenzenepropanoate	Generator
4-Hydroxy α-oxobenzenepropanoic acid	Generator
p-Hydroxyphenylpyruvate	Generator
(p-Hydroxyphenyl)-pyruvate	HMDB
(p-Hydroxyphenyl)-pyruvic acid	HMDB
3-(4-Hydroxyphenyl)-2-oxo-propanoate	HMDB
3-(4-Hydroxyphenyl)-2-oxo-propanoic acid	HMDB
3-(4-Hydroxyphenyl)-2-oxopropionate	HMDB
3-(4-Hydroxyphenyl)-2-oxopropionic acid	HMDB
3-(p-Hydroxyphenyl)-2-oxopropionate	HMDB
3-(p-Hydroxyphenyl)-2-oxopropionic acid	HMDB
3-(p-Hydroxyphenyl)pyruvate	HMDB
3-(p-Hydroxyphenyl)pyruvic acid	HMDB
4-Hydroxy-a-oxobenzenepropanoate	HMDB
4-Hydroxy-a-oxobenzenepropanoic acid	HMDB
4-Hydroxy-alpha-oxobenzenepropanoate	HMDB
4-Hydroxy-alpha-oxobenzenepropanoic acid	HMDB
4HPPA	HMDB
HPPA	HMDB
Hydroxyphenylpyruvate	HMDB
Hydroxyphenylpyruvic acid	HMDB
p-Hydroxyphenylpyruvic	HMDB
Testacid	HMDB
4-Hydroxyphenylpyruvic acid, ion	HMDB
4-Hydroxyphenylpyruvic acid, sodium salt	HMDB
Para-hydroxyphenylpyruvic acid	HMDB

Chemical Formula

C₉H₈O₄

Average Molecular Weight

180.1574

Monoisotopic Molecular Weight

180.042258744

IUPAC Name

3-(4-hydroxyphenyl)-2-oxopropanoic acid

Traditional Name

4-hydroxyphenylpyruvic acid

CAS Registry Number

156-39-8

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 Key

KKADPXVIOXHVKN-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpyruvic acid derivatives

Direct Parent

Phenylpyruvic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:15999 )
oxo carboxylic acid (CHEBI:15999 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.12	ALOGPS
logP	1.6	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.69 m³·mol⁻¹	ChemAxon
Polarizability	16.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-002f-1920000000-75b07d9c09371340939f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00xr-9340000000-087aad2497b3493d27c0	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-002o-5910000000-fd1e55c84c79bfeca559	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-002f-1941000000-2b4c87544657895fcaf6	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-014i-3492100000-483bdcea11d60fe4d306	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-014i-6791000000-ddc0a3b695cd1d0769f2	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002f-1951000000-ecd071a64b26ca77684c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-002f-1920000000-75b07d9c09371340939f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-9340000000-087aad2497b3493d27c0	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-002o-5910000000-fd1e55c84c79bfeca559	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-002f-1941000000-2b4c87544657895fcaf6	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-3492100000-483bdcea11d60fe4d306	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-6791000000-ddc0a3b695cd1d0769f2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-2920000000-469469dfaad745fa78e8	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-002o-2910000000-4f336335a2366e7dd6db	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6900000000-91bfe3ee54a36877251b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0adi-6961000000-670161f1542fda9ff1fe	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0a4i-0900000000-12033042c41b550bed42	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-0900000000-6e8a3701c6d254cc824d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0560-1900000000-8082c68e259d24234d05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-2416d7f64101b9473cbb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-2900000000-b4c21b3d9751b9e56d67	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0005-9400000000-708e258e692a0abfbc92	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9100000000-7d75e23ae6944c1e9c6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001m-9000000000-fb80dcbab23323a042af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-2416d7f64101b9473cbb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-2900000000-ad1f1fabdf6b1579fff7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0005-9400000000-708e258e692a0abfbc92	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9100000000-7d75e23ae6944c1e9c6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001m-9000000000-fb80dcbab23323a042af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-1900000000-76ae33b45e4348d50b07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-02bf-7900000000-665940e67ad40f759048	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-053i-9800000000-0f708ba46e75f553e77c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00dl-5900000000-86f6d19bba9a914d22ee	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0159-0900000000-a1a6bf5b3a0ac3863c90	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-06ur-9700000000-18795e8a2dc93ca36a93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08gr-0900000000-be3cb913118057f499d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rj-0900000000-6bebea0fda2ef3a2263b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-6900000000-ede11b81a97e891c66e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-2584f872c980915c1739	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01s9-1900000000-249c71cfa9cefe2a8020	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-3900000000-66991d861a91be9b9286	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a59-5900000000-6c003e26816579df31ca	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details

External Links

DrugBank ID

DB07718

HMDB ID

HMDB0000707

FooDB ID

FDB030506

Phenol Explorer ID

Not Available

KNApSAcK ID

C00007512

BiGG ID

37006

BioCyc ID

P-HYDROXY-PHENYLPYRUVATE

METLIN ID

5675

PDB ID

Not Available

Wikipedia Link

4-Hydroxyphenylpyruvic_acid

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [11073718 ]

Showing metabocard for 4-Hydroxyphenylpyruvic acid (LMDB00224)

Structure for LMDB00224 (4-Hydroxyphenylpyruvic acid)