Milk Composition Database: Showing metabocard for 4-Hydroxyphenylpyruvic acid (BMDB0000707)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:35:13 UTC

Update Date

2020-05-21 16:28:47 UTC

MCDB ID

BMDB0000707

Secondary Accession Numbers

BMDB00707

Metabolite Identification

Common Name

4-Hydroxyphenylpyruvic acid

Description

4-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 exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 4-Hydroxyphenylpyruvic acid exists in all living species, ranging from bacteria to humans. 4-Hydroxyphenylpyruvic acid is a potentially toxic compound.

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 )

Physical Properties

State

Solid

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	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	2014-06-16	View 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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-002o-5910000000-fd1e55c84c79bfeca559	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-002f-1941000000-2b4c87544657895fcaf6	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-014i-3492100000-483bdcea11d60fe4d306	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-014i-6791000000-ddc0a3b695cd1d0769f2	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002f-1951000000-ecd071a64b26ca77684c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-002f-1920000000-75b07d9c09371340939f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-9340000000-087aad2497b3493d27c0	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-002o-5910000000-fd1e55c84c79bfeca559	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-002f-1941000000-2b4c87544657895fcaf6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-3492100000-483bdcea11d60fe4d306	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-6791000000-ddc0a3b695cd1d0769f2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-2920000000-469469dfaad745fa78e8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-002o-2910000000-4f336335a2366e7dd6db	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6900000000-91bfe3ee54a36877251b	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0adi-6961000000-670161f1542fda9ff1fe	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0a4i-0900000000-12033042c41b550bed42	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-0900000000-6e8a3701c6d254cc824d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0560-1900000000-8082c68e259d24234d05	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-2416d7f64101b9473cbb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-2900000000-b4c21b3d9751b9e56d67	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0005-9400000000-708e258e692a0abfbc92	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9100000000-7d75e23ae6944c1e9c6d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001m-9000000000-fb80dcbab23323a042af	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-2416d7f64101b9473cbb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-2900000000-ad1f1fabdf6b1579fff7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0005-9400000000-708e258e692a0abfbc92	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9100000000-7d75e23ae6944c1e9c6d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001m-9000000000-fb80dcbab23323a042af	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-1900000000-76ae33b45e4348d50b07	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-02bf-7900000000-665940e67ad40f759048	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-053i-9800000000-0f708ba46e75f553e77c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00dl-5900000000-86f6d19bba9a914d22ee	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0159-0900000000-a1a6bf5b3a0ac3863c90	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-06ur-9700000000-18795e8a2dc93ca36a93	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08gr-0900000000-be3cb913118057f499d1	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rj-0900000000-6bebea0fda2ef3a2263b	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-6900000000-ede11b81a97e891c66e3	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-2584f872c980915c1739	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01s9-1900000000-249c71cfa9cefe2a8020	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-3900000000-66991d861a91be9b9286	2015-04-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a59-5900000000-6c003e26816579df31ca	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View 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)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 23438684	details
Detected but not Quantified	Not Applicable		PMID: 28342601	details

External Links

HMDB ID

HMDB0000707

DrugBank ID

DB07718

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

P-HYDROXY-PHENYLPYRUVATE

BiGG ID

37006

Wikipedia Link

4-Hydroxyphenylpyruvic_acid

METLIN ID

5675

PubChem Compound

979

PDB ID

Not Available

ChEBI ID

15999

References

Synthesis Reference

Billek, Gerhard. p-Hydroxyphenylpyruvic acid. Organic Syntheses (1963), 43 49-54.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]

Showing metabocard for 4-Hydroxyphenylpyruvic acid (BMDB0000707)

Structure for BMDB0000707 (4-Hydroxyphenylpyruvic acid)