Milk Composition Database: Showing metabocard for Pyruvic acid (BMDB0000243)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:17 UTC

Update Date

2020-06-04 20:48:59 UTC

MCDB ID

BMDB0000243

Secondary Accession Numbers

BMDB00243

Metabolite Identification

Common Name

Pyruvic acid

Description

Pyruvic acid, also known as pyroracemic acid or 2-oxopropanoate, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Pyruvic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Pyruvic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Pyruvic acid exists in all living species, ranging from bacteria to humans. Pyruvic acid is a potentially toxic compound. Pyruvic acid has been found to be associated with several diseases known as leigh's syndrome, subacute necrotizing encephalopathy, sne, myopathy with lactic acidosis, hereditary, and 3-hydroxy-3-methylglutaryl-coa synthase deficiency; also pyruvic acid has been linked to several inborn metabolic disorders including 3-methylglutaconic aciduria type ii, x-linked and glucagon deficiency.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Ketopropionic acid	ChEBI
2-Oxopropanoic acid	ChEBI
2-Oxopropansaeure	ChEBI
2-Oxopropionsaeure	ChEBI
Acetylformic acid	ChEBI
Acide pyruvique	ChEBI
alpha-Ketopropionic acid	ChEBI
alpha-Oxopropionsaeure	ChEBI
Brenztraubensaeure	ChEBI
BTS	ChEBI
CH3COCOOH	ChEBI
Pyroracemic acid	ChEBI
2-Oxopropanoate	Kegg
2-Ketopropionate	Generator
Acetylformate	Generator
a-Ketopropionate	Generator
a-Ketopropionic acid	Generator
alpha-Ketopropionate	Generator
Α-ketopropionate	Generator
Α-ketopropionic acid	Generator
a-Oxopropionsaeure	Generator
Α-oxopropionsaeure	Generator
Pyroracemate	Generator
Pyruvate	Generator
2-Oxopropionate	HMDB
2-Oxopropionic acid	HMDB
Acid, pyruvic	MeSH, HMDB
Pyruvic acid	HMDB
alpha-Ketopropanoic acid	HMDB
α-Ketopropanoic acid	HMDB

Chemical Formula

C₃H₄O₃

Average Molecular Weight

88.0621

Monoisotopic Molecular Weight

88.016043994

IUPAC Name

2-oxopropanoic acid

Traditional Name

pyruvic acid

CAS Registry Number

127-17-3

SMILES

CC(=O)C(O)=O

InChI Identifier

InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)

InChI Key

LCTONWCANYUPML-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Alpha-keto acids and derivatives

Direct Parent

Alpha-keto acids and derivatives

Alternative Parents

Substituents

Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:32816 )
Oxo fatty acids (LMFA01060077 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	13.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.38	ALOGPS
logP	0.066	ChemAxon
logS	0.18	ALOGPS
pKa (Strongest Acidic)	2.93	ChemAxon
pKa (Strongest Basic)	-9.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	17.99 m³·mol⁻¹	ChemAxon
Polarizability	7.31 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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)	splash10-00dr-4900000000-f26ef76666e40ab9fe61	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-00di-5900000000-b8e81f82572d4796e944	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-5970000000-154bf9ad168a12593fcc	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-a2cf85a5e1d2379d26df	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-4900000000-f26ef76666e40ab9fe61	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-5900000000-b8e81f82572d4796e944	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-5970000000-154bf9ad168a12593fcc	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-5900000000-5b1f470d4ff91420618c	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-5417b44aa241a7ba27e8	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dm-9400000000-6db65a709bdc47e3adf7	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 (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 (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 - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-a2cf85a5e1d2379d26df	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-dd49835da8355fb6e625	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-f09d8e3d7a774b255d89	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9000000000-7d91f6f626cab1a366fd	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-8ae98cdb3e142034e52a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-e04e6c68013983e1b6dc	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-dd49835da8355fb6e625	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-f09d8e3d7a774b255d89	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-7d91f6f626cab1a366fd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-8ae98cdb3e142034e52a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-e04e6c68013983e1b6dc	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000f-9000000000-f24c93ecfd3928827154	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0udj-9000000000-fc3b9ad0c57f44261fba	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-f3444f8b94ee5a0a9f74	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-0avr-9000000000-dc40a6a1b9b166d6e68a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-016r-9000000000-efac7b176bb77118ecb8	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-d0defa72b09503c6d6d1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-9000000000-c25fa150e9c490319a2a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ccb42b4c05ddd001990f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-faf36ff70d6205370270	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-60c1a02aabf80f51050f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-ca5f4a2f06787d8b62a0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-0eb1fb2cdd24bdc78601	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-87bbaed151efac084591	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-87bbaed151efac084591	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-f315d0752893e7d0c657	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	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, 300 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	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
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	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 and Quantified	57.3 uM	PMID: 2760296	details
Detected and Quantified	2 - 188 uM	PMID: 20338431	details
Detected but not Quantified	Not Applicable	PMID: 23438684	details
Detected and Quantified	17 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	20 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	17 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	20 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	36 +/- 15 uM	PMID: 29642378	details
Detected and Quantified	32 +/- 8.44 uM	PMID: 29642378	details
Detected and Quantified	38 +/- 8.02 uM	PMID: 29642378	details
Detected and Quantified	24 +/- 29 uM	PMID: 23931703	details

External Links

HMDB ID

HMDB0000243

DrugBank ID

DB00119

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB031141

KNApSAcK ID

C00001200

Chemspider ID

Not Available

KEGG Compound ID

C00022

BioCyc ID

PYRUVATE

BiGG ID

Not Available

Wikipedia Link

Pyruvic_acid

METLIN ID

Not Available

PubChem Compound

1060

PDB ID

Not Available

ChEBI ID

32816

References

Synthesis Reference

Xiang, Wei; Okita, Motomu. Preparation of pyruvic acid. Jpn. Kokai Tokkyo Koho (2003), 5 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83. [PubMed:2760296 ]
Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
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 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug 23. [PubMed:23931703 ]
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for Pyruvic acid (BMDB0000243)

Structure for BMDB0000243 (Pyruvic acid)