Livestock Metabolome Database: Showing metabocard for Pyruvic acid (LMDB00112)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:37 UTC

Update Date

2021-04-30 20:57:58 UTC

Lmdb

LMDB00112

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pyruvic acid

Description

Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).

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 )

Ontology

Status

Detected and 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	-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	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)	splash10-00dr-4900000000-f26ef76666e40ab9fe61	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-00di-5900000000-b8e81f82572d4796e944	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-5970000000-154bf9ad168a12593fcc	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-a2cf85a5e1d2379d26df	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-4900000000-f26ef76666e40ab9fe61	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-5900000000-b8e81f82572d4796e944	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-5970000000-154bf9ad168a12593fcc	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-5900000000-5b1f470d4ff91420618c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-5417b44aa241a7ba27e8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dm-9400000000-6db65a709bdc47e3adf7	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 (Non-derivatized) - 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 (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 - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-a2cf85a5e1d2379d26df	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-dd49835da8355fb6e625	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-f09d8e3d7a774b255d89	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9000000000-7d91f6f626cab1a366fd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-8ae98cdb3e142034e52a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-e04e6c68013983e1b6dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-dd49835da8355fb6e625	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-f09d8e3d7a774b255d89	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-7d91f6f626cab1a366fd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-8ae98cdb3e142034e52a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-e04e6c68013983e1b6dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000f-9000000000-f24c93ecfd3928827154	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0udj-9000000000-fc3b9ad0c57f44261fba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9000000000-f3444f8b94ee5a0a9f74	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-0avr-9000000000-dc40a6a1b9b166d6e68a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 33V, Negative	splash10-016r-9000000000-efac7b176bb77118ecb8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-d0defa72b09503c6d6d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-9000000000-c25fa150e9c490319a2a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ccb42b4c05ddd001990f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-faf36ff70d6205370270	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-60c1a02aabf80f51050f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-ca5f4a2f06787d8b62a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-0eb1fb2cdd24bdc78601	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-87bbaed151efac084591	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-87bbaed151efac084591	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-f315d0752893e7d0c657	Spectrum
1D NMR	13C NMR Spectrum	Not Available	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
1D NMR	1H NMR Spectrum	Not Available	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
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H 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

Kidney perfusate
Milk
Plasma
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Kidney perfusate	Detected but not Quantified	Not Applicable	Not Available	Porcine	25502759	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Milk	Detected and Quantified	2-188 uM	Not Available	Bovine	20338431	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	21859467	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	22242129	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	21496096	details
Serum	Detected and Quantified	75.5292 +/- 27.4786 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	72.2206 +/- 25.8504 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	95.4965 +/- 37.7377 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	93.0998 +/- 21.9312 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	88.5155 +/- 36.2373 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	74.1914 +/- 27.0193 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	92.8532 +/- 31.9096 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	79.731 +/- 33.9397 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	67.22 +/- 30.06 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	79.4106 +/- 34.1811 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	63.6618 +/- 20.5312 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	81.7588 +/- 39.4988 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21942754	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	26020888	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21584308	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected and Quantified	81.7556 +/- 28.9683 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21429726	details
Serum	Detected and Quantified	87.4524 +/- 28.8199 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	69.61 +/- 20.5526 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	71.9101 +/- 23.1035 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	84.0034 +/- 34.2403 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	71.1684 +/- 27.9301 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	75.7639 +/- 15.5665 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	82.7807 +/- 26.2653 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	91.0729 +/- 38.4339 uM	Normal	Ovine	Goldansaz et al.,...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	22436164	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	24696864	details