pyruvic acid (CHEBI:32816)

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CHEBI:32816 - pyruvic acid

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ChEBI Name	pyruvic acid

ChEBI ID	CHEBI:32816

Definition	A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45253, CHEBI:8685, CHEBI:26466

Supplier Information	ChemicalBook:CB54635331, ChemicalBook:CB5257557, eMolecules:478132, ZINC000001532517

Download	Molfile XML SDF

more structures >>

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10 9 0 0 0 0 999 V2000

1.3412 -0.0817 -0.4094 C 0 0 0 0 0 0 0 0 0 0 0 0

2.4392 -0.6183 -0.3675 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2405 -0.6588 0.1345 C 0 0 0 0 0 0 0 0 0 0 0 0

1.3198 1.0044 -0.9796 O 0 0 0 0 0 0 0 0 0 0 0 0

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0.2405 -1.8673 0.3367 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.7345 -0.5538 0.9164 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6860 0.8101 1.2911 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3618 0.6233 -0.3389 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5669 1.4448 -1.0985 H 0 0 0 0 0 0 0 0 0 0 0 0

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M END): 25 ms

reading 10 atoms

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Wikipedia	License
Pyruvic acid (CH3COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate base, CH3COCOO−, is an intermediate in several metabolic pathways throughout the cell. Pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or converted to fatty acids through a reaction with acetyl-CoA. It can also be used to construct the amino acid alanine and can be converted into ethanol or lactic acid via fermentation. Pyruvic acid supplies energy to cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactate when oxygen is lacking.
Read full article at Wikipedia

Formula

C3H4O3

Net Charge

Average Mass

88.06206

Monoisotopic Mass

88.01604

InChI

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

InChIKey

LCTONWCANYUPML-UHFFFAOYSA-N

SMILES

CC(=O)C(O)=O

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	fundamental metabolite Any metabolite produced by all living cells. cofactor An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	pyruvic acid (CHEBI:32816) has functional parent propionic acid (CHEBI:30768) pyruvic acid (CHEBI:32816) has role cofactor (CHEBI:23357) pyruvic acid (CHEBI:32816) has role fundamental metabolite (CHEBI:78675) pyruvic acid (CHEBI:32816) is a 2-oxo monocarboxylic acid (CHEBI:35910) pyruvic acid (CHEBI:32816) is conjugate acid of pyruvate (CHEBI:15361)

Incoming	β-(methylenecyclopropyl)pyruvic acid (CHEBI:133390) has functional parent pyruvic acid (CHEBI:32816) (2Z)-2-hydroxy-3-(3-methoxyphenyl)prop-2-enoic acid (CHEBI:193988) has functional parent pyruvic acid (CHEBI:32816) (2Z)-2-hydroxy-3-(4-methoxyphenyl)prop-2-enoic acid (CHEBI:193986) has functional parent pyruvic acid (CHEBI:32816) (3,5-diiodo-4-hydroxyphenyl)pyruvic acid (CHEBI:17131) has functional parent pyruvic acid (CHEBI:32816) (3E)-3-[(1R,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylidene]pyruvic acid (CHEBI:85358) has functional parent pyruvic acid (CHEBI:32816) (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid (CHEBI:59354) has functional parent pyruvic acid (CHEBI:32816) (3S)-3-methyl-2-oxo-3-phenylpropanoic acid (CHEBI:74122) has functional parent pyruvic acid (CHEBI:32816) (4-bromophenylsulfanyl)pyruvic acid (CHEBI:8934) has functional parent pyruvic acid (CHEBI:32816) (S)-3-hydroxy-2-oxo-3-phenylpropanoic acid (CHEBI:73985) has functional parent pyruvic acid (CHEBI:32816) 2-hydroxy-3-carboxybenzylidenepyruvic acid (CHEBI:19602) has functional parent pyruvic acid (CHEBI:32816) 2-hydroxy-3-methylbenzylidenepyruvic acid (CHEBI:19603) has functional parent pyruvic acid (CHEBI:32816) 2-hydroxy-4-hydroxymethylbenzylidenepyruvic acid (CHEBI:19610) has functional parent pyruvic acid (CHEBI:32816) 2-oxo-3-(3,4,5-trihydroxyphenyl)propanoic acid (CHEBI:190906) has functional parent pyruvic acid (CHEBI:32816) 2-oxo-3-(5-oxofuran-2-ylidene)propanoic acid (CHEBI:65114) has functional parent pyruvic acid (CHEBI:32816) 2-oxo-3-[4-(sulfooxy)phenyl]propanoic acid (CHEBI:169063) has functional parent pyruvic acid (CHEBI:32816) 3,4-dihydro-4-hydroxyphenylpyruvic acid (CHEBI:64939) has functional parent pyruvic acid (CHEBI:32816) 3,4-dihydroxyphenylpyruvic acid (CHEBI:19891) has functional parent pyruvic acid (CHEBI:32816) 3,5,3'-triiodothyropyruvic acid (CHEBI:18184) has functional parent pyruvic acid (CHEBI:32816) 3,5-dibromo-4-hydroxyphenylpyruvic acid (CHEBI:28128) has functional parent pyruvic acid (CHEBI:32816) 3,5-dichloro-4-hydroxyphenylpyruvic acid (CHEBI:28025) has functional parent pyruvic acid (CHEBI:32816) 3,5-dinitro-4-hydroxyphenylpyruvic acid (CHEBI:27981) has functional parent pyruvic acid (CHEBI:32816) 3-(2,4-dihydroxy-5-methoxyphenyl)-2-oxopropanoic acid (CHEBI:184410) has functional parent pyruvic acid (CHEBI:32816) 3-(3-methoxy-4-phenylmethoxyphenyl)-2-oxopropanoic acid (CHEBI:125489) has functional parent pyruvic acid (CHEBI:32816) 3-(3-methoxyphenyl)-2-oxopropanoic acid (CHEBI:193989) has functional parent pyruvic acid (CHEBI:32816) 3-(4-aminophenyl)pyruvic acid (CHEBI:143077) has functional parent pyruvic acid (CHEBI:32816) 3-(4-hydroxycyclohex-2-en-1-ylidene)pyruvic acid (CHEBI:64942) has functional parent pyruvic acid (CHEBI:32816) 3-(4-methoxyphenyl)-2-oxopropanoic acid (CHEBI:193985) has functional parent pyruvic acid (CHEBI:32816) 3-(5-benzyloxyindol-3-yl)pyruvic acid (CHEBI:55519) has functional parent pyruvic acid (CHEBI:32816) 3-(5-hydroxyindol-3-yl)pyruvic acid (CHEBI:27597) has functional parent pyruvic acid (CHEBI:32816) 3-(imidazol-1-yl)pyruvic acid (CHEBI:27501) has functional parent pyruvic acid (CHEBI:32816) 3-(imidazol-4-yl)pyruvic acid (CHEBI:59013) has functional parent pyruvic acid (CHEBI:32816) 3-(imidazol-5-yl)pyruvic acid (CHEBI:17406) has functional parent pyruvic acid (CHEBI:32816) 3-(indol-3-yl)pyruvic acid (CHEBI:29750) has functional parent pyruvic acid (CHEBI:32816) 3-[(1R,2S,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl]pyruvic acid (CHEBI:85359) has functional parent pyruvic acid (CHEBI:32816) 3-[3-methoxy-4-(sulfooxy)phenyl]-2-oxopropanoic acid (CHEBI:168858) has functional parent pyruvic acid (CHEBI:32816) 3-[4-hydroxy-3-(sulfooxy)phenyl]-2-oxopropanoic acid (CHEBI:169175) has functional parent pyruvic acid (CHEBI:32816) 3-[hydroxy(oxido)phosphoranyl]pyruvic acid (CHEBI:18007) has functional parent pyruvic acid (CHEBI:32816) 3-acylpyruvic acid (CHEBI:1447) has functional parent pyruvic acid (CHEBI:32816) 3-bromopyruvic acid (CHEBI:131461) has functional parent pyruvic acid (CHEBI:32816) 3-dimethylallyl-4-hydroxyphenylpyruvic acid (CHEBI:31113) has functional parent pyruvic acid (CHEBI:32816) 3-fluoropyruvic acid (CHEBI:55521) has functional parent pyruvic acid (CHEBI:32816) 3-fumarylpyruvic acid (CHEBI:1506) has functional parent pyruvic acid (CHEBI:32816) 3-hydroxyphenylpyruvic acid (CHEBI:167870) has functional parent pyruvic acid (CHEBI:32816) 3-hydroxypyruvic acid (CHEBI:30841) has functional parent pyruvic acid (CHEBI:32816) 3-mercaptopyruvic acid (CHEBI:16208) has functional parent pyruvic acid (CHEBI:32816) 3-phosphonooxypyruvic acid (CHEBI:30933) has functional parent pyruvic acid (CHEBI:32816) 3-phosphonopyruvic acid (CHEBI:30935) has functional parent pyruvic acid (CHEBI:32816) 3-sulfinylpyruvic acid (CHEBI:1665) has functional parent pyruvic acid (CHEBI:32816) 3-sulfopyruvic acid (CHEBI:16894) has functional parent pyruvic acid (CHEBI:32816) 4-hydroxy-3-iodophenylpyruvate (CHEBI:52989) has functional parent pyruvic acid (CHEBI:32816) 4-hydroxy-3-iodophenylpyruvic acid (CHEBI:28039) has functional parent pyruvic acid (CHEBI:32816) 4-hydroxyphenylpyruvic acid (CHEBI:15999) has functional parent pyruvic acid (CHEBI:32816) keto-phenylpyruvic acid (CHEBI:30851) has functional parent pyruvic acid (CHEBI:32816) Dimethoxycinnamic acid (CHEBI:176369) has functional parent pyruvic acid (CHEBI:32816) Hydroxyphenylpyruvic acid (CHEBI:167876) has functional parent pyruvic acid (CHEBI:32816) lignin cw compound-2040 (CHEBI:86735) has functional parent pyruvic acid (CHEBI:32816) lignin cw compound-2041 (CHEBI:86736) has functional parent pyruvic acid (CHEBI:32816) lignin cw compound-2042 (CHEBI:86737) has functional parent pyruvic acid (CHEBI:32816) lignin cw compound-3052 (CHEBI:86864) has functional parent pyruvic acid (CHEBI:32816) lignin cw compound-3056 (CHEBI:86867) has functional parent pyruvic acid (CHEBI:32816) Loniphenyruviridoside B, (rel)- (CHEBI:69639) has functional parent pyruvic acid (CHEBI:32816) Loniphenyruviridoside C (CHEBI:69640) has functional parent pyruvic acid (CHEBI:32816) Methyl 3-(4-methoxyphenyl)-2-oxopropanoate (CHEBI:173183) has functional parent pyruvic acid (CHEBI:32816) methyl pyruvate (CHEBI:51850) has functional parent pyruvic acid (CHEBI:32816) pyruvate ester (CHEBI:90320) has functional parent pyruvic acid (CHEBI:32816) Schizotenuin F (CHEBI:169046) has functional parent pyruvic acid (CHEBI:32816) tetrahydro-4-hydroxyphenylpyruvic acid (CHEBI:64808) has functional parent pyruvic acid (CHEBI:32816) Vanillactic acid (CHEBI:88526) has functional parent pyruvic acid (CHEBI:32816) pyruvate (CHEBI:15361) is conjugate base of pyruvic acid (CHEBI:32816) pyruvoyl group (CHEBI:45360) is substituent group from pyruvic acid (CHEBI:32816)

IUPAC Name

2-oxopropanoic acid

Synonyms

Sources

2-ketopropionic acid

ChemIDplus Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

2-oxopropanoic acid

ChEBI

2-Oxopropanoic acid

KEGG COMPOUND

2-Oxopropansäure Deutsch

ChemIDplus Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

2-Oxopropionsäure Deutsch

ChemIDplus Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

acetylformic acid

NIST Chemistry WebBook Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

Acetylformic acid

HMDB

acide pyruvique Français

ChEBI

α-ketopropionic acid

NIST Chemistry WebBook Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

α-Oxopropionsäure Deutsch

ChemIDplus Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

Brenztraubensäure Deutsch

ChEBI

BTS

Note: (2008-01-07) Acronym for Brenztraubensäure.

ChemIDplus

CH₃COCOOH

NIST Chemistry WebBook Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

Pyroracemic acid

KEGG COMPOUND

pyruvic acid

ChEBI

Pyruvic acid

KEGG COMPOUND

PYRUVIC ACID

PDBeChem

Manual Xrefs	Databases
C00001200	KNApSAcK
C00022	KEGG COMPOUND
DB00119	DrugBank
ECMDB00243	ECMDB
HMDB0000243	HMDB
LMFA01060077	LIPID MAPS
PYR	PDBeChem
PYRUVATE	MetaCyc
Pyruvic_acid	Wikipedia
YMDB00175	YMDB
View more database links

Registry Numbers	Types	Sources
101087	Gmelin Registry Number	Gmelin
127-17-3	CAS Registry Number	NIST Chemistry WebBook
127-17-3	CAS Registry Number	ChemIDplus
506211	Beilstein Registry Number	Beilstein
506211	Reaxys Registry Number	Reaxys

Citations

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]

Wells A, Osborne JP (2012)
Impact of acetaldehyde- and pyruvic acid-bound sulphur dioxide on wine lactic acid bacteria.
Letters in applied microbiology 54, 187-194 [PubMed:22150460]
[show Abstract]

Bordbar A, Mo ML, Nakayasu ES, Schrimpe-Rutledge AC, Kim YM, Metz TO, Jones MB, Frank BC, Smith RD, Peterson SN, Hyduke DR, Adkins JN, Palsson BO (2012)
Model-driven multi-omic data analysis elucidates metabolic immunomodulators of macrophage activation.
Molecular systems biology 8, 558 [PubMed:22735334]
[show Abstract]

Larsen MC, Vaida V (2012)
Near infrared photochemistry of pyruvic acid in aqueous solution.
The journal of physical chemistry. A 116, 5840-5846 [PubMed:22233273]
[show Abstract]

Plath KL, Takahashi K, Skodje RT, Vaida V (2009)
Fundamental and overtone vibrational spectra of gas-phase pyruvic acid.
The journal of physical chemistry. A 113, 7294-7303 [PubMed:19260671]
[show Abstract]

Li Y, Chen J, Lun SY (2001)
Biotechnological production of pyruvic acid.
Applied microbiology and biotechnology 57, 451-459 [PubMed:11762589]
[show Abstract]

Last Modified

18 April 2024

ChEBI

CHEBI:32816 - pyruvic acid

Aims

Methods and results

Conclusions

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