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	ZINC000263614187

Download	Molfile XML SDF

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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

-0.9449 0.0866 0.5151 C 0 0 0 0 0 0 0 0 0 0 0 0

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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3 6 2 0 0 0 0

5 3 1 0 0 0 0

4 1 1 0 0 0 0

5 7 1 0 0 0 0

5 8 1 0 0 0 0

5 9 1 0 0 0 0

4 10 1 0 0 0 0

M END): 18 ms

reading 10 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

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Wikipedia	License
Testosterone is the primary male sex hormone and androgen in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testicles and prostate, as well as promoting secondary sexual characteristics such as increased muscle and bone mass, and the growth of body hair. It is associated with increased aggression, sex drive, dominance, courtship display, and a wide range of behavioral characteristics. In addition, testosterone in both sexes is involved in health and well-being, where it has a significant effect on overall mood, cognition, social and sexual behavior, metabolism and energy output, the cardiovascular system, and in the prevention of osteoporosis. Insufficient levels of testosterone in men may lead to abnormalities including frailty, accumulation of adipose fat tissue within the body, anxiety and depression, sexual performance issues, and bone loss. Excessive levels of testosterone in men may be associated with hyperandrogenism, higher risk of heart failure, increased mortality in men with prostate cancer, and male pattern baldness. Testosterone is a steroid hormone from the androstane class containing a ketone and a hydroxyl group at positions three and seventeen respectively. It is biosynthesized in several steps from cholesterol and is converted in the liver to inactive metabolites. It exerts its action through binding to and activation of the androgen receptor. In humans and most other vertebrates, testosterone is secreted primarily by the testicles of males and, to a lesser extent, the ovaries of females. On average, in adult males, levels of testosterone are about seven to eight times as great as in adult females. As the metabolism of testosterone in males is more pronounced, the daily production is about 20 times greater in men. Females are also more sensitive to the hormone. In addition to its role as a natural hormone, testosterone is used as a medication to treat hypogonadism and breast cancer. Since testosterone levels decrease as men age, testosterone is sometimes used in older men to counteract this deficiency. It is also used illicitly to enhance physique and performance, for instance in athletes. The World Anti-Doping Agency lists it as S1 Anabolic agent substance "prohibited at all times".
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	Types	Sources
11762589	PubMed citation	Europe PMC
19260671	PubMed citation	Europe PMC
22150460	PubMed citation	Europe PMC
22233273	PubMed citation	Europe PMC
22735334	PubMed citation	Europe PMC
22770225	PubMed citation	Europe PMC

Last Modified

18 April 2024

CHEBI:32816 - pyruvic acid

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