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(2R,4S)-2-[(1R)-1-carboxy-2-hydroxy-2-methylpropyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 
(2S)-2-(4-\{[(1R,2S)-2-hydroxycyclopentyl]methyl\}phenyl)propanoic acid 
(2S)-2-[(2R,4S,5S)-3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-\{[(R)-hydroxy(phosphonooxy)phosphoryl]oxy\}ethyl)-4-methyl-1,3-thiazolidin-2-yl]-2-hydroxypropanoic acid 
(2S)-2-[3-(aminomethyl)phenyl]-3-[(S)-\{(1R)-1-[(2,1,3-benzothiadiazol-4-ylsulfonyl)amino]-2-methylpropyl\}(hydroxy)phosphoryl]propanoic acid 
(2S)-3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-(\{(3R)-1-[(1Z)-ethanimidoyl]pyrrolidin-3-yl\}oxy)phenyl]propanoic acid 
(2S)-3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-(\{1-[(1E)-ethanimidoyl]piperidin-4-yl\}oxy)phenyl]propanoic acid 
(3E)-3-[(1R,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylidene]pyruvic acid 
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid 
(3E)-4-(5-amino-2-hydroxyphenyl)-2-oxobut-3-enoic acid 
(3S)-3-methyl-2-oxo-3-phenylpropanoic acid 
(4-bromophenylsulfanyl)pyruvic acid 
(6R)-5,10-methylenetetrahydrofolate(2-) +  
(6R)-5,10-methylenetetrahydrofolic acid +  
(6S)-5,6,7,8-tetrahydrofolate(2-) 
(6S)-5,6,7,8-tetrahydrofolic acid 
(R)-3,4-dihydroxy-2-oxobutanoic acid 
(R)-3-(5-benzyloxyindol-3-yl)lactic acid 
(R)-3-hydroxy-2-oxo-4-phosphonooxybutanoic acid 
(R)-indole-3-lactic acid 
(R)-lipoate 
(R)-lipoic acid +   
(S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propionic acid 
(S)-2-chloropropanoic acid 
(S)-3,4-dihydroxy-2-oxobutanoic acid 
(S)-3-fluorolactic acid 
(S)-3-hydroxy-2-oxo-3-phenylpropanoic acid 
(S)-methylmalonaldehydic acid 
1,4-benzoquinone +   
1,4-butanediammonium +  
1-palmitoyl-2-propionyl-sn-glycero-3-phosphocholine 
2'-deoxyadenosine 5'-monophosphate +  
2'-deoxyadenosine 5'-monophosphate(2-) +  
2,2'-iminodipropanoic acid +  
2,2-bis(4-hydroxyphenyl)propanoic acid 
2,3-dihydroxy-2-methylpropanoic acid 
2-(4-cyclohexyl-1-naphthyl)propanoic acid +  
2-aminoisobutyric acid +  
2-aminophenylglyoxylic acid 
2-arylpropionic acid +   
2-dehydro-3-deoxy-D-arabinonic acid 
2-dehydro-3-deoxy-L-arabinonic acid 
2-deoxy-D-ribofuranose 1-phosphate +   
2-hydroxy-3-methylbenzylidenepyruvic acid 
2-hydroxy-3-oxopropanoic acid 
2-hydroxy-4-hydroxymethylbenzylidenepyruvic acid 
2-hydroxypropanoic acid +   
2-methyl-2-(4-\{[(\{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl\}carbonyl)amino]methyl\}phenoxy)propanoic acid 
2-methyl-3-oxopropanoic acid +  
2-oxo-3-(5-oxofuran-2-ylidene)propanoic acid 
2-oxo-3-[4-(sulfooxy)phenyl]propanoic acid 
2-oxobut-3-enoic acid 
2-oxobutanoic acid +   
2-oxodecanoic acid 
2-oxododecanoic acid 
2-oxoglutaramic acid +  
2-oxoglutarate(1-) 
2-oxoglutaric acid +  
2-oxohex-4-enoic acid +  
2-oxohexanoic acid 
2-oxononanoic acid 
2-oxooctadecanoic acid 
2-oxooctanoic acid 
2-oxopent-4-enoic acid 
2-oxopenta-3,4-dienoic acid 
2-oxopentanoic acid 
2-oxophytanic acid 
3'-hydroxyechinenone 
3,3-dimethyl-2-oxobutanoic acid 
3,4,5-trimethoxydihydrocinnamic acid 
3,4-dihydro-4-hydroxyphenylpyruvic acid +  
3,4-dihydroxyphenylpyruvic acid 
3,5-dibromo-4-hydroxyphenylpyruvic acid 
3,5-dihydroxyphenylglyoxylic acid 
3,5-dinitro-4-hydroxyphenylpyruvic acid 
3-(1H-imidazol-1-yl)propanoic acid 
3-(1H-indol-3-yl)propanoic acid  
3-(2,3-dihydroxyphenyl)propanoic acid 
3-(2,4-dihydroxy-5-methoxyphenyl)-2-oxopropanoic acid 
3-(2-hydroxyphenyl)propanoic acid 
3-(3,4-dimethoxyphenyl)propanoic acid 
3-(3-hydroxyphenyl)propanoic acid +  
3-(3-methoxy-4-phenylmethoxyphenyl)-2-oxopropanoic acid 
3-(3-sulfooxyphenyl)propanoic acid 
3-(4-aminophenyl)pyruvic acid 
3-(4-hydroxycyclohex-2-en-1-ylidene)pyruvic acid +  
3-(imidazol-4-yl)pyruvic acid 
3-(indol-3-yl)-2-oxobutyric acid +  
3-(indol-3-yl)pyruvic acid 
3-(methylthio)propionic acid +  
3-(trimethylsilyl)propionic acid 
3-[(1R,2S,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl]pyruvic acid 
3-[(4S)-2,5-dioxoimidazolidin-4-yl]propanoic acid 
3-[(5E)-5-\{[5-(4-chlorophenyl)furan-2-yl]methylidene\}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]propanoic acid 
3-[2-(trifluoromethyl)phenyl]propanoic acid +  
3-[3-methoxy-4-(sulfooxy)phenyl]-2-oxopropanoic acid 
3-[4-hydroxy-3-(sulfooxy)phenyl]-2-oxopropanoic acid 
3-\{(2Z)-2-\{[3-(2-carboxyethyl)-5-\{(Z)-[(3E,4S)-3-ethylidene-4-methyl-5-oxopyrrolidin-2-ylidene]methyl\}-4-methyl-1H-pyrrol-2-yl]methylene\}-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-2H-pyrrol-3-yl\}propanoic acid 
3-amino-3-(4-hydroxyphenyl)propanoic acid 
3-aminoalanine +  
3-bromopyruvic acid  
3-dimethylallyl-4-hydroxyphenylpyruvic acid 
3-fluoropyruvic acid 
3-guanidinopropanoic acid  
3-hydroxy-3-methyl-2-oxobutanoic acid 
3-hydroxy-3-methyl-2-oxopentanoic acid +  
3-hydroxyisobutyric acid +  
3-hydroxyphenyl propanoate 
3-hydroxyphenylpyruvic acid 
3-hydroxypropionic acid +   
3-hydroxypyruvic acid  
3-mercapto-2-mercaptomethylpropanoic acid 
3-mercaptopyruvic acid 
3-methyl-2-oxobutanoic acid  
3-methyl-2-oxovaleric acid +   
3-nitropropanoic acid  
3-oxopropanoic acid +  
3-phenylpropionic acid +   
3-phosphoglyceric acid +   
3-phosphonato-D-glycerate(3-) 
3-phosphonopyruvic acid 
3-sulfinylpyruvic acid 
3-sulfopropanoic acid 
4-(2-aminophenyl)-2,4-dioxobutanoic acid 
4-(3-hydroxy-1-benzothiophen-2-yl)-2-oxobut-3-enoic acid +  
4-(hydroxymethylphosphinyl)-2-oxobutyric acid 
4-amino-4-deoxyprephenic acid 
4-hydroxy-2-oxohexanoic acid +  
4-hydroxy-2-oxopentanoic acid +  
4-hydroxyphenylpyruvic acid +  
4-methyl-2-oxopentanoic acid  
5,6,7,8-tetrahydropteridine 
5-amino-2-oxopentanoic acid 
5-chloro-4-hydroxy-2-oxopentanoic acid 
5-guanidino-2-oxopentanoic acid 
5-guanidino-3-methyl-2-oxopentanoic acid 
5-hydroxybenzimidazolylcob(I)amide 
5-hydroxybenzimidazolylcob(I)amide(1-) 
6,7-dimethyl-8-(1-D-ribityl)lumazine 
6,7-dimethyl-8-(1-D-ribityl)lumazine(1-) 
6-acetamido-2-oxohexanoic acid 
6-amino-2-oxohexanoic acid +  
6-decylubiquinone  
6-hydroxy-2-oxohexanoic acid 
6-hydroxy-FAD 
6-hydroxy-FAD(3-) 
6-phospho-D-gluconic acid 
6-phosphonatooxy-D-gluconate 
aceneuramic acid  
acetyl-CoA +   
adenosine +   
adenosine 5'-monophosphate +   
adenosine 5'-monophosphate(1+) 
adenosine 5'-monophosphate(2-) +  
ADP +   
ADP(3-) +  
alanine +   
aldehydo-D-ribose 5-phosphate(2-) 
alpha-D-glucose 1-phosphate(2-) 
alpha-D-glucose 6-phosphate(2-) 
alpha-D-mannose 6-phosphate(2-) 
alpha-L-galactose 1-phosphate(2-) 
ammonium +   
arabinose +  
arginine +   
aspartate(1-) +  
aspartate(2-) +  
aspartic acid +   
ATP +   
ATP(3-) 
ATP(4-) +  
bacillithiol 
barium(2+) 
benoxaprofen  
beta-(methylenecyclopropyl)pyruvic acid 
beta-alaninate 
beta-alanine +   
beta-alanopine +  
beta-carotene +   
beta-D-fructofuranose 6-phosphate(2-) 
beta-D-glucose 1-phosphate(2-) 
beta-D-glucose 6-phosphate(2-) +  
beta-L-galactose 1-phosphate(2-) 
bezafibrate  
biotin +   
biotinate +  
bis(molybdopterin)tungsten cofactor 
cadmium(2+) +   
calcium(2+) +   
cerium(3+) 
chloride +   
chlorophyll a +  
chlorophyll a(1-) +  
chlorophyll b 
chlorophyll b(1-) 
cis-4-(1-hydroxy-2-naphthyl)-2-oxobut-3-enoic acid 
cis-aconitic acid 
citrate(1-) +  
citrate(2-) +  
citrate(3-) +   
citric acid +   
clobetasol propionate 
cob(I)alamin 
cob(I)alamin(1-) 
cob(II)alamin 
cobalamin +  
cobalt(2+) +   
cobalt(3+) 
cobamamide +   
coenzyme +   
coenzyme F430 
coenzyme F430(5-) 
copper cation +   
copper(1+) +   
copper(2+) +   
corrin 
corrinoid +   
cysteine +   
D-aspartate(1-) +  
D-cysteinate(1-) 
D-cysteinate(2-) 
D-cysteinium 
D-cysteinyl radical +  
D-erythro-isocitrate(3-) 
D-fructofuranose 1,6-bisphosphate(4-) +  
D-fructofuranose 1-phosphate(2-) +  
D-fructofuranose 6-phosphate(2-) 
D-fructose 1,6-bisphosphate +   
D-fructose 6-phosphate +  
D-galactopyranose 1-phosphate +   
D-glucopyranose 1-phosphate +   
D-glucopyranose 1-phosphate(2-) 
D-glucose 6-phosphate +   
D-mannopyranose 6-phosphate(2-) 
D-mannose 1-phosphate +  
D-mannose 6-phosphate +   
D-ribose +   
D-ribose 5-phosphate +   
D-ribulose 5-phosphate(2-) 
D-threo-isocitrate(3-) 
decylplastoquinone 
dehydro-D-arabinono-1,4-lactone 
dGDP 
dihydroferulic acid +  
dihydrogenvanadate 
dihydrolipoamide +   
dihydrourocanic acid 
Dimethoxycinnamic acid 
dipyrromethane cofactor 
dipyrromethane cofactor(4-) 
divinyl chlorophyll a 
divinyl chlorophyll a(1-) 
divinyl chlorophyll b 
divinyl chlorophyll b(1-) 
dTMP +   
echinenone +  
egonolpropanoate 
FAD  
FAD(3-) 
Fe-coproporphyrin III 
Fe-coproporphyrin III(4-) 
Fe4S2O2 iron-sulfur-oxygen cluster 
ferriheme a 
ferriheme a(1-) 
ferroheme b +   
ferroheme b(2-) 
ferroheme c 
ferroheme c(2-) 
flavin adenine dinucleotide +   
flavin mononucleotide +   
flunoxaprofen 
flurbiprofen +   
FMN +   
FMN(3-) +  
FMNH2 +  
FMNH2(2-) 
fructose +   
fructose 1-phosphate +  
fumarate(1-) +  
fumaric acid +   
galactose +   
glucose +   
glutamate(1-) +   
glutamate(2-) +  
glutamic acid +   
glutamine +   
glutathionate(1-) +  
glutathione +   
glyceraldehyde +   
glycerate +  
glyceric acid +   
glycinate +   
glycine +   
glycine betaine +   
glycine betaine hydrate 
glycinium +  
glycolaldehyde +   
glycyl radical +  
glyoxylic acid +   
guanosine +   
heme d cis-diol +  
heme d cis-diol(2-) 
heme o +  
homocysteinate +  
homocysteine +   
hydrogen peroxide +   
hydrogencarbonate +   
hydrogenphosphate +  
hydroquinone +   
Hydroxyphenylpyruvic acid 
hypoxanthine +   
ibuprofen +   
IDP  
indoprofen  
iron cation +   
iron(2+) +   
iron(3+) +   
iron-sulfur-iron cofactor 
iron-sulfur-molybdenum cofactor 
iron-sulfur-vanadium cofactor 
isocitric acid +  
Isopropyl propionate 
keto-phenylpyruvic acid +   
ketoprofen  
L-alaninate +  
L-alanine +   
L-alaninium +  
L-ascorbate +  
L-ascorbic acid +   
L-aspartate(1-) +  
L-aspartate(2-) +  
L-cysteinate(1-) +  
L-cysteinate(2-) 
L-cysteinium +  
L-cysteinyl radical +  
L-erythro-isocitrate(3-) 
L-galactose 1-phosphate +  
L-galactose 1-phosphate(2-) +  
L-homocysteine zwitterion +  
L-mimosine  
L-ribulose 5-phosphate(2-) 
L-threo-isocitrate(3-) 
L-tyrosinate(1-) 
L-tyrosinate(2-) +  
L-tyrosine +   
L-tyrosinium +  
L-xylulose 5-phosphate(2-) 
lanthanum(3+) 
lead(2+) +   
lignin cw compound-2040 
lignin cw compound-2041 
lignin cw compound-2042 
lignin cw compound-3052 
lignin cw compound-3056 
lipoate +  
lipoic acid +   
Loniphenyruviridoside B, (rel)- 
Loniphenyruviridoside C 
loxoprofen +   
magnesium(2+) +  
malate(2-) +  
malic acid +   
manganese(2+) +   
mannose +   
menaquinone-7  
mercaptopropanoic acid +   
meta-hydroxyphenylhydracrylic acid 
Methyl 3-(4-methoxyphenyl)-2-oxopropanoate 
methylcobalamin  
miroprofen 
molybdopterin cofactor +  
mycothiol +  
myo-inositol hexakisphosphate  
myo-inositol hexakisphosphate(12-) 
N(3)-oxalyl-L-2,3-diaminopropionic acid 
N(6)-(1,2-dicarboxyethyl)-AMP 
N,N,N-trimethylglycinium +  
N-(2-hydroxyethyl)iminodiacetic acid 
N-carbamoyl-beta-alanine 
N-methyl-2-oxoglutaramic acid 
N-propanoyl-L-methionine 
NAD +   
NAD(+)  
NAD(1-) +  
NADH +  
NADH(2-) +  
NADP zwitterion +   
NADP(+) +   
NADP(3-) 
NADPH +  
NADPH(4-) +  
Ni(II)-pyridinium-3,5-bisthiocarboxylate mononucleotide(1-) 
Ni(II)-pyridinium-3,5-bisthiocarboxylic acid mononucleotide 
nickel cation +   
nickel(2+) +   
nicotinamide +   
NiFe4S4 cluster 
NiFe4S5 cluster 
O-propanoylcarnitine +  
omega-(methylthio)-2-oxocarboxylic acid +   
oxalatosuccinate(3-) +  
oxalosuccinic acid +  
oxaluric acid 
oxaprozin  
pantetheine 4'-phosphate +  
pantetheine 4'-phosphate(2-) +  
pantothenic acids +   
perquinoline B 
phenylglyoxylic acid +   
phloretic acid +   
phosphoenolpyruvate  
phosphoenolpyruvic acid 
phosphonatoenolpyruvate 
phylloquinone  
phytochromobilin +  
polypeptide-derived cofactor +  
porphyrins +   
potassium(1+) +   
premycofactocin +  
prenyl-FMN 
prenyl-FMN(2-) 
prenyl-FMNH2 
propanoate ester +   
propanoyl phosphate 
propanoyl-AMP 
propanoyl-AMP(1-) 
propanoyl-CoAs +  
propionamide +   
propionyl group +  
propionyl-CoA +   
propionylglycine 
prosthetic group +   
pseudouridine +  
purine +   
putrescine +   
pyridoxal +   
pyridoxal 5'-phosphate +   
pyridoxal 5'-phosphate(2-) 
pyridoxal hydrochloride 
pyridoxine +   
pyrroloquinoline cofactor +   
pyrroloquinoline quinone  
pyrroloquinoline quinone(3-) 
pyruvate +  
pyruvic acid +   
A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.
riboflavin +   
riboflavin(1-) +  
ribulose 5-phosphate +  
S-adenosyl-L-homocysteinate 
S-adenosyl-L-homocysteine  
S-adenosyl-L-methionine +   
S-adenosyl-L-methionine zwitterion +  
sapropterin +   
Schizotenuin F 
serinate +  
serine +   
serinium +  
siderophore +   
siroheme 
siroheme(8-) 
sirohydrochlorin +  
sirohydrochlorin(8-) 
sodium(1+) +   
spermidine +   
spermidine(3+) +  
spermine +   
spermine(4+) +  
strontium(2+) 
succinate(1-) 
succinic acid +   
sulfate +   
tetra-mu3-sulfido-tetrairon +  
tetrahydro-4-hydroxyphenylpyruvic acid +  
tetrahydromonapterin 
thiamine(1+) diphosphate +  
thiamine(1+) diphosphate(3-) 
trans-aconitate(3-) 
trans-aconitic acid 
tropic acid +   
tyrosine +   
UDP-alpha-D-glucose  
UDP-alpha-D-xylose 
uridine +   
vanadium cation +  
Vanillactic acid 
Vanilpyruvic acid 
vitamin B6 phosphate +   
xanthine +   
xylulose 5-phosphate +   
zeaxanthin +  
zinc(2+) +   

Synonyms
Related Synonyms: 2-Oxopropanoic acid ;   2-Oxopropansaeure ;   2-Oxopropionsaeure ;   2-ketopropionic acid ;   BTS ;   Brenztraubensaeure ;   CH3COCOOH ;   Formula=C3H4O3 ;   InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6) ;   InChIKey=LCTONWCANYUPML-UHFFFAOYSA-N ;   Pyroracemic acid ;   SMILES=CC(=O)C(O)=O ;   acetylformic acid ;   acide pyruvique ;   alpha-Oxopropionsaeure ;   alpha-ketopropionic acid
Alternate IDs: CHEBI:26466 ;   CHEBI:45253 ;   CHEBI:8685
Xrefs: Beilstein:506211 ;   CAS:127-17-3 ;   DrugBank:DB00119 ;   ECMDB:ECMDB00243 ;   Gmelin:101087 ;   HMDB:HMDB0000243 ;   KEGG:C00022 ;   KNApSAcK:C00001200 ;   LIPID_MAPS_instance:LMFA01060077
Xref Mesh: MESH:D019289
Xrefs: MetaCyc:PYRUVATE ;   PDBeChem:PYR ;   PMID:11762589 ;   PMID:19260671 ;   PMID:22150460 ;   PMID:22233273 ;   PMID:22735334 ;   PMID:22770225 ;   Reaxys:506211 ;   Wikipedia:Pyruvic_acid ;   YMDB:YMDB00175
Cyclic Relationships: is_conjugate_acid_of CHEBI:15361

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