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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:pyruvic acid
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Accession:CHEBI:32816 term browser browse the term
Definition:A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.
Synonyms:related_synonym: 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
 alt_id: CHEBI:26466;   CHEBI:45253;   CHEBI:8685
 xref: 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
 xref: MetaCyc:PYRUVATE;   PDBeChem:PYR;   PMID:11762589;   PMID:19260671;   PMID:22150460;   PMID:22233273;   PMID:22735334;   PMID:22770225;   Reaxys:506211;   Wikipedia:Pyruvic_acid;   YMDB:YMDB00175
 cyclic_relationship: is_conjugate_acid_of CHEBI:15361



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pyruvic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Acaca acetyl-CoA carboxylase alpha multiple interactions ISO [Pyruvic Acid co-treated with Glucose] results in increased phosphorylation of ACACA protein CTD PMID:19071085 NCBI chr10:69,014,261...69,276,453
Ensembl chr10:69,014,170...69,276,457
JBrowse link
G Adrb3 adrenoceptor beta 3 multiple interactions ISO [BRL 37344 binds to and results in increased activity of ADRB3 protein] which results in increased abundance of Pyruvic Acid CTD PMID:20930473 NCBI chr16:64,839,820...64,844,552
Ensembl chr16:64,841,788...64,844,552
JBrowse link
G Atp5f1a ATP synthase F1 subunit alpha multiple interactions EXP [Glucose deficiency co-treated with Galactose co-treated with Pyruvic Acid] results in increased expression of ATP5F1A protein CTD PMID:25997894 NCBI chr18:71,292,406...71,300,342
Ensembl chr18:71,292,374...71,300,794
JBrowse link
G Becn1 beclin 1 multiple interactions EXP [Glucose deficiency co-treated with Galactose co-treated with Pyruvic Acid] inhibits the reaction [Doxorubicin results in decreased expression of BECN1 protein] CTD PMID:25997894 NCBI chr10:86,231,387...86,246,742
Ensembl chr10:86,231,388...86,246,742
JBrowse link
G Casp3 caspase 3 multiple interactions EXP [Glucose deficiency co-treated with Galactose co-treated with Pyruvic Acid] inhibits the reaction [Doxorubicin results in increased activity of CASP3 protein] CTD PMID:25997894 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp9 caspase 9 multiple interactions EXP [Glucose deficiency co-treated with Galactose co-treated with Pyruvic Acid] inhibits the reaction [Doxorubicin results in increased activity of CASP9 protein] CTD PMID:25997894 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Ctbp1 C-terminal binding protein 1 affects localization
multiple interactions
ISO Pyruvic Acid affects the localization of CTBP1 protein
Pyruvic Acid inhibits the reaction [CTBP1 protein binds to CTBP2 protein]; Pyruvic Acid inhibits the reaction [CTBP1 protein binds to NR5A1 protein]; Pyruvic Acid promotes the reaction [CTBP1 protein binds to CYP17A1 promoter]
CTD PMID:18184656 NCBI chr14:77,455,580...77,482,821
Ensembl chr14:77,455,696...77,482,821
JBrowse link
G Ctbp2 C-terminal binding protein 2 affects localization
multiple interactions
ISO Pyruvic Acid affects the localization of CTBP2 protein
Pyruvic Acid inhibits the reaction [CTBP1 protein binds to CTBP2 protein]; Pyruvic Acid promotes the reaction [CTBP2 protein binds to CYP17A1 promoter]
CTD PMID:18184656 NCBI chr 1:187,782,064...187,918,115
Ensembl chr 1:187,782,682...187,920,222
JBrowse link
G Cyp17a1 cytochrome P450, family 17, subfamily a, polypeptide 1 multiple interactions
increases expression
ISO Pyruvic Acid promotes the reaction [CTBP1 protein binds to CYP17A1 promoter]; Pyruvic Acid promotes the reaction [CTBP2 protein binds to CYP17A1 promoter]; Pyruvic Acid promotes the reaction [NR5A1 protein binds to CYP17A1 promoter]
Pyruvic Acid results in increased expression of CYP17A1 mRNA
CTD PMID:18184656 NCBI chr 1:245,535,462...245,543,148
Ensembl chr 1:245,535,462...245,541,573
JBrowse link
G Dek DEK proto-oncogene multiple interactions ISO DEK protein results in decreased chemical synthesis of and results in decreased secretion of Pyruvic Acid CTD PMID:28558019 NCBI chr17:17,580,804...17,602,825
Ensembl chr17:17,580,843...17,602,808
JBrowse link
G Faslg Fas ligand multiple interactions ISO Pyruvic Acid inhibits the reaction [FASL protein results in increased chemical synthesis of Hydrogen Peroxide] CTD PMID:17724027 NCBI chr13:74,151,519...74,172,760
Ensembl chr13:74,154,954...74,162,215
JBrowse link
G Gcg glucagon multiple interactions
increases secretion
EXP 1-Methyl-3-isobutylxanthine promotes the reaction [Pyruvic Acid results in increased secretion of GCG protein]; Calcium affects the reaction [Pyruvic Acid results in increased secretion of GCG protein]; Colforsin promotes the reaction [Pyruvic Acid results in increased secretion of GCG protein]; INS protein inhibits the reaction [Pyruvic Acid results in increased secretion of GCG protein]; Zinc inhibits the reaction [Pyruvic Acid results in increased secretion of GCG protein] CTD PMID:15919803 NCBI chr 3:47,113,914...47,122,929
Ensembl chr 3:47,113,914...47,122,929
JBrowse link
G Idh2 isocitrate dehydrogenase (NADP(+)) 2 increases abundance
multiple interactions
ISO IDH2 protein mutant form results in increased abundance of Pyruvic Acid
Triazines inhibits the reaction [IDH2 protein mutant form results in increased abundance of Pyruvic Acid]
CTD PMID:27469509 NCBI chr 1:134,038,644...134,057,969
Ensembl chr 1:134,029,772...134,058,025
JBrowse link
G Il4 interleukin 4 multiple interactions EXP Pyruvic Acid inhibits the reaction [Mercuric Chloride results in increased expression of IL4 mRNA] CTD PMID:11222498 NCBI chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750
JBrowse link
G Ins2 insulin 2 multiple interactions EXP INS protein inhibits the reaction [Pyruvic Acid results in increased secretion of GCG protein] CTD PMID:15919803 NCBI chr 1:197,843,277...197,992,522
Ensembl chr 1:197,843,281...197,864,775
JBrowse link
G Kcnh2 potassium voltage-gated channel subfamily H member 2 multiple interactions ISO Pyruvic Acid inhibits the reaction [[Deoxyglucose co-treated with Glucose deficiency] results in decreased activity of KCNH2 protein] CTD PMID:12531891 NCBI chr 4:10,826,834...10,859,009
Ensembl chr 4:10,826,928...10,859,008
JBrowse link
G Lep leptin increases secretion
multiple interactions
EXP Pyruvic Acid results in increased secretion of LEP protein
INS1 protein promotes the reaction [Pyruvic Acid results in increased secretion of LEP protein]
CTD PMID:10780946 NCBI chr 4:57,661,127...57,675,262
Ensembl chr 4:57,661,131...57,675,262
JBrowse link
G Mt-co1 mitochondrially encoded cytochrome c oxidase I multiple interactions EXP [Glucose deficiency co-treated with Galactose co-treated with Pyruvic Acid] results in increased expression of COX1 protein CTD PMID:25997894 NCBI chr MT:5,323...6,867
Ensembl chr MT:5,323...6,867
JBrowse link
G Ndufb8 NADH:ubiquinone oxidoreductase subunit B8 multiple interactions EXP [Glucose deficiency co-treated with Galactose co-treated with Pyruvic Acid] results in increased expression of NDUFB8 protein CTD PMID:25997894 NCBI chr 1:243,408,659...243,413,701
Ensembl chr 1:243,408,619...243,413,817
JBrowse link
G Nr5a1 nuclear receptor subfamily 5, group A, member 1 multiple interactions ISO Pyruvic Acid inhibits the reaction [CTBP1 protein binds to NR5A1 protein]; Pyruvic Acid promotes the reaction [NR5A1 protein binds to CYP17A1 promoter] CTD PMID:18184656 NCBI chr 3:22,464,786...22,486,328
Ensembl chr 3:22,465,502...22,486,328
JBrowse link
G Pdk4 pyruvate dehydrogenase kinase 4 multiple interactions
affects abundance
ISO [PDK4 affects the abundance of Pyruvic Acid] which results in increased expression of SIRT1 CTD PMID:21182459 NCBI chr 4:33,591,796...33,601,798
Ensembl chr 4:33,589,799...33,601,850
JBrowse link
G Ppargc1a PPARG coactivator 1 alpha multiple interactions ISO Pyruvic Acid inhibits the reaction [PPARGC1A protein promotes the reaction [Pregnenolone Carbonitrile results in increased expression of CYP3A11 mRNA]]; SIRT1 mRNA affects the reaction [Pyruvic Acid inhibits the reaction [PPARGC1A protein promotes the reaction [Pregnenolone Carbonitrile results in increased expression of CYP3A11 mRNA]]]
[Pyruvic Acid co-treated with Glucose] results in decreased acetylation of PPARGC1A protein
CTD PMID:19071085 PMID:21933665 NCBI chr14:58,860,752...59,516,525
Ensembl chr14:58,861,144...59,512,656
JBrowse link
G Sirt1 sirtuin 1 multiple interactions
increases expression
ISO [Glucose deficiency co-treated with Galactose co-treated with Amino Acids co-treated with Pyruvic Acid] inhibits the reaction [resveratrol results in increased expression of SIRT1 protein]; [Pyruvic Acid co-treated with Glucose] results in increased expression of and results in increased activity of SIRT1 protein
Pyruvic Acid results in increased expression of SIRT1 mRNA
[PDK4 affects the abundance of Pyruvic Acid] which results in increased expression of SIRT1; SIRT1 mRNA affects the reaction [Pyruvic Acid inhibits the reaction [PPARGC1A protein promotes the reaction [Pregnenolone Carbonitrile results in increased expression of CYP3A11 mRNA]]]
CTD PMID:19071085 PMID:21182459 PMID:21933665 PMID:27358235 NCBI chr20:25,307,143...25,329,260
Ensembl chr20:25,306,917...25,329,260
JBrowse link
G Slc16a1 solute carrier family 16 member 1 multiple interactions ISO Pyruvic Acid inhibits the reaction [SLC16A1 protein results in increased uptake of Butyrates]; Pyruvic Acid inhibits the reaction [SLC16A1 protein results in increased uptake of Lactic Acid] CTD PMID:15804185 PMID:19023563 NCBI chr 2:192,123,755...192,144,617
Ensembl chr 2:192,124,289...192,144,611
JBrowse link
G Slc2a4 solute carrier family 2 member 4 multiple interactions ISO Pyruvic Acid inhibits the reaction [Palmitates results in decreased expression of SLC2A4 mRNA] CTD PMID:21802492 NCBI chr10:54,666,015...54,671,581
Ensembl chr10:54,666,015...54,671,565
JBrowse link
G Sod1 superoxide dismutase 1 multiple interactions ISO Pyruvic Acid inhibits the reaction [SOD1 protein mutant form promotes the reaction [cupric chloride results in increased abundance of Peroxides]]; Pyruvic Acid inhibits the reaction [SOD1 protein mutant form results in increased susceptibility to cupric chloride] CTD PMID:15812313 NCBI chr11:29,456,673...29,462,249
Ensembl chr11:29,456,558...29,462,249
JBrowse link
G Tfam transcription factor A, mitochondrial multiple interactions EXP [Glucose deficiency co-treated with Galactose co-treated with Pyruvic Acid] results in increased expression of TFAM protein CTD PMID:25997894 NCBI chr20:17,356,243...17,368,293
Ensembl chr20:17,356,197...17,368,292
JBrowse link
G Tp53 tumor protein p53 multiple interactions EXP [Glucose deficiency co-treated with Galactose co-treated with Pyruvic Acid] inhibits the reaction [Doxorubicin results in increased expression of TP53 protein] CTD PMID:25997894 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524
JBrowse link
3-bromopyruvic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Casp3 caspase 3 increases cleavage
increases activity
ISO bromopyruvate results in increased cleavage of CASP3 protein
bromopyruvate results in increased activity of CASP3 protein
CTD PMID:24307199 PMID:28433571 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Gapdh glyceraldehyde-3-phosphate dehydrogenase decreases expression ISO bromopyruvate results in decreased expression of GAPDH mRNA CTD PMID:28433571 NCBI chr 4:157,962,312...157,967,158
Ensembl chr 4:157,962,343...157,966,235
JBrowse link
G Hif1a hypoxia inducible factor 1 subunit alpha decreases expression ISO bromopyruvate results in decreased expression of HIF1A CTD PMID:28433571 NCBI chr 6:92,624,059...92,669,262
Ensembl chr 6:92,624,390...92,669,261
JBrowse link
G Hk1 hexokinase 1 decreases activity EXP bromopyruvate results in decreased activity of HK1 protein CTD PMID:22349057 NCBI chr20:30,230,488...30,332,161
Ensembl chr20:30,230,486...30,332,131
JBrowse link
G Hk2 hexokinase 2 decreases activity
decreases response to substance
decreases expression
ISO bromopyruvate results in decreased activity of HK2 protein
HK2 protein results in decreased susceptibility to bromopyruvate
bromopyruvate results in decreased expression of HK2 mRNA; bromopyruvate results in decreased expression of HK2 protein
CTD PMID:21548882 PMID:28433571 NCBI chr 4:115,234,509...115,283,530
Ensembl chr 4:115,234,509...115,283,530
JBrowse link
G Ldha lactate dehydrogenase A decreases expression ISO bromopyruvate results in decreased expression of LDHA mRNA CTD PMID:28433571 NCBI chr 1:97,371,823...97,381,247
Ensembl chr 1:97,366,021...97,433,472
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
increases phosphorylation
ISO Curcumin inhibits the reaction [bromopyruvate results in increased phosphorylation of MAPK1 protein]; S-ethyl glutathione inhibits the reaction [bromopyruvate results in increased phosphorylation of MAPK1 protein] CTD PMID:24307199 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616
JBrowse link
G Mapk3 mitogen activated protein kinase 3 multiple interactions
increases phosphorylation
ISO Curcumin inhibits the reaction [bromopyruvate results in increased phosphorylation of MAPK3 protein]; S-ethyl glutathione inhibits the reaction [bromopyruvate results in increased phosphorylation of MAPK3 protein] CTD PMID:24307199 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Mcl1 MCL1 apoptosis regulator, BCL2 family member decreases expression ISO bromopyruvate results in decreased expression of MCL1 CTD PMID:28433571 NCBI chr 2:183,219,137...183,235,676
Ensembl chr 2:183,219,220...183,222,303
JBrowse link
G Mtor mechanistic target of rapamycin kinase increases expression ISO bromopyruvate results in increased expression of MTOR protein modified form CTD PMID:24307199 NCBI chr 5:158,884,856...158,994,311
Ensembl chr 5:158,884,804...158,994,311
JBrowse link
G Rps6kb1 ribosomal protein S6 kinase B1 increases expression ISO bromopyruvate results in increased expression of RPS6KB1 protein modified form CTD PMID:24307199 NCBI chr10:71,323,777...71,367,908
Ensembl chr10:71,323,777...71,367,908
JBrowse link
G Sdha succinate dehydrogenase complex flavoprotein subunit A decreases expression ISO bromopyruvate results in decreased expression of SDHA mRNA CTD PMID:28433571 NCBI chr 1:28,935,965...28,960,936
Ensembl chr 1:28,940,164...28,961,535
JBrowse link
G Slc16a1 solute carrier family 16 member 1 multiple interactions ISO SLC16A1 protein results in increased uptake of and results in increased susceptibility to bromopyruvate CTD PMID:23202129 NCBI chr 2:192,123,755...192,144,617
Ensembl chr 2:192,124,289...192,144,611
JBrowse link
G Slc2a1 solute carrier family 2 member 1 multiple interactions
decreases expression
ISO [bromopyruvate results in decreased expression of SLC2A1 protein] which results in decreased uptake of Glucose
bromopyruvate results in decreased expression of SLC2A1 mRNA; bromopyruvate results in decreased expression of SLC2A1 protein
CTD PMID:28433571 NCBI chr 5:132,717,196...132,745,416
Ensembl chr 5:132,717,196...132,745,416
JBrowse link
G Sod1 superoxide dismutase 1 multiple interactions ISO SOD1 protein inhibits the reaction [bromopyruvate promotes the reaction [bis((2-oxindol-3-ylimino)-2-(2-aminoethyl)pyridine-N,N')copper(II) results in increased expression of TP53 protein]]; SOD1 protein results in decreased susceptibility to [bromopyruvate co-treated with bis((2-oxindol-3-ylimino)-2-(2-aminoethyl)pyridine-N,N')copper(II)] CTD PMID:21548882 NCBI chr11:29,456,673...29,462,249
Ensembl chr11:29,456,558...29,462,249
JBrowse link
G Stk11 serine/threonine kinase 11 decreases expression ISO bromopyruvate results in decreased expression of STK11 protein modified form CTD PMID:24307199 NCBI chr 7:9,574,553...9,591,315
Ensembl chr 7:9,575,269...9,591,315
JBrowse link
G Tp53 tumor protein p53 multiple interactions ISO bromopyruvate promotes the reaction [bis((2-oxindol-3-ylimino)-2-(2-aminoethyl)pyridine-N,N')copper(II) results in increased expression of TP53 protein]; SOD1 protein inhibits the reaction [bromopyruvate promotes the reaction [bis((2-oxindol-3-ylimino)-2-(2-aminoethyl)pyridine-N,N')copper(II) results in increased expression of TP53 protein]] CTD PMID:21548882 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524
JBrowse link
3-hydroxypyruvic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Aldh2 aldehyde dehydrogenase 2 family member multiple interactions EXP [Disulfiram results in decreased activity of ALDH2 protein] which results in increased susceptibility to hydroxypyruvic acid CTD PMID:21376711 NCBI chr12:34,949,549...34,982,527 JBrowse link
G Cat catalase decreases response to substance EXP CAT protein results in decreased susceptibility to hydroxypyruvic acid CTD PMID:21376711 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478
JBrowse link
keto-phenylpyruvic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Col2a1 collagen type II alpha 1 chain multiple interactions EXP [COL2A1 protein co-treated with Freund's Adjuvant] results in decreased abundance of phenylpyruvic acid; [geniposide co-treated with phellodendrine co-treated with magnoflorine co-treated with Chlorogenic Acid co-treated with crocin co-treated with Flavonoids co-treated with Berberine Alkaloids] inhibits the reaction [[COL2A1 protein co-treated with Freund's Adjuvant] results in decreased abundance of phenylpyruvic acid]; Dexamethasone inhibits the reaction [[COL2A1 protein co-treated with Freund's Adjuvant] results in decreased abundance of phenylpyruvic acid]; huang-lien-chieh-tu-tang inhibits the reaction [[COL2A1 protein co-treated with Freund's Adjuvant] results in decreased abundance of phenylpyruvic acid] CTD PMID:24709313 NCBI chr 7:129,098,489...129,127,620
Ensembl chr 7:129,098,786...129,127,546
JBrowse link
G Slc22a7 solute carrier family 22 member 7 multiple interactions ISO phenylpyruvic acid promotes the reaction [SLC22A7 protein results in increased export of Orotic Acid] CTD PMID:22981274 NCBI chr 9:14,547,073...14,554,354
Ensembl chr 9:14,547,849...14,553,921
JBrowse link
methyl pyruvate term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akt1 AKT serine/threonine kinase 1 multiple interactions ISO methyl pyruvate inhibits the reaction [AKT1 protein mutant form results in increased susceptibility to Glucose deficiency] CTD PMID:15806154 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
JBrowse link
G Slc2a4 solute carrier family 2 member 4 multiple interactions ISO methyl pyruvate inhibits the reaction [Palmitates results in decreased expression of SLC2A4 mRNA]; methyl pyruvate inhibits the reaction [Palmitates results in decreased expression of SLC2A4 protein] CTD PMID:21802492 NCBI chr10:54,666,015...54,671,581
Ensembl chr10:54,666,015...54,671,565
JBrowse link
pyruvate ester term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Nqo1 NAD(P)H quinone dehydrogenase 1 increases expression EXP Ethyl pyruvate increases expression Nqo1 mRNA in liver RGD PMID:31933629 RGD:25823189 NCBI chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19823
    role 19773
      biological role 19773
        biochemical role 19390
          cofactor 15782
            pyruvic acid 47
              (3,5-diiodo-4-hydroxyphenyl)pyruvic acid 0
              (3E)-3-[(1R,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylidene]pyruvic acid 0
              (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid 0
              (3S)-3-methyl-2-oxo-3-phenylpropanoic acid 0
              (4-bromophenylsulfanyl)pyruvic acid 0
              (S)-3-hydroxy-2-oxo-3-phenylpropanoic acid 0
              2-hydroxy-3-carboxybenzylidenepyruvic acid 0
              2-hydroxy-3-methylbenzylidenepyruvic acid 0
              2-hydroxy-4-hydroxymethylbenzylidenepyruvic acid 0
              2-oxo-3-(5-oxofuran-2-ylidene)propanoic acid 0
              2-oxo-3-[4-(sulfooxy)phenyl]propanoic acid 0
              3,4-dihydro-4-hydroxyphenylpyruvic acid + 0
              3,4-dihydroxyphenylpyruvic acid 0
              3,5,3'-triiodothyropyruvic acid 0
              3,5-dibromo-4-hydroxyphenylpyruvic acid 0
              3,5-dichloro-4-hydroxyphenylpyruvic acid 0
              3,5-dinitro-4-hydroxyphenylpyruvic acid 0
              3-(3-methoxy-4-phenylmethoxyphenyl)-2-oxopropanoic acid 0
              3-(4-aminophenyl)pyruvic acid 0
              3-(4-hydroxycyclohex-2-en-1-ylidene)pyruvic acid + 0
              3-(5-benzyloxyindol-3-yl)pyruvic acid 0
              3-(5-hydroxyindol-3-yl)pyruvic acid 0
              3-(imidazol-1-yl)pyruvic acid 0
              3-(imidazol-4-yl)pyruvic acid 0
              3-(imidazol-5-yl)pyruvic acid 0
              3-(indol-3-yl)pyruvic acid 0
              3-[(1R,2S,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl]pyruvic acid 0
              3-[3-methoxy-4-(sulfooxy)phenyl]-2-oxopropanoic acid 0
              3-[4-hydroxy-3-(sulfooxy)phenyl]-2-oxopropanoic acid 0
              3-[hydroxy(oxido)phosphoranyl]pyruvic acid 0
              3-acylpyruvic acid + 0
              3-bromopyruvic acid 17
              3-dimethylallyl-4-hydroxyphenylpyruvic acid 0
              3-fluoropyruvic acid 0
              3-fumarylpyruvic acid 0
              3-hydroxyphenylpyruvic acid 0
              3-hydroxypyruvic acid 2
              3-mercaptopyruvic acid 0
              3-phosphonooxypyruvic acid 0
              3-phosphonopyruvic acid 0
              3-sulfinylpyruvic acid 0
              3-sulfopyruvic acid 0
              4-hydroxy-3-iodophenylpyruvate 0
              4-hydroxy-3-iodophenylpyruvic acid 0
              4-hydroxyphenylpyruvic acid + 0
              Dimethoxycinnamic acid 0
              Hydroxyphenylpyruvic acid 0
              Loniphenyruviridoside B, (rel)- 0
              Loniphenyruviridoside C 0
              Methyl 3-(4-methoxyphenyl)-2-oxopropanoate 0
              Schizotenuin F 0
              Vanillactic acid 0
              Vanilpyruvic acid 0
              beta-(methylenecyclopropyl)pyruvic acid 0
              keto-phenylpyruvic acid + 2
              lignin cw compound-2040 0
              lignin cw compound-2041 0
              lignin cw compound-2042 0
              lignin cw compound-3052 0
              lignin cw compound-3056 0
              methyl pyruvate 2
              pyruvate ester + 3
              pyruvoyl group 0
              tetrahydro-4-hydroxyphenylpyruvic acid + 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19823
    subatomic particle 19821
      composite particle 19821
        hadron 19821
          baryon 19821
            nucleon 19821
              atomic nucleus 19821
                atom 19821
                  main group element atom 19720
                    p-block element atom 19720
                      carbon group element atom 19643
                        carbon atom 19633
                          organic molecular entity 19633
                            organic group 18739
                              organic divalent group 18730
                                organodiyl group 18730
                                  carbonyl group 18678
                                    carbonyl compound 18678
                                      carboxylic acid 18376
                                        monocarboxylic acid 17639
                                          fatty acid 16011
                                            saturated fatty acid 15987
                                              propionic acid 3689
                                                pyruvic acid 47
                                                  (3,5-diiodo-4-hydroxyphenyl)pyruvic acid 0
                                                  (3E)-3-[(1R,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylidene]pyruvic acid 0
                                                  (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid 0
                                                  (3S)-3-methyl-2-oxo-3-phenylpropanoic acid 0
                                                  (4-bromophenylsulfanyl)pyruvic acid 0
                                                  (S)-3-hydroxy-2-oxo-3-phenylpropanoic acid 0
                                                  2-hydroxy-3-carboxybenzylidenepyruvic acid 0
                                                  2-hydroxy-3-methylbenzylidenepyruvic acid 0
                                                  2-hydroxy-4-hydroxymethylbenzylidenepyruvic acid 0
                                                  2-oxo-3-(5-oxofuran-2-ylidene)propanoic acid 0
                                                  2-oxo-3-[4-(sulfooxy)phenyl]propanoic acid 0
                                                  3,4-dihydro-4-hydroxyphenylpyruvic acid + 0
                                                  3,4-dihydroxyphenylpyruvic acid 0
                                                  3,5,3'-triiodothyropyruvic acid 0
                                                  3,5-dibromo-4-hydroxyphenylpyruvic acid 0
                                                  3,5-dichloro-4-hydroxyphenylpyruvic acid 0
                                                  3,5-dinitro-4-hydroxyphenylpyruvic acid 0
                                                  3-(3-methoxy-4-phenylmethoxyphenyl)-2-oxopropanoic acid 0
                                                  3-(4-aminophenyl)pyruvic acid 0
                                                  3-(4-hydroxycyclohex-2-en-1-ylidene)pyruvic acid + 0
                                                  3-(5-benzyloxyindol-3-yl)pyruvic acid 0
                                                  3-(5-hydroxyindol-3-yl)pyruvic acid 0
                                                  3-(imidazol-1-yl)pyruvic acid 0
                                                  3-(imidazol-4-yl)pyruvic acid 0
                                                  3-(imidazol-5-yl)pyruvic acid 0
                                                  3-(indol-3-yl)pyruvic acid 0
                                                  3-[(1R,2S,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl]pyruvic acid 0
                                                  3-[3-methoxy-4-(sulfooxy)phenyl]-2-oxopropanoic acid 0
                                                  3-[4-hydroxy-3-(sulfooxy)phenyl]-2-oxopropanoic acid 0
                                                  3-[hydroxy(oxido)phosphoranyl]pyruvic acid 0
                                                  3-acylpyruvic acid + 0
                                                  3-bromopyruvic acid 17
                                                  3-dimethylallyl-4-hydroxyphenylpyruvic acid 0
                                                  3-fluoropyruvic acid 0
                                                  3-fumarylpyruvic acid 0
                                                  3-hydroxyphenylpyruvic acid 0
                                                  3-hydroxypyruvic acid 2
                                                  3-mercaptopyruvic acid 0
                                                  3-phosphonooxypyruvic acid 0
                                                  3-phosphonopyruvic acid 0
                                                  3-sulfinylpyruvic acid 0
                                                  3-sulfopyruvic acid 0
                                                  4-hydroxy-3-iodophenylpyruvate 0
                                                  4-hydroxy-3-iodophenylpyruvic acid 0
                                                  4-hydroxyphenylpyruvic acid + 0
                                                  Dimethoxycinnamic acid 0
                                                  Hydroxyphenylpyruvic acid 0
                                                  Loniphenyruviridoside B, (rel)- 0
                                                  Loniphenyruviridoside C 0
                                                  Methyl 3-(4-methoxyphenyl)-2-oxopropanoate 0
                                                  Schizotenuin F 0
                                                  Vanillactic acid 0
                                                  Vanilpyruvic acid 0
                                                  beta-(methylenecyclopropyl)pyruvic acid 0
                                                  keto-phenylpyruvic acid + 2
                                                  lignin cw compound-2040 0
                                                  lignin cw compound-2041 0
                                                  lignin cw compound-2042 0
                                                  lignin cw compound-3052 0
                                                  lignin cw compound-3056 0
                                                  methyl pyruvate 2
                                                  pyruvate ester + 3
                                                  pyruvoyl group 0
                                                  tetrahydro-4-hydroxyphenylpyruvic acid + 0
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