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alpha-ketoglutaric acid

chemical compound
Class type of: fatty acid, biogenic acyclic ketone Q306140

Facts

11 properties
Instance of
type of chemical entity
Subclass of
fatty acid, biogenic acyclic ketone
Part of
oxoglutarate:malate antiporter activity[7]
Canonical SMILES
C(CC(=O)O)C(=O)C(=O)O[5]
Chemical formula
C₅H₆O₅[6]
Found in taxon
Pycnandra acuminata, Chlamydomonas reinhardtii, Phycomyces blakesleeanus, Fasciola hepatica, Streptomyces albus, Homo sapiens, Streptomyces venezuelae, Streptomyces hygroscopicus, Caenorhabditis elegans, Murraya paniculata, Escherichia coli, common sunflower, Humulus lupulus, Spinacia oleracea, Cucurbita, Phaseolus vulgaris, Pisum sativum, Oryza molida, Streptomyces caespitosus, tomato[10][11][12][13][14][15][16][17][18][19][20][21][22][23]
Has part(s)
oxygen, carbon[8][9]
Mass
+146.022[24]
Medical condition treated
kidney failure[26]
Melting point
+115.0[25]
Physically interacts with
Oxoglutarate receptor 1[4]
🏷️ Also known as
en oxoglutarate en oxoglutaric acid en 2-ketoglutarate en 2-ketoglutaric acid en Α-Ketoglutaric acid en α-ketoglutarate en 2-Oxo-1,5-pentanedioic acid en 2-oxoglutaric acid en 2-Oxopentanedioate en 2-Oxo-1,5-pentanedioate en 2-oxopentanedioic acid en 2-oxoglutarate en alpha-ketoglutaric acid ar ألفا-كيتوغلوتارات cs Oxoglutarát cs 2-oxoglutarát cs Kyselina α-ketoglutarátová cs 2-ketoglutarát cs Ketoglutarát cs Α-ketoglutarát
🔖 Identifiers · 39
OpenAlex ID
C2910453370
CAS Registry Number
328-50-7
Cannabis Database ID
006340
ChEBI ID
30915
ChEMBL ID
CHEMBL1686
ChemSpider ID
50
CosIng number
34798
DSSTOX compound identifier
DTXCID3013179
DSSTox substance ID
DTXSID5033179
DrugBank ID
DB08845
EC number
206-330-3
ECHA Substance Infocard ID
100.005.756
Show all 39 identifiers +27
Encyclopædia Britannica Online ID
topic/alpha-oxoglutarate
FL number
08.037
Freebase ID
/m/04f03
Gmelin number
602480
Google Knowledge Graph ID
/g/11jp2r8t5d
Great Russian Encyclopedia portal ID
al-fa-ketoglutarovaia-kislota-854344
Guide to Pharmacology Ligand ID
3636
Human Metabolome Database ID
HMDB0000208
InChI
InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
InChIKey
KPGXRSRHYNQIFN-UHFFFAOYSA-N
JECFA number
634
KEGG ID
C00026
KNApSAcK ID
C00000769
MassBank accession ID
MSBNK-NAIST-KNA00530, MSBNK-NAIST-KNA00531, MSBNK-NAIST-KNA00533, MSBNK-NAIST-KNA00700, MSBNK-NAIST-KNA00701, MSBNK-NAIST-KNA00702, MSBNK-Osaka_Univ-OUF00113, MSBNK-RIKEN-PR010210, MSBNK-Kazusa-KZ000080, MSBNK-Keio_Univ-KO001528, MSBNK-Keio_Univ-KO001529, MSBNK-Keio_Univ-KO001530, MSBNK-Keio_Univ-KO001531
Microsoft Academic ID (discontinued)
2776215227
NMRShiftDB structure ID
30095876
NSC number
17391
PDB ligand ID
AKG
Probes And Drugs ID
PD014389
PubChem CID
51, 156274072
Reaxys registry number
1705689
RxNorm CUI
17511
SPLASH
splash10-0002-0900000000-c3c62f83bff99f44f7ab, splash10-0zfr-6900000000-b6d8379db3e3f1480b14, splash10-0a4i-9300000000-4fde39bb93cde5a27f23, splash10-00i0-9000000000-4343832f3a55842423a9, splash10-0002-0925200000-37db185093f01ca47a55, splash10-0a4i-9000000000-6e43f767847790112b65, splash10-0udi-0900000000-1367eeeb6ad64c67a0aa, splash10-000t-0915051100-f82c99c58327e411a2bc, splash10-0a4i-9000000000-4f842c3673925d29c402, splash10-0udi-0900000000-5e751351656f6eb62de3, splash10-0002-1910000000-3277227b9c4da4baa1f7, splash10-00di-9300000000-974bce546caa4fbe6b0f, splash10-0002-0900000000-ac1341c26718f471f281, splash10-000b-2900000000-e514f7afea2490bbe9ed, splash10-0zfr-6900000000-7fc343a243ce5d2a4f39, splash10-052s-4920000000-bf7ed92c68fd4c8dbb6b, splash10-000i-9710000000-d0aea11e947b042571f9, splash10-0fba-9200000000-4e367c66e94c51eb1a1b, splash10-0a4l-9800000000-30495b2afdd3526854e7, splash10-0a4i-9200000000-1a7af9946604baa8b3d2
SureChEMBL ID
23244722, 7400
UM-BBD compound ID
c0880
UNII
8ID597Z82X
UniChem compound ID
72549

Report an error or request removal Lineage (PROV-JSON)

🔗 Connections
Found in taxon 17
tomato, Pisum sativum, Spinacia oleracea, common sunflower, Phaseolus vulgaris, Escherichia coli, Oryza molida, Humulus lupulus +9 more
Has part(s) 2
oxygen, carbon
Belongs to 1
arginine alphaketoglutarate
Medical condition treated 1
kidney failure
Subclass of 1
fatty acid
← Drug or therapy used for treatment 1
kidney failure
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Summary

alpha-ketoglutaric acid is a type of chemical entity[1]. It is a type of fatty acid[2] and biogenic acyclic ketone[3].

References

Programmatic citations — every numbered marker resolves to a verifiable graph row below.

Direct Wikidata claims

  1. [4] ↑ . IUPHAR/BPS Guide to PHARMACOLOGY. Retrieved . wikidata.org.
  2. [5] ↑ . PubChem. Retrieved . wikidata.org.
  3. [6] ↑ . PubChem. Retrieved . wikidata.org.
  4. [2] ↑ . wikidata.org.
  5. [3] ↑ . wikidata.org.
  6. [7] ↑ . Gene Ontology release 2020-05-02. wikidata.org.
  7. [8] ↑ . wikidata.org.
  8. [9] ↑ . wikidata.org.
  9. [10] ↑ . LC–MS and GC–MS metabolite profiling of nickel(II) complexes in the latex of the nickel-hyperaccumulating tree Sebertia acuminata and identification of methylated aldaric acid as a new nickel(II) ligand. wikidata.org.
  10. [11] ↑ . The response of Chlamydomonas reinhardtii to nitrogen deprivation: a systems biology analysis. wikidata.org.
  11. [12] ↑ . Acidic metabolites from Phycomyces blakesleeanus. wikidata.org.
  12. [13] ↑ . Some Acids Belonging to the Citric Acid Cycle in the Liver Fluke, Fasciola hepatica, L.. wikidata.org.
  13. [14] ↑ . Über die Bildung von DL-Alanin in Kulturen einer Mutante vonStreptomyces albus var. metamycinusJA 3626. wikidata.org.
  14. [15] ↑ . Recon 2.2: from reconstruction to model of human metabolism. wikidata.org.
  15. [16] ↑ . Excretion of alpha-keto acids by strains of Streptomyces venezuelae. wikidata.org.
  16. [17] ↑ . Induzierbare Akkumulation von α-Ketoglutarsäure in Kulturen eines Makrolidantibioticum-bildenden Stammes vonStreptomyces hygroscopicus JA 6599. wikidata.org.
  17. [18] ↑ . Modeling Meets Metabolomics-The WormJam Consensus Model as Basis for Metabolic Studies in the Model Organism. wikidata.org.
  18. [19] ↑ . Metabolomic comparative analysis of the phloem sap of curry leaf tree (Bergera koenegii), orange jasmine (Murraya paniculata), and Valencia sweet orange (Citrus sinensis) supports their differential responses to Huanglongbing.. wikidata.org.
  19. [20] ↑ . Investigation on response of the metabolites in tricarboxylic acid cycle of Escherichi coli and Pseudomonas aeruginosa to antibiotic perturbation by capillary electrophoresis. wikidata.org.
  20. [21] ↑ . Metabolic profiles of sunflower genotypes with contrasting response to Sclerotinia sclerotiorum infection. wikidata.org.
  21. [22] ↑ . Transcriptome analysis of bitter acid biosynthesis and precursor pathways in hop (Humulus lupulus).. wikidata.org.
  22. [23] ↑ . Differences in the metabolite profiles of spinach (Spinacia oleracea L.) leaf in different concentrations of nitrate in the culture solution. wikidata.org.
  23. [24] ↑ . PubChem. Retrieved . wikidata.org.
  24. [25] ↑ . Jean-Claude Bradley Open Melting Point Dataset. wikidata.org.
  25. [26] ↑ . Inxight: Drugs Database. Retrieved . drugs.ncats.io. Provenance: wikidata.org.

Class ancestry

  1. [1] ↑ . Wikidata. wikidata.org.

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Edit History

Rolling log of changes to this entity's Wikidata record. Values shown reflect the current state of each edited property — follow the history link to see the precise diff for any edit.

  1. 20w ago · Nabbegat · 2026-06-19 view diff on Wikidata ↗
    Has parts → —
    Instance of → type of chemical entity
    Part of → —
    Medical condition treated → kidney failure
    + 10 other properties edited (see Wikidata diff for full list)
    "/* wbeditentity-update-languages-short:0||tr */ QuickStatements 3.0 [[:toollabs:qs-dev/batch/37300|batch #37300]]"
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