Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2059)
Drug Name
Oxoglutarate
Synonyms
Alphaketoglutaric acid; Bis(L-arginin)-2-oxoglutarat; Glutaric acid, 2-oxo-; Glutaric acid, alpha keto; 2-Oxoglutarate; Oxoglutaric acid; Pentanedioic acid, 2-oxo-; Pentanedioic acid, oxo-; alpha Ketoglutarate; alpha ketoglutaric acid; alpha-Ketoglutaric acid alpha; alpha-Oxoglutaric acid; alpha-ketoglutarate; alpha-ketoglutaric acid; 2-Oxo-1,5-pentanedioic acid; 2-Oxo-Glutaric Acid; 2-Oxopentanedioic acid; 2-ketoglutarate; 2-ketoglutaric acid; 2-oxoglutarate; 2-oxoglutaric acid; 328-50-7; AI3-26938; MFCD00004165; NSC 17391
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 146.1 Topological Polar Surface Area 91.7
Heavy Atom Count 10 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
51
PubChem SID
3328 ; 80706 ; 820888 ; 820890 ; 820952 ; 821199 ; 821363 ; 821365 ; 826540 ; 827040 ; 828687 ; 828688 ; 828690 ; 836159 ; 837490 ; 837495 ; 837496 ; 837918 ; 841741 ; 3133601 ; 4252672 ; 6312360 ; 7885202 ; 7885817 ; 8026183 ; 8138018 ; 8145356 ; 8150433 ; 10319709 ; 10322722 ; 10518773 ; 11405806 ; 11459129 ; 11459622 ; 11532715 ; 14710598 ; 14710663 ; 14716068 ; 14716122 ; 15321557 ; 17389187 ; 17424980 ; 22390397 ; 24438432 ; 24698269 ; 24844201 ; 24844229 ; 24875185 ; 24896202 ; 24896211
ChEBI ID
CHEBI:30915
CAS Number
328-50-7
TTD Drug ID
D09KQZ
Formula
C5H6O5
Canonical SMILES
C(CC(=O)O)C(=O)C(=O)O
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Acetyl Coenzyme A DM003095
444493
Unclear 1 [3]
Glutamate DM000317
33032
Unclear 1 [3]
Oxoglutarate Metabolite C2 DM004081 N. A. Oxidation - Oxidationn 1 [5]
Amino acid DM002455 N. A. Unclear 2 [3]
L-Glutamine DM001343
5961
Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004452 Oxoglutarate Glutamate Unclear gltB ... [3]
MR004455 Oxoglutarate Acetyl-CoA Unclear Unclear [3]
MR004456 Oxoglutarate Oxoglutarate Metabolite C2 Oxidation - Oxidationn hE1a [5]
MR004453 Glutamate Glutamine Unclear GS [3]
MR004454 Glutamate Amino acid Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Factor inhibiting HIF-1 (HIF1AN) DME0506 Homo sapiens
HIF1N_HUMAN
1.14.11.3
[2]
Glutamate synthase [NADPH] large chain (gltB) DMEN202 Escherichia coli
GLTB_ECOLI
1.4.1.13
[3]
glutamine synthetase (GS) DMEN204 Escherichia coli Not Available Not Available [3]
HIF-prolyl hydroxylase 2 (EGLN1) DME0462 Homo sapiens
EGLN1_HUMAN
1.14.11.29
[4]
HIF-prolyl hydroxylase 3 (EGLN3) DME0507 Homo sapiens
EGLN3_HUMAN
1.14.11.29
[4]
human thiamin diphosphate (ThDP)-dependent enzyme 2-oxoadipate dehydrogenase (hE1a) DMEN205 Homo sapiens Not Available Not Available [5]
NADP-specific glutamate dehydrogenase (gdhA) DMEN203 Escherichia coli
DHE4_ECOLI
1.4.1.4
[3]
Prolyl 3-hydroxylase 1 (P3H1) DME0508 Homo sapiens
P3H1_HUMAN
1.14.11.7
[6]
Prolyl 3-hydroxylase 2 (P3H2) DME0509 Homo sapiens
P3H2_HUMAN
1.14.11.7
[6]
Prolyl 4-hydroxylase alpha-1 (P4HA1) DME0461 Homo sapiens
P4HA1_HUMAN
1.14.11.2
[7]
Prolyl 4-hydroxylase alpha-2 (P4HA2) DME0460 Homo sapiens
P4HA2_HUMAN
1.14.11.2
[7]
Prolyl 4-hydroxylase alpha-3 (P4HA3) DME0463 Homo sapiens
P4HA3_HUMAN
1.14.11.2
[8]
⏷ Show the Full List of 12  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
HIF-prolyl hydroxylase 2 (EGLN1) DME0462 Km = 0.02 microM
EGLN1_HUMAN
[4]
HIF-prolyl hydroxylase 3 (EGLN3) DME0507 Km = 0.055 microM
EGLN3_HUMAN
[4]
Factor inhibiting HIF-1 (HIF1AN) DME0506 Km = 0.02 microM
HIF1N_HUMAN
[2]
Prolyl 3-hydroxylase 1 (P3H1) DME0508 Km = 0.08 microM
P3H1_HUMAN
[6]
Prolyl 3-hydroxylase 2 (P3H2) DME0509 Km = 0.08 microM
P3H2_HUMAN
[6]
Prolyl 4-hydroxylase alpha-1 (P4HA1) DME0461 Km = 0.022 microM
P4HA1_HUMAN
[7]
Prolyl 4-hydroxylase alpha-2 (P4HA2) DME0460 Km = 0.022 microM
P4HA2_HUMAN
[7]
Prolyl 4-hydroxylase alpha-3 (P4HA3) DME0463 Km = 0.06 microM
P4HA3_HUMAN
[8]
⏷ Show the Full List of 8  DME(s)
References
1 The IUPHAR/BPS Guide to PHARMACOLOGY in 2020: extending immunopharmacology content and introducing the IUPHAR/MMV Guide to MALARIA PHARMACOLOGY. Nucleic Acids Res. 2020 Jan 8;48(D1):D1006-D1021. (Ligand id: 3636).
2 The facial triad in the alpha-ketoglutarate dependent oxygenase FIH: a role for sterics in linking substrate binding to O2 activation. J Inorg Biochem. 2017 Jan;166:26-33.
3 The Emergence of 2-Oxoglutarate as a Master Regulator Metabolite
4 Characterization of the human prolyl 4-hydroxylases that modify the hypoxia-inducible factor. J Biol Chem. 2003 Aug 15;278(33):30772-80.
5 The mitochondrial 2-oxoadipate and 2-oxoglutarate dehydrogenase complexes share their E2 and E3 components for their function and both generate reactive oxygen species
6 Characterization of recombinant human prolyl 3-hydroxylase isoenzyme 2, an enzyme modifying the basement membrane collagen IV. J Biol Chem. 2008 Jul 11;283(28):19432-9.
7 Prolyl 4-hydroxylases, the key enzymes of collagen biosynthesis. Matrix Biol. 2003 Mar;22(1):15-24.
8 Identification and characterization of a third human, rat, and mouse collagen prolyl 4-hydroxylase isoenzyme. J Biol Chem. 2003 Nov 28;278(48):47685-93.

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