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

General Information of Drug (ID: DR2118)
Drug Name
Oxaloacetate
Synonyms
Butanedioic acid, 2-oxo-; Butanedioic acid, oxo-; KHPXUQMNIQBQEV-UHFFFAOYSA-N; Ketosuccinate; Ketosuccinic acid; Oxalacetic acetic; Oxalacetic acid, 98%; OxalaceticAcid; Oxaloethanoate; Oxaloethanoic acid; Oxobutanedioic acid; Oxosuccinic acid; alpha-Ketosuccinic acid; keto-oxaloacetate; oxalacetate; oxalacetic acid; oxaloacetate; oxaloacetic acid; 2-Ketosuccinic acid; 2-Oxobutanedioic acid; 2-Oxosuccinic acid; 2-oxo-butanedioic acid; 2F399MM81J; 328-42-7; CHEBI:30744; EINECS 206-329-8; MFCD00002592; NSC 77688; OAA; UNII-2F399MM81J
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 132.07 Topological Polar Surface Area 91.7
Heavy Atom Count 9 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
970
PubChem SID
3338 ; 118443 ; 583752 ; 583812 ; 824930 ; 825324 ; 827499 ; 835614 ; 841755 ; 3137159 ; 5571665 ; 8026470 ; 8150895 ; 10518772 ; 14719834 ; 15297251 ; 24398024 ; 24439327 ; 24897993 ; 24898047 ; 24898071 ; 26704029 ; 26704031 ; 26704037 ; 26704039 ; 26708897 ; 26709334 ; 26719105 ; 46394380 ; 48414838 ; 49748376 ; 50066357 ; 50091495 ; 53787483 ; 56437667 ; 57320629 ; 57410637 ; 76402907 ; 81040509 ; 81060164 ; 85088401 ; 85088402 ; 85267089 ; 85291449 ; 87574085 ; 88831403 ; 92298111 ; 104296390 ; 104670273 ; 117609703
ChEBI ID
CHEBI:30744
CAS Number
328-42-7
TTD Drug ID
D0V0AI
Formula
C4H4O5
Canonical SMILES
C(C(=O)C(=O)O)C(=O)O
InChI
1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
InChIKey
KHPXUQMNIQBQEV-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
L-Malate DM003440
222656
Reduction - Reduction 1 [3]
PYR DM000331
107735
Unclear 1 [2]
A-acetolactate DM004068
440878
Other reaction - #NAME? 2 [2]
Acetyl-P DM004070
186
Unclear 2 [2]
Acetate DM003441
175
Unclear 3 [2]
Acetoin DM004069
179
Other reaction - aldB 3 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004433 Oxaloacetate Pyruvate Unclear CitM [2]
MR004438 Oxaloacetate L-malate Reduction - Reduction MDH2 [3]
MR004434 Pyruvate A-acetolactate Other reaction - #NAME? #NAME? [2]
MR004436 Pyruvate Acetyl-P Unclear Unclear [2]
MR004435 A-acetolactate Acetoin Other reaction - aldB aldB [2]
MR004437 Acetyl-P Acetate Unclear Unclear [2]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Alpha-acetolactate decarboxylase (aldB) DMEN201 Lactococcus lactis subsp. lactis
ALDC_LACLA
4.1.1.5
[2]
alpha-acetolactate synthase (-ALS) DMEN200 Lactococcus lactis subsp. lactis bv. diacetylactis Not Available Not Available [2]
CitM (citM) DMEN199 Lactococcus lactis subsp. lactis bv. diacetylactis
Q7X4Z5_LACLL
Not Available [2]
Malate dehydrogenase (MDH2) DMEN108 Homo sapiens
MDHM_HUMAN
1.1.1.37
[3]
Oxaloacetate decarboxylase (FAHD1) DME0542 Homo sapiens
FAHD1_HUMAN
3.7.1.5
[4]
Phosphoenolpyruvate carboxykinase (PCK1) DME0496 Homo sapiens
PCKGC_HUMAN
4.1.1.32
[5]
⏷ Show the Full List of 6  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Oxaloacetate decarboxylase (FAHD1) DME0542 Km = 0.032 microM
FAHD1_HUMAN
[4]
Phosphoenolpyruvate carboxykinase (PCK1) DME0496 Km = 0.033 microM
PCKGC_HUMAN
[5]
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: 5236).
2 Mechanism of citrate metabolism by an oxaloacetate decarboxylase-deficient mutant of Lactococcus lactis IL1403
3 Reducing substrate inhibition of malate dehydrogenase from Geobacillus stearothermophilus by C-terminal truncation
4 Identification of FAH domain-containing protein 1 (FAHD1) as oxaloacetate decarboxylase. J Biol Chem. 2015 Mar 13;290(11):6755-62.
5 Tyr235 of human cytosolic phosphoenolpyruvate carboxykinase influences catalysis through an anion-quadrupole interaction with phosphoenolpyruvate carboxylate. FEBS J. 2008 Dec;275(23):5810-9.

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