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

General Information of Drug (ID: DR2123)
Drug Name
Phosphoenolpyruvate
Synonyms
P-enol-pyruvate; P-enolpyruvate; Phospho(enol)pyruvic acid; Phosphoenolpyruvic acid; Phosphopyruvic acid; phosphoenolpyruvate; 138-08-9; 1nhx; 2-(phosphonooxy)-2-propenoic acid; 2-(phosphonooxy)prop-2-enoic acid; 2-Dihydroxyphosphinoyloxyacrylic acid; 2-Phosphonooxyprop-2-enoic acid; 2-Propenoic acid, 2-(phosphonooxy)-; 2-phosphonooxyprop-2-enoate; 545YL308OW; 923-14-8; AC1L1AIQ; Barium silver 2-(phosphonatooxy)acrylate; CHEBI:44897; EINECS 205-312-2; EINECS 213-089-8; PEP; UNII-545YL308OW; bmse000107; DTBNBXWJWCWCIK-UHFFFAOYSA-N
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 168.04 Topological Polar Surface Area 104
Heavy Atom Count 10 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
1005
PubChem SID
3374 ; 583652 ; 584923 ; 820197 ; 820473 ; 827615 ; 828410 ; 828556 ; 828558 ; 828817 ; 854810 ; 4790277 ; 7889796 ; 8009228 ; 8009230 ; 8009232 ; 8013976 ; 8020252 ; 8020259 ; 8025541 ; 8150924 ; 11538112 ; 14772543 ; 24277639 ; 24439362 ; 24697526 ; 24697892 ; 24775896 ; 24874887 ; 26697124 ; 26717277 ; 26737585 ; 46392608 ; 46506098 ; 49681292 ; 49703243 ; 57320663 ; 57410861 ; 57578075 ; 57654765 ; 75356424 ; 81064563 ; 85164943 ; 85856284 ; 92298602 ; 99239587 ; 99239589 ; 104251378 ; 104296495 ; 124361194
ChEBI ID
CHEBI:44897
CAS Number
138-08-9
TTD Drug ID
D0T3AE
Formula
C3H5O6P
Canonical SMILES
C=C(C(=O)O)OP(=O)(O)O
InChI
1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
InChIKey
DTBNBXWJWCWCIK-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
Oxaloacetate DM003435
970
Unclear 1 [5]
PYR DM000331
107735
Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007591 Phosphoenolpyruvate Pyruvate Unclear PKM2 [3]
MR007592 Phosphoenolpyruvate Oxaloacetate Unclear PCK1 [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Phosphoenolpyruvate carboxykinase (PCK1) DME0496 Homo sapiens
PCKGC_HUMAN
4.1.1.32
[2]
pyruvate kinase M2 (PKM2) DMEN373 Homo sapiens
KPYM_HUMAN
2.7.1.40
[3]
Red cell/liver pyruvate kinase (PKLR) DME0497 Homo sapiens
KPYR_HUMAN
2.7.1.40
[4]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Phosphoenolpyruvate carboxykinase (PCK1) DME0496 Km = 0.036 microM
PCKGC_HUMAN
[2]
Red cell/liver pyruvate kinase (PKLR) DME0497 Km = 0.112 microM
KPYR_HUMAN
[4]
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: 4692).
2 Tyr235 of human cytosolic phosphoenolpyruvate carboxykinase influences catalysis through an anion-quadrupole interaction with phosphoenolpyruvate carboxylate. FEBS J. 2008 Dec;275(23):5810-9.
3 Pyruvate kinase M2: A simple molecule with complex functions
4 Energetic coupling between an oxidizable cysteine and the phosphorylatable N-terminus of human liver pyruvate kinase. Biochemistry. 2013 Jan 22;52(3):466-76.
5 Exploring Amino Sugar and Phosphoenolpyruvate Metabolism to Improve Escherichia coli N-Acetylneuraminic Acid Production

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