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Chemical structure of Koningic acid

GB40253

Koningic acid

Also known as 1-oxo-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-4-carboxylic acid

Koningic acid (KA; 74310-84-2) is a potent and selective inhibitor of glyceraldehyde-3-phosphate dehydrogenase (GAPDH)· Inhibition is irreversible and proceeds via nucleophilic attack of an active site cysteine on the epoxide moiety, Ki = 1·1 μM for rabbit muscle GAPDH· KA can selectively kill high-glycolytic cancer cells via glucose dependent ATP depletion· Has been used in a predictive model for selective targeting of the Warburg effect, the most prominent hallmark of cancer cell metabolism

ChemicalCAS74310-84-2MW280.32FormulaC15H20O5
CAS number
74310-84-2
Molecular weight
280.32
Formula
C15H20O5
InChIKey
JESMSCGUTIEROV-UHFFFAOYSA-N
Catalogue number
GB40253
Brand
GLPBIO
Computed properties PubChem CID 10016502 · XLogP 1.4 · TPSA 76.1 Ų · H-bond donors 1
XLogP
1.4
TPSA
76.1 Ų
H-bond donors
1
H-bond acceptors
5
Rotatable bonds
2
Heavy atoms
20

SMILES CC(C)C1CCC2(CO2)C3C1C=C(COC3=O)C(=O)O

Computed descriptors from PubChem (CID 10016502), public domain. Identity cross-checked against the supplier's molecular formula and weight — verify before use.

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