ChemicalBook--->CAS DataBase List--->74310-84-2

74310-84-2

74310-84-2 Structure

74310-84-2 Structure
IdentificationBack Directory
[Name]

Heptelidic acid
[CAS]

74310-84-2
[Synonyms]

Heptelidic acid (Koningic acid)
[Molecular Formula]

C15H20O5
[MDL Number]

MFCD01684016
[MOL File]

74310-84-2.mol
[Molecular Weight]

280.316
Chemical PropertiesBack Directory
[storage temp. ]

-20°C
[solubility ]

Soluble in water (up to 1 mg/ml) or in DMSO
[form ]

solid
[color ]

Off-white
[Stability:]

Stable for 1 year from date of purchase as supplied. Solutions in distilled water or DMSO may be stored at -20°C for up to 1 month.
Hazard InformationBack Directory
[Description]

Koningic acid (KA; 74310-84-2) is a potent and selective inhibitor of glyceraldehyde-3-phosphate dehydrogenase (GAPDH).1? Inhibition is irreversible and proceeds via nucleophilic attack of an active site cysteine on the epoxide moiety2, Ki = 1.1 μM for rabbit muscle GAPDH3. KA can selectively kill high-glycolytic cancer cells via glucose dependent ATP depletion.4 Has been used in a predictive model for selective targeting of the Warburg effect, the most prominent hallmark of cancer cell metabolism.5
[Uses]

Heptelidic acid is an inhibitor of GAPDH and certain DNA polymerases.
[References]

1) Endo et al. (1985), Specific inhibition of glyceraldehyde-3-phosphate dehydrogenase by koningic acid (heptelidic acid); J. Antibiot., 38 920 2) Sakai et al. (1991), Identification of koningic acid (heptelidic acid)-modified site in rabbit muscle glyceraldehyde-3-phosphate dehydrogenase; Biochim. Biophys. Acta, 1077 192 3) Sakai et al. (1988), Inactivation of rabbit muscle glyceraldehyde-3-phosphate dehydrogenase by koningic acid; Biochim. Biophys. Acta, 952 297 4) Kumagai et al. (2008), Glucose-dependent active ATP depletion by koningic acid kills high-glycolytic cells; Biochem. Biophys. Res. Commun. 365 362 5) Liberti et al. (2017), A Predictive Model for Selective Targeting of the Warburg Effect through GAPDH Inhibition with a Natural Product; Cell Metab., 26 648
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