A selective, irreversible GAPDH inhibitor
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Heptelidic Acid

Item No. 14079

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2'S,5aS,6R,9aS)-1,5a,6,7,8,9a-hexahydro-6-(1-methylethyl)-1-oxo-spiro[2-benzoxepin-9(3H),2'-oxirane]-4-carboxylic acid
CAS Number
57710-57-3
Synonyms
  • Avocettin
  • BRN 5091359
  • FO-4443
  • Koningic Acid
Molecular Formula
C15H20O5
Formula Weight
280.3
Purity
≥95%
Formulation (Request formulation change)
A film
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
217 nm
SMILES
CC(C)[C@H]1CC[C@@]2(CO2)[C@]3([H])[C@]1([H])C=C(C(O)=O)COC3=O
InChi Code
InChI=1S/C15H20O5/c1-8(2)10-3-4-15(7-20-15)12-11(10)5-9(13(16)17)6-19-14(12)18/h5,8,10-12H,3-4,6-7H2,1-2H3,(H,16,17)/t10-,11-,12-,15-/m1/s1
InChi Key
JESMSCGUTIEROV-RTWAVKEYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    250 µg

    $153

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    1 mg

    $459

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    Product Description

    Heptelidic acid is a sesquiterpene lactone produced by the fungus T. koningii that was shown to have antibiotic activity against anaerobic bacteria such as Bacteroides.1 It acts as an irreversible inhibitor of GAPDH that binds to the cysteine-149 residue at the active site of the enzyme (Ki = 1.6 µM).2 It can selectively induce apoptosis in high-glycolytic cancer cells by inhibiting the generation of ATP in the glycolytic pathway.3 Heptelidic acid is also a selective and competitive inhibitor of mammalian DNA polymerases β and λ as well as terminal deoxynucleotidyl transferase in family X of DNA polymerases (Kis range from 5.2-9.5 µM).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Endo, A., Hasumi, K., Sakai, K., et al. Specific inhibition of glyceraldehyde-3-phosphate dehydrogenase by koningic acid (heptelidic acid). J. Antibiot. (Tokyo) 38(7), 920-925 (1985).

    2. Sakai, K., Hasumi, K., and Endo, A. Identification of koningic acid (heptelidic acid)-modified site in rabbit muscle glyceraldehyde-3-phosphate dehydrogenase. Biochim. Biophys. Acta 1077(2), 192-196 (1991).

    3. Kumagai, S., Narasaki, R., and Hasumi, K. Glucose-dependent active ATP depletion by koningic acid kills high-glycolytic cells. Biochem. Biophys. Res. Commun. 365(2), 362-368 (2008).

    4. Yamaguchi, Y., Manita, D., Takeuchi, T., et al. Novel terpenoids, trichoderonic acids A and B isolated from Trichoderma virens, are selective inhibitors of family X DNA polymerases. Biosci. Biotechnol. Biochem. 74(4), 793-801 (2010).

    Product Citations

    Kremer, D.M., Nelson, B.S., Lin, L., et al. GOT1 inhibition primes pancreatic cancer for ferroptosis through the autophagic release of labile iron. bioRxiv (2020).

    Angelin, A., Gil-de-Gómez, L., Dahiya, S., et al. Foxp3 reprograms T cell metabolism to function in low-glucose, high-lactate environments. Cell. Metab. 25(6), 1282-1293 (2017).