Heptelidic acid (Koningic acid), GAPDH inhibitor

Key facts

CAS number

57710-57-3

Purity

>95%

Form

Solid

form

Source

Trichoderma sp.

Molecular weight

280.32 Da

Molecular formula

C₁₅H₂₀O₅

PubChem

10945834

Nature

Native

Solubility

Soluble in DMSO (10 mg/ml)

Soluble in ethanol (1 mg/ml)

Soluble in methanol (1 mg/ml)

Soluble in water (1 mg/ml)

Biochemical name

Heptelidic acid

Biological description

Potent, selective, irreversible GAPDH inhibitor. Selective, competitive DNA polymerase inhibitor. Antibiotic agent. Potently inhibits ATP generation in the glycolytic pathway. Inhibits DNA polymerases β, λ and terminal deoxynucleotidyl transferase (TdT) in family X. Inhibits caspase- 3 induction (IC₅₀ = 40 μM). Shows antiapoptotic effects.

Canonical smiles

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

Isomeric smiles

CC(C)[C@H]1CC[C@@]2(CO2)[C@@H]3[C@@H]1C=C(COC3=O)C(=O)O

InChi

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

InChiKey

JESMSCGUTIEROV-RTWAVKEYSA-N

IUPAC Name

(5aS,6R,9S,9aS)-1-oxo-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-4-carboxylic acid