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ProductsBack/Heptelidic acid [57710-57-3]
Chemical Structure
Chemical Structure
Chemical Structure

Heptelidic acid [57710-57-3]

Research Use Only
AG-CN2-0118
AdipoGen Life Sciences
CAS Number57710-57-3
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Product group Chemicals
Estimated Purity>95%
Molecular Weight280.3
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Heptelidic acid [57710-57-3, 74310-84-2]
  • Delivery Days Customer
    10
  • CAS Number
    57710-57-3
  • Certification
    Research Use Only
  • Estimated Purity
    >95%
  • Hazard Information
    Warning
  • Molecular Formula
    C15H20O5
  • Molecular Weight
    280.3
  • Scientific Description
    Antibiotic [1, 2]. Potent selective glyceraldehyde 3-phosphate dehydrogenase (GAPDH) inhibitor. Binds to the essential Cys149 residue in the catalytic site of GAPDH [3-7, 10, 11]. Anticancer compound [8]. Selectively kills high-glycolytic cancer cells through glucose-dependent active ATP deprivation [12]. Antimalarial [9]. Apoptosis inhibitor. DNA fragmentation and caspase-3 activation inhibitor [13,16]. Selective and competitive inhibitor of mammalian DNA polymerases beta, lambda and terminal deoxynucleotidyl transferase (TdT) in family X of pols [14]. Reduces lactate secretion and causes reductions in overall protein synthesis and production of IFN-alpha and TNF. - Chemical. CAS: 57710-57-3 (74310-84-2 deleted). Formula: C15H20O5. MW: 280.3. Isolated from Trichoderma sp. Antibiotic. Potent selective glyceraldehyde 3-phosphate dehydrogenase (GAPDH) inhibitor. Binds to the essential Cys149 residue in the catalytic site of GADPH. Anticancer compound. Selectively kills high-glycolytic cancer cells through glucose-dependent active ATP deprivation. Antimalarial. Apoptosis inhibitor. DNA fragmentation and caspase-3 activation inhibitor. Selective and competitive inhibitor of mammalian DNA polymerases beta, lambda and terminal deoxynucleotidyl transferase (TdT) in family X of pols.
  • SMILES
    [H][C@@]12C=C(COC(=O)[C@@]1([H])[C@@]1(CO1)CC[C@H]2C(C)C)C(O)=O
  • Storage Instruction
    2°C to 8°C,-20°C
  • UNSPSC
    12352200

References

  • A new sesquiterpene antibiotic, heptelidic acid producing organisms, fermentation, isolation and characterization: Y. Itoh, et al.; J. Antibiot. (Tokyo) 33, 468 (1980)
  • Structure of heptelidic acid, a new sesquiterpene antibiotic from fungi: Y. Itoh, et al.; J. Antibiot. (Tokyo) 33, 525 (1980)
  • Specific inhibition of glyceraldehyde-3-phosphate dehydrogenase by koningic acid (heptelidic acid): A. Endo, et al.; J. Antibiot. (Tokyo) 38, 920 (1985)
  • Inactivation of rabbit muscle glyceraldehyde-3-phosphate dehydrogenase by koningic acid: K. Sakai, et al.; Biochim. Biophys. Acta 952, 297 (1988)
  • Identification of koningic acid (heptelidic acid)-modified site in rabbit muscle glyceraldehyde-3-phosphate dehydrogenase: K. Sakai, et al.; Biochim. Biophys. Acta 1077, 192 (1991)
  • Koningic acid (heptelidic acid) inhibition of glyceraldehyde-3-phosphate dehydrogenases from various sources: M. Kato, et al.; Biochim. Biophys. Acta 1120, 113 (1992)
  • Glyceraldehyde-3-phosphate dehydrogenase is required for the transport of nitric oxide in platelets: B. McDonald, et al.; PNAS 90, 11122 (1993)
  • Antitumor activity of heptelidic acid chlorohydrin: J. Kawashima, et al.; J. Antibiot. (Tokyo) 47, 1562 (1994)
  • Antimalarial activity of radicicol, heptelidic acid and other fungal metabolites: Y. Tanaka, et al.; J. Antibiot. (Tokyo) 51, 153 (1998)
  • Glyceraldehyde-3-phosphate dehydrogenase activity as an independent modifier of methylglyoxal levels in diabetes: P.J. Beisswenger, et al.; Biochim. Biophys. Acta 1637, 98 (2003)