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AdipoGen Life Sciences
Heptelidic acid
140
CHF
CHF 140.00
In stock
AG-CN2-0118-C250250 µgCHF 140.00
AG-CN2-0118-M0011 mgCHF 420.00
| Product Details | |
|---|---|
| Synonyms | Koningic acid; Avocettin; FO-4443; BRN 5091359; HPA |
| Product Type | Chemical |
| Properties | |
| Formula |
C15H20O5 |
| MW | 280.3 |
| CAS | 57710-57-3 (74310-84-2 deleted) |
| Source/Host Chemicals | Isolated from Trichoderma sp. |
| Purity Chemicals | ≥95% (HPLC) |
| Appearance | White solid. |
| Solubility | Soluble in DMSO (10mg/ml), ethanol (1mg/ml), methanol (1mg/ml) or water (1mg/ml). |
| InChi Key | JESMSCGUTIEROV-RTWAVKEYSA-N |
| Smiles | [H][C@@]12C=C(COC(=O)[C@@]1([H])[C@@]1(CO1)CC[C@H]2C(C)C)C(O)=O |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Handling Advice | Keep cool and dry. |
| Use/Stability | Stable for at least 3 years after receipt when stored at -20°C. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
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-α and TNF.
Product 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)
- D-Glyceraldehyde causes production of intracellular peroxide in pancreatic islets, oxidative stress, and defective beta cell function via non-mitochondrial pathways: H. Takahashi, et al.; J. Biol. Chem. 279, 37316 (2004)
- Glucose-dependent active ATP depletion by koningic acid kills high-glycolytic cells: S. Kumagai, et al.; BBRC 365, 362 (2008)
- Heptelidic acid, a sesquiterpene lactone, inhibits Etoposide-induced apoptosis in human leukemia U937 cells: J.H. Kim & C.H. Lee; J. Microbiol. Biotechnol. 19, 787 (2009)
- Novel terpenoids, trichoderonic acids A and B isolated from Trichoderma virens, are selective inhibitors of family X DNA polymerases: Y. Yamaguchi, et al.; Biosci. Biotechnol. Biochem. 74, 793 (2010)
- Rapid effector function of memory CD8+ T cells requires an immediate-early glycolytic switch: P. M. Gubser, et al.; Nat. Immunol. 14, 1064 (2013)
- The immune-metabolic basis of effector memory CD4+ T cell function under hypoxic conditions: S. Dimeloe, et al.; J. Immunol. 196, 106 (2016)
- ATP produced by anaerobic glycolysis is essential for enucleation of human erythroblasts: T. Goto, et al.; Exp. Hematol. 72, 14 (2019)
- Probiotic Aspergillus oryzae produces anti-tumor mediator and exerts anti-tumor effects in pancreatic cancer through the p38 MAPK signaling pathway: H. Konishi, et al.; Nat. Sci. Rep. 11, 11070 (2021)
- Plasmacytoid dendritic cell activation is dependent on coordinated expression of distinct amino acid transporters: K.M. Grzes, et al.; Immunity 54, 2514 (2021)
- Probiotic-derived heptelidic acid exerts antitumor effects on extraintestinal melanoma through glyceraldehyde-3-phosphate dehydrogenase activity control: S. Isozaki, et al.; BMC Microbiol. 22, 110 (2022)
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