heptelidic acid

koningic acid

CAS: 57710-57-3 C15 H20 O5 MW: 280.32040000

Identification

Nameheptelidic acid
IUPAC(5aS,9S,9aS)-1-oxo-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-4-carboxylic acid
CAS Number57710-57-3
FDA UNII6H8EDV2NKQ
Molecular FormulaC15 H20 O5
Molecular Weight280.32040000
Beilstein5091359

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 501.12 °C. @ 760.00 mm Hg (est)
Flash Point 372.00 °F. TCC ( 189.10 °C. ) (est)
logP (o/w) 2.034 (est)
Soluble in water, 2192 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral Toxicityintraperitoneal-mouse LD50 32 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for heptelidic acid usage levels up tonot for fragrance use.
Recommendation for heptelidic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

avocettin 3,5a,6,7,8,9a- hexahydro-6-isopropyl-1-oxospiro(1H-2-benzoxepin-9,2'-oxirane)-4-carboxylic acid koningic acid (5aS,9S,9aS)-1-oxo-6- propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-4-carboxylic acid PubMed: Autophagy promotes paclitaxel resistance of cervical cancer cells: involvement of Warburg effect activated hypoxia-induced factor 1-α-mediated signaling. PubMed: Inhibition of glycolysis attenuates 4-hydroxynonenal-dependent autophagy and exacerbates apoptosis in differentiated SH-SY5Y neuroblastoma cells. PubMed: Terpenoid and phenolic metabolites from the fungus xylaria sp. associated with termite nests. PubMed: Glyceraldehyde 3-phosphate dehydrogenase is unlikely to mediate hydrogen peroxide signaling: studies with a novel anti-dimedone sulfenic acid antibody. PubMed: Novel terpenoids, trichoderonic acids A and B isolated from Trichoderma virens, are selective inhibitors of family X DNA polymerases. PubMed: Heptelidic acid, a sesquiterpene lactone, inhibits Etoposide-induced apoptosis in human leukemia U937 cells. PubMed: Glucose-dependent active ATP depletion by koningic acid kills high-glycolytic cells. PubMed: Mechanism of the stress-induced collapse of the Ran distribution. PubMed: The glycolytic enzyme glyceraldehyde-3-phosphate dehydrogenase works as an arsenate reductase in human red blood cells and rat liver cytosol. PubMed: D-Glyceraldehyde causes production of intracellular peroxide in pancreatic islets, oxidative stress, and defective beta cell function via non-mitochondrial pathways. PubMed: Hydrogen peroxide induces association between glyceraldehyde 3-phosphate dehydrogenase and phospholipase D2 to facilitate phospholipase D2 activation in PC12 cells. PubMed: Glyceraldehyde-3-phosphate dehydrogenase activity as an independent modifier of methylglyoxal levels in diabetes. PubMed: A transient brain ischemia- and bacterial endotoxin-induced glial iNOS expression and NO-induced neuronal apoptosis. PubMed: Heme-dependent radical generation from antimalarial fungal metabolites, radicicol and heptelidic acid. PubMed: Antimalarial activity of radicicol, heptelidic acid and other fungal metabolites. PubMed: Koningic acid (a potent glyceraldehyde-3-phosphate dehydrogenase inhibitor)-induced fragmentation and condensation of DNA in NG108-15 cells. PubMed: Antitumor activity of heptelidic acid chlorohydrin. PubMed: Inhibition of glyceraldehyde-3-phosphate dehydrogenase by pentalenolactone. 2. Identification of the site of alkylation by tetrahydropentalenolactone. PubMed: Inhibition of glyceraldehyde-3-phosphate dehydrogenase by phosphorylated epoxides and alpha-enones. PubMed: A glyceraldehyde-3-phosphate dehydrogenase with eubacterial features in the amitochondriate eukaryote, Trichomonas vaginalis. PubMed: Glyceraldehyde-3-phosphate dehydrogenase is required for the transport of nitric oxide in platelets. PubMed: Cloning of two isozymes of Trichoderma koningii glyceraldehyde-3-phosphate dehydrogenase with different sensitivity to koningic acid. PubMed: Koningic acid (heptelidic acid) inhibition of glyceraldehyde-3-phosphate dehydrogenases from various sources. PubMed: Identification of koningic acid (heptelidic acid)-modified site in rabbit muscle glyceraldehyde-3-phosphate dehydrogenase. PubMed: Two glyceraldehyde-3-phosphate dehydrogenase isozymes from the koningic acid (heptelidic acid) producer Trichoderma koningii. PubMed: Inactivation of rabbit muscle glyceraldehyde-3-phosphate dehydrogenase by koningic acid. PubMed: Specific inhibition of glyceraldehyde-3-phosphate dehydrogenase by koningic acid (heptelidic acid). PubMed: Structure of heptelidic acid, a new sesquiterpene antibiotic from fungi. PubMed: A new sesquiterpene antibiotic, heptelidic acid producing organisms, fermentation, isolation and characterization.