heptelidic acid
koningic acid
Identification
| Name | heptelidic 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 Number | 57710-57-3 |
| FDA UNII | 6H8EDV2NKQ |
| Molecular Formula | C15 H20 O5 |
| Molecular Weight | 280.32040000 |
| Beilstein | 5091359 |
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 Toxicity | intraperitoneal-mouse LD50 32 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for heptelidic acid usage levels up to | not for fragrance use. |
| Recommendation for heptelidic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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.