Heptelidic acid | CAS#57710-57-3 | esquiterpene lactone

MedKoo Cat#: 558572 | Name: Heptelidic acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Heptelidic acid is an esquiterpene lactone produced by the fungus T. koningii with antibiotic activity against anaerobic bacteria such as Bacteroides. It acts as an irreversible inhibitor of GAPDH that binds to the cysteine-149 residue at the active site of the enzyme.

Chemical Structure

Heptelidic acid

CAS#57710-57-3

Theoretical Analysis

MedKoo Cat#: 558572

Name: Heptelidic acid

CAS#: 57710-57-3

Chemical Formula: C15H20O5

Exact Mass: 280.1300

Molecular Weight: 280.32

Elemental Analysis: C, 64.27; H, 7.19; O, 28.54

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 750.00	2 Weeks

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Related CAS #

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Synonym

Heptelidic acid; Koningic acid; Heptelidate; Avocettin; (+)-Heptelidic acid;

IUPAC/Chemical Name

(5aS,6R,9S,9aS)-6-isopropyl-1-oxo-1,5a,6,7,8,9a-hexahydro-3H-spiro[benzo[c]oxepine-9,2'-oxirane]-4-carboxylic acid

InChi Key

JESMSCGUTIEROV-RTWAVKEYSA-N

InChi Code

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

SMILES Code

O=C(C1=C[C@@]2([H])[C@]([C@@]3(OC3)CC[C@@H]2C(C)C)([H])C(OC1)=O)O

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 280.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Sakai K, Hasumi K, Endo A. Two glyceraldehyde-3-phosphate dehydrogenase isozymes from the koningic acid (heptelidic acid) producer Trichoderma koningii. Eur J Biochem. 1990 Oct 5;193(1):195-202. PubMed PMID: 2226438. 2: Tanaka Y, Shiomi K, Kamei K, Sugoh-Hagino M, Enomoto Y, Fang F, Yamaguchi Y, Masuma R, Zhang CG, Zhang XW, Omura S. Antimalarial activity of radicicol, heptelidic acid and other fungal metabolites. J Antibiot (Tokyo). 1998 Feb;51(2):153-60. PubMed PMID: 9544936. 3: Sakai K, Hasumi K, Endo A. Identification of koningic acid (heptelidic acid)-modified site in rabbit muscle glyceraldehyde-3-phosphate dehydrogenase. Biochim Biophys Acta. 1991 Apr 8;1077(2):192-6. PubMed PMID: 2015292. 4: Kato M, Sakai K, Endo A. Koningic acid (heptelidic acid) inhibition of glyceraldehyde-3-phosphate dehydrogenases from various sources. Biochim Biophys Acta. 1992 Mar 27;1120(1):113-6. PubMed PMID: 1554737. 5: Kim JH, Lee CH. Heptelidic acid, a sesquiterpene lactone, inhibits Etoposide-induced apoptosis in human leukemia U937 cells. J Microbiol Biotechnol. 2009 Aug;19(8):787-91. PubMed PMID: 19734716. 6: Endo A, Hasumi K, Sakai K, Kanbe T. Specific inhibition of glyceraldehyde-3-phosphate dehydrogenase by koningic acid (heptelidic acid). J Antibiot (Tokyo). 1985 Jul;38(7):920-5. PubMed PMID: 4030504. 7: Rahier NJ, Molinier N, Long C, Deshmukh SK, Kate AS, Ranadive P, Verekar SA, Jiotode M, Lavhale RR, Tokdar P, Balakrishnan A, Meignan S, Robichon C, Gomes B, Aussagues Y, Samson A, Sautel F, Bailly C. Anticancer activity of koningic acid and semisynthetic derivatives. Bioorg Med Chem. 2015 Jul 1;23(13):3712-21. doi: 10.1016/j.bmc.2015.04.004. Epub 2015 Apr 9. PubMed PMID: 25937235. 8: Tanaka Y, Fang F, Zhang CH, Zhang XW, Omura S. Heme-dependent radical generation from antimalarial fungal metabolites, radicicol and heptelidic acid. J Antibiot (Tokyo). 1998 Apr;51(4):451-3. PubMed PMID: 9630871. 9: Itoh Y, Kodama K, Furuya K, Takahashi S, Haneishi T, Takiguchi Y, Arai M. A new sesquiterpene antibiotic, heptelidic acid producing organisms, fermentation, isolation and characterization. J Antibiot (Tokyo). 1980 May;33(5):468-73. PubMed PMID: 7191847. 10: Itoh Y, Takahashi S, Haneishi T, Arai M. Structure of heptelidic acid, a new sesquiterpene antibiotic from fungi. J Antibiot (Tokyo). 1980 May;33(5):525-6. PubMed PMID: 7429978. 11: Kawashima J, Ito F, Kato T, Niwano M, Koshino H, Uramoto M. Antitumor activity of heptelidic acid chlorohydrin. J Antibiot (Tokyo). 1994 Dec;47(12):1562-3. PubMed PMID: 7844052. 12: Yan S, Li S, Wu W, Zhao F, Bao L, Ding R, Gao H, Wen HA, Song F, Liu HW. Terpenoid and phenolic metabolites from the fungus xylaria sp. associated with termite nests. Chem Biodivers. 2011 Sep;8(9):1689-700. doi: 10.1002/cbdv.201100026. PubMed PMID: 21922657. 13: Yamaguchi Y, Manita D, Takeuchi T, Kuramochi K, Kuriyama I, Sugawara F, Yoshida H, Mizushina Y. Novel terpenoids, trichoderonic acids A and B isolated from Trichoderma virens, are selective inhibitors of family X DNA polymerases. Biosci Biotechnol Biochem. 2010;74(4):793-801. Epub 2010 Apr 7. PubMed PMID: 20378979. 14: Watanabe H, Hasumi K, Fukushima Y, Sakai K, Endo A. Cloning of two isozymes of Trichoderma koningii glyceraldehyde-3-phosphate dehydrogenase with different sensitivity to koningic acid. Biochim Biophys Acta. 1993 Feb 20;1172(1-2):43-8. PubMed PMID: 8439569. 15: Peng X, Gong F, Chen Y, Jiang Y, Liu J, Yu M, Zhang S, Wang M, Xiao G, Liao H. Autophagy promotes paclitaxel resistance of cervical cancer cells: involvement of Warburg effect activated hypoxia-induced factor 1-α-mediated signaling. Cell Death Dis. 2014 Aug 14;5:e1367. doi: 10.1038/cddis.2014.297. PubMed PMID: 25118927; PubMed Central PMCID: PMC4454295. 16: Sakai K, Hasumi K, Endo A. Inactivation of rabbit muscle glyceraldehyde-3-phosphate dehydrogenase by koningic acid. Biochim Biophys Acta. 1988 Feb 10;952(3):297-303. PubMed PMID: 3337830. 17: Nakazawa M, Uehara T, Nomura Y. Koningic acid (a potent glyceraldehyde-3-phosphate dehydrogenase inhibitor)-induced fragmentation and condensation of DNA in NG108-15 cells. J Neurochem. 1997 Jun;68(6):2493-9. PubMed PMID: 9166744. 18: Kumagai S, Narasaki R, Hasumi K. Glucose-dependent active ATP depletion by koningic acid kills high-glycolytic cells. Biochem Biophys Res Commun. 2008 Jan 11;365(2):362-8. Epub 2007 Nov 13. PubMed PMID: 17997978. 19: Cane DE, Sohng JK. Inhibition of glyceraldehyde-3-phosphate dehydrogenase by pentalenolactone. 2. Identification of the site of alkylation by tetrahydropentalenolactone. Biochemistry. 1994 May 31;33(21):6524-30. PubMed PMID: 8204587. 20: McDonald B, Reep B, Lapetina EG, Molina y Vedia L. Glyceraldehyde-3-phosphate dehydrogenase is required for the transport of nitric oxide in platelets. Proc Natl Acad Sci U S A. 1993 Dec 1;90(23):11122-6. PubMed PMID: 7902582; PubMed Central PMCID: PMC47934.