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MedKoo Cat#: 413548 | Name: Depudecin

Description:

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

Depudecin is a polyketide obtained from the fungus Alternaria brassicicola and having a highly unusual structure of an 11-carbon chain containing two epoxides and six stereogenic centres. It is an inhibitor of histone deacetylase (HDAC) both in vivo and in vitro and also exhibits anti-angiogenic activity.

Chemical Structure

Depudecin
Depudecin
CAS#139508-73-9

Theoretical Analysis

MedKoo Cat#: 413548

Name: Depudecin

CAS#: 139508-73-9

Chemical Formula: C11H16O4

Exact Mass: 212.1049

Molecular Weight: 212.25

Elemental Analysis: C, 62.25; H, 7.60; O, 30.15

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Depudecin
IUPAC/Chemical Name
Oxiranemethanol, alpha-ethenyl-3-(2-(3-(1-hydroxyethyl)oxiranyl)ethenyl)-, (2S-(2R*(E(2R*(S*),3R*)),3R*(S*)))-
InChi Key
DLVJMFOLJOOWFS-HANANGGRSA-N
InChi Code
InChI=1S/C11H16O4/c1-3-7(13)11-9(15-11)5-4-8-10(14-8)6(2)12/h3-13H,1H2,2H3/b5-4+/t6?,7?,8?,9-,10?,11-/m0/s1
SMILES Code
OC(C=C)[C@@H]1O[C@H]1/C=C/C2OC2C(O)C
Appearance
Solid powder
Purity
>98% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 212.25 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.

Recalculate based on batch purity %
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: Cheng-Sánchez I, García-Ruiz C, Guerrero-Vásquez GA, Sarabia F. An Olefin Cross-Metathesis Approach to Depudecin and Stereoisomeric Analogues. J Org Chem. 2017 May 5;82(9):4744-4757. doi: 10.1021/acs.joc.7b00424. Epub 2017 Apr 19. PMID: 28397496. 2: García-Ruiz C, Cheng-Sánchez I, Sarabia F. Stereoselective Total Synthesis of (-)-Depudecin. Org Lett. 2015 Nov 20;17(22):5558-61. doi: 10.1021/acs.orglett.5b02697. Epub 2015 Oct 30. PMID: 26517569. 3: Privalsky ML. Depudecin makes a debut. Proc Natl Acad Sci U S A. 1998 Mar 31;95(7):3335-7. doi: 10.1073/pnas.95.7.3335. PMID: 9520362; PMCID: PMC33845. 4: Kwon HJ, Owa T, Hassig CA, Shimada J, Schreiber SL. Depudecin induces morphological reversion of transformed fibroblasts via the inhibition of histone deacetylase. Proc Natl Acad Sci U S A. 1998 Mar 31;95(7):3356-61. doi: 10.1073/pnas.95.7.3356. PMID: 9520369; PMCID: PMC19839. 5: Wight WD, Kim KH, Lawrence CB, Walton JD. Biosynthesis and role in virulence of the histone deacetylase inhibitor depudecin from Alternaria brassicicola. Mol Plant Microbe Interact. 2009 Oct;22(10):1258-67. doi: 10.1094/MPMI-22-10-1258. PMID: 19737099. 6: Matsumoto M, Matsutani S, Sugita K, Yoshida H, Hayashi F, Terui Y, Nakai H, Uotani N, Kawamura Y, Matsumoto K, et al. Depudecin: a novel compound inducing the flat phenotype of NIH3T3 cells doubly transformed by ras- and src-oncogene, produced by Alternaria brassicicola. J Antibiot (Tokyo). 1992 Jun;45(6):879-85. doi: 10.7164/antibiotics.45.879. PMID: 1500354. 7: Tanaka M, Fujimori T, Nabeta K. Biosynthesis of depudecin, a metabolite of Nimbya scirpicola. Biosci Biotechnol Biochem. 2000 Feb;64(2):244-7. doi: 10.1271/bbb.64.244. PMID: 10737176. 8: Zhong W, Huang C, Lin J, Zhu M, Zhong H, Chiang MH, Chiang HS, Hui MS, Lin Y, Huang J. Development and Validation of Nine-RNA Binding Protein Signature Predicting Overall Survival for Kidney Renal Clear Cell Carcinoma. Front Genet. 2020 Oct 2;11:568192. doi: 10.3389/fgene.2020.568192. PMID: 33133154; PMCID: PMC7566920. 9: Sugita K, Yoshida H, Matsumoto M, Matsutani S. A novel compound, depudecin, induces production of transformation to the flat phenotype of NIH3T3 cells transformed by ras-oncogene. Biochem Biophys Res Commun. 1992 Jan 15;182(1):379-87. doi: 10.1016/s0006-291x(05)80156-1. PMID: 1731795. 10: Kwon HJ, Kim JH, Kim M, Lee JK, Hwang WS, Kim DY. Anti-parasitic activity of depudecin on Neospora caninum via the inhibition of histone deacetylase. Vet Parasitol. 2003 Mar 25;112(4):269-76. doi: 10.1016/s0304-4017(03)00035-9. PMID: 12623206.

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