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MedKoo Cat#: 525340 | Name: Cyslabdan

Description:

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

Cyslabdan is an inhibitor of Pentaglycine Interpeptide Bridge Synthesis.

Chemical Structure

Cyslabdan
Cyslabdan
CAS#956507-17-8

Theoretical Analysis

MedKoo Cat#: 525340

Name: Cyslabdan

CAS#: 956507-17-8

Chemical Formula: C25H41NO5S

Exact Mass: 467.2705

Molecular Weight: 467.67

Elemental Analysis: C, 64.21; H, 8.84; N, 3.00; O, 17.11; S, 6.86

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
Cyslabdan
IUPAC/Chemical Name
N-acetyl-S-(((1R,2S,3S,8aS)-2,3-dihydroxy-5,5,8a-trimethyl-1-((E)-3-methylpenta-2,4-dien-1-yl)decahydronaphthalen-2-yl)methyl)-L-cysteine
InChi Key
PSUMRJNLBIVEFF-HSBZVRLGSA-N
InChi Code
InChI=1S/C25H41NO5S/c1-7-16(2)9-10-19-24(6)12-8-11-23(4,5)20(24)13-21(28)25(19,31)15-32-14-18(22(29)30)26-17(3)27/h7,9,18-21,28,31H,1,8,10-15H2,2-6H3,(H,26,27)(H,29,30)/b16-9+/t18-,19+,20?,21-,24+,25-/m0/s1
SMILES Code
C[C@@]12C(C[C@H](O)[C@@](CSC[C@H](NC(C)=O)C(O)=O)(O)[C@@H]2C/C=C(C=C)\C)C(C)(C)CCC1
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
Soluble in DMSO
Shelf Life
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 467.67 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: Také A, Matsumoto A, Ōmura S, Takahashi Y. Corrigendum: Streptomyces lactacystinicus sp. nov. and Streptomyces cyslabdanicus sp. nov., producing lactacystin and cyslabdan, respectively. J Antibiot (Tokyo). 2017 Jan;70(1):113. doi: 10.1038/ja.2016.103. PubMed PMID: 28053352. 2: Ohtawa M, Hishinuma Y, Takagi E, Yamada T, Ito F, Arima S, Uchida R, Kim YP, Ōmura S, Tomoda H, Nagamitsu T. Synthesis and Structural Revision of Cyslabdan. Chem Pharm Bull (Tokyo). 2016;64(9):1370-7. doi: 10.1248/cpb.c16-00382. PubMed PMID: 27581641. 3: Tomoda H. New Approaches to Drug Discovery for Combating MRSA. Chem Pharm Bull (Tokyo). 2016;64(2):104-11. doi: 10.1248/cpb.c15-00743. Review. PubMed PMID: 26833438. 4: Také A, Matsumoto A, Ōmura S, Takahashi Y. Streptomyces lactacystinicus sp. nov. and Streptomyces cyslabdanicus sp. nov., producing lactacystin and cyslabdan, respectively. J Antibiot (Tokyo). 2015 Nov;68(11):719. doi: 10.1038/ja.2015.89. PubMed PMID: 26612144. 5: Ikeda H, Shin-Ya K, Nagamitsu T, Tomoda H. Biosynthesis of mercapturic acid derivative of the labdane-type diterpene, cyslabdan that potentiates imipenem activity against methicillin-resistant Staphylococcus aureus: cyslabdan is generated by mycothiol-mediated xenobiotic detoxification. J Ind Microbiol Biotechnol. 2016 Mar;43(2-3):325-42. doi: 10.1007/s10295-015-1694-6. Epub 2015 Oct 27. PubMed PMID: 26507838. 6: Shanthi J, Senthil A, Gopikrishnan V, Balagurunathan R. Characterization of a potential β-lactamase inhibitory metabolite from a marine Streptomyces sp. PM49 active against multidrug-resistant pathogens. Appl Biochem Biotechnol. 2015 Apr;175(8):3696-708. doi: 10.1007/s12010-015-1538-x. Epub 2015 Mar 5. PubMed PMID: 25737024. 7: Také A, Matsumoto A, Ōmura S, Takahashi Y. Streptomyces lactacystinicus sp. nov. and Streptomyces cyslabdanicus sp. nov., producing lactacystin and cyslabdan, respectively. J Antibiot (Tokyo). 2015 May;68(5):322-7. doi: 10.1038/ja.2014.162. Epub 2014 Dec 10. Erratum in: J Antibiot (Tokyo). 2015 Nov;68(11):719. PubMed PMID: 25491896. 8: Koyama N, Inokoshi J, Tomoda H. Anti-infectious agents against MRSA. Molecules. 2012 Dec 24;18(1):204-24. doi: 10.3390/molecules18010204. Review. PubMed PMID: 23262449. 9: Koyama N, Tokura Y, Münch D, Sahl HG, Schneider T, Shibagaki Y, Ikeda H, Tomoda H. The nonantibiotic small molecule cyslabdan enhances the potency of β-lactams against MRSA by inhibiting pentaglycine interpeptide bridge synthesis. PLoS One. 2012;7(11):e48981. doi: 10.1371/journal.pone.0048981. Epub 2012 Nov 6. PubMed PMID: 23166602; PubMed Central PMCID: PMC3490914. 10: Tomoda H. [Mode of action of microbial anti-MRSA agents]. Yakugaku Zasshi. 2012;132(1):37-44. Review. Japanese. PubMed PMID: 22214578. 11: Fukumoto A, Kim YP, Hanaki H, Shiomi K, Tomoda H, Omura S. Cyslabdan, a new potentiator of imipenem activity against methicillin-resistant Staphylococcus aureus, produced by Streptomyces sp. K04-0144. II. Biological activities. J Antibiot (Tokyo). 2008 Jan;61(1):7-10. doi: 10.1038/ja.2008.102. PubMed PMID: 18305353. 12: Fukumoto A, Kim YP, Matsumoto A, Takahashi Y, Shiomi K, Tomoda H, Omura S. Cyslabdan, a new potentiator of imipenem activity against methicillin-resistant Staphylococcus aureus, produced by Streptomyces sp. K04-0144. I. Taxonomy, fermentation, isolation and structural elucidation. J Antibiot (Tokyo). 2008 Jan;61(1):1-6. doi: 10.1038/ja.2008.101. PubMed PMID: 18305352.

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