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MedKoo Cat#: 534855 | Name: Mycothiazole

Description:

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

Mycothiazole is from cacospongia mycofijiensis.

Chemical Structure

Mycothiazole
Mycothiazole
CAS#114582-75-1

Theoretical Analysis

MedKoo Cat#: 534855

Name: Mycothiazole

CAS#: 114582-75-1

Chemical Formula: C22H32N2O3S

Exact Mass: 404.2134

Molecular Weight: 404.57

Elemental Analysis: C, 65.31; H, 7.97; N, 6.92; O, 11.86; S, 7.92

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
Mycothiazole
IUPAC/Chemical Name
Carbamic acid, ((4Z,7R)-8-(4-((2Z)-2,5-hexadienyl)-2-thiazolyl)-7-hydroxy-8-methyl-3-methylene-4-nonenyl)-, methyl ester
InChi Key
WOVFSYAJXQSJES-OEKGKEFLSA-N
InChi Code
InChI=1S/C22H32N2O3S/c1-6-7-8-9-12-18-16-28-20(24-18)22(3,4)19(25)13-10-11-17(2)14-15-23-21(26)27-5/h6,8-11,16,19,25H,1-2,7,12-15H2,3-5H3,(H,23,26)/b9-8-,11-10-/t19-/m1/s1
SMILES Code
O=C(OC)NCCC(/C=C\C[C@@H](O)C(C)(C1=NC(C/C=C\CC=C)=CS1)C)=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
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 404.57 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: Morgan JB, Mahdi F, Liu Y, Coothankandaswamy V, Jekabsons MB, Johnson TA, Sashidhara KV, Crews P, Nagle DG, Zhou YD. The marine sponge metabolite mycothiazole: a novel prototype mitochondrial complex I inhibitor. Bioorg Med Chem. 2010 Aug 15;18(16):5988-94. doi: 10.1016/j.bmc.2010.06.072. Epub 2010 Jun 25. PMID: 20637638; PMCID: PMC2918693. 2: Mahler G, Serra G, Dematteis S, Saldaña J, Domínguez L, Manta E. Synthesis and biological evaluation of simplified mycothiazole analogues. Bioorg Med Chem Lett. 2006 Mar 1;16(5):1309-11. doi: 10.1016/j.bmcl.2005.11.072. Epub 2005 Dec 27. PMID: 16384701. 3: Meyer KJ, Singh AJ, Cameron A, Tan AS, Leahy DC, O'Sullivan D, Joshi P, La Flamme AC, Northcote PT, Berridge MV, Miller JH. Mitochondrial genome-knockout cells demonstrate a dual mechanism of action for the electron transport complex I inhibitor mycothiazole. Mar Drugs. 2012 Apr;10(4):900-17. doi: 10.3390/md10040900. Epub 2012 Apr 16. PMID: 22690150; PMCID: PMC3366682. 4: Wang L, Hale KJ. Total Synthesis of the Potent HIF-1 Inhibitory Antitumor Natural Product, (8R)-Mycothiazole, via Baldwin-Lee CsF/CuI sp(3)-sp(2)-Stille Cross-Coupling. Confirmation of the Crews Reassignment. Org Lett. 2015 Sep 4;17(17):4200-3. doi: 10.1021/acs.orglett.5b01966. Epub 2015 Aug 14. PMID: 26271336. 5: Sonnenschein RN, Johnson TA, Tenney K, Valeriote FA, Crews P. A reassignment of (-)-mycothiazole and the isolation of a related diol. J Nat Prod. 2006 Jan;69(1):145-7. doi: 10.1021/np0503597. PMID: 16441088; PMCID: PMC2031212. 6: Johnson TA, Morris JD, Coppage DA, Cook CV, Persi LN, Ogarrio MA, Garcia TC, McIntosh NL, McCauley EP, Media J, Maheshwari M, Valeriote FA, Shaw J, Crews P. Reinvestigation of Mycothiazole Reveals the Penta-2,4-dien-1-ol Residue Imparts Picomolar Potency and 8S Configuration. ACS Med Chem Lett. 2020 Jan 2;11(2):108-113. doi: 10.1021/acsmedchemlett.9b00302. PMID: 32071675; PMCID: PMC7025380. 7: Le Flohic A, Meyer C, Cossy J. Total synthesis of (+/-)-mycothiazole and formal enantioselective approach. Org Lett. 2005 Jan 20;7(2):339-42. doi: 10.1021/ol047603q. PMID: 15646992. 8: Morrison RJ, van der Mei FW, Romiti F, Hoveyda AH. A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole. J Am Chem Soc. 2020 Jan 8;142(1):436-447. doi: 10.1021/jacs.9b11178. Epub 2019 Dec 24. PMID: 31873000; PMCID: PMC7017881. 9: Sugiyama H, Yokokawa F, Shioiri T. Asymmetric total synthesis of (-)-mycothiazole. Org Lett. 2000 Jul 13;2(14):2149-52. doi: 10.1021/ol000128l. PMID: 10891253. 10: Johnson TA, Sohn J, Inman WD, Estee SA, Loveridge ST, Vervoort HC, Tenney K, Liu J, Ang KK, Ratnam J, Bray WM, Gassner NC, Shen YY, Lokey RS, McKerrow JH, Boundy-Mills K, Nukanto A, Kanti A, Julistiono H, Kardono LB, Bjeldanes LF, Crews P. Natural product libraries to accelerate the high-throughput discovery of therapeutic leads. J Nat Prod. 2011 Dec 27;74(12):2545-55. doi: 10.1021/np200673b. Epub 2011 Nov 30. PMID: 22129061; PMCID: PMC3246535. 11: Johnson TA, Amagata T, Oliver AG, Tenney K, Valeriote FA, Crews P. The unexpected isolation of CTP-431, a novel thiopyrone from the sponge Cacospongia mycofijiensis. J Org Chem. 2008 Sep 19;73(18):7255-9. doi: 10.1021/jo801096m. Epub 2008 Aug 21. PMID: 18715038.