Mycothiazole

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

MedKoo CAT#: 534855

CAS#: 114582-75-1

Description: Mycothiazole is from cacospongia mycofijiensis.


Chemical Structure

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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: 404.569
Elemental Analysis: C, 65.31; H, 7.97; N, 6.92; O, 11.86; S, 7.92

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

Preparing Stock Solutions

The following data is based on the product molecular weight 404.569 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

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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.