(4R,5S)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2S)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienamide

• ChemBase ID: 154721
• Molecular Formular: C25H33N3O3S2
• Molecular Mass: 487.67782
• Monoisotopic Mass: 487.19633393
• SMILES: C[C@@H](/C=C/C=C/C(C)C)c1nc(cs1)c1nc(cs1)/C=C/[C@@H]([C@@H](C)/C(=C/C(=O)N)/OC)OC
• Canonical SMILES: CO[C@H]([C@H](/C(=C/C(=O)N)/OC)C)/C=C/c1csc(n1)c1csc(n1)[C@H](/C=C/C=C/C(C)C)C
• InChI: InChI=1S/C25H33N3O3S2/c1-16(2)9-7-8-10-17(3)24-28-20(15-33-24)25-27-19(14-32-25)11-12-21(30-5)18(4)22(31-6)13-23(26)29/h7-18,21H,1-6H3,(H2,26,29)/t17-,18+,21-/m0/s1
• InChIKey: XKTFQMCPGMTBMD-UEXGIBASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2S)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienamide
• IUPAC Traditional name: (4R,5S)-3,5-dimethoxy-4-methyl-7-(2-{2-[(2S)-7-methylocta-3,5-dien-2-yl]-1,3-thiazol-4-yl}-1,3-thiazol-4-yl)hepta-2,6-dienamide
• Synonyms: Myxothiazol

Database IDs

• CAS Number: 76706-55-3
• MDL Number: MFCD00043397
• PubChem SID: 162248859
• PubChem CID: 16219676

CALCULATED PROPERTIES

• Acid pKa: 15.913215
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.9648523
• LogD (pH = 7.4): 4.9648876
• Log P: 4.964888
• Molar Refractivity: 149.9679 cm^3
• Polarizability: 52.86929 Å^3
• Polar Surface Area: 87.33 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble; chloroform: soluble; dichloromethane: soluble; DMSO: soluble; ethanol: soluble; ethyl acetate: soluble; methanol: soluble

Safety Information

• Storage Condition: protect from light; under inert gas
• RTECS: QH7580000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 1
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97.0% (HPLC); ≥98% (HPLC)
• Biological Source: from Myxococcus fulvus Mx f85
• Empirical Formula (Hill Notation): C25H33N3O3S2

DETAILS

Sigma Aldrich - T5580

Biochem/physiol Actions
Myxothiazol, an antibiotic with activity against fungi and insects, is a strong inhibitor of mitochondrial cytochrome b/c1-segment of respiratory chain.1 Myxothiazol binds to the quinol oxidation (Qo) site of the bc1 complex, blocking electron transfer to the Rieske iron-sulfur protein in the mitochondrial respiratory chain.2,3 Oxygen consumption blockage leads to a cytostatic effect that could be reversed. Myxothiazol, as other Epothilones, which are known for their anti tumor activity, contains a thiazole ring that is formed by the incorporation of cysteine into the polyketide backbone.4

Sigma Aldrich - 70183

Biochem/physiol Actions
Strong inhibitor of mitochondrial cytochrome b/c1-segment of respiratory chain. Completely blocks electron transfer from ubiquinone to cytochrome b.1,2 Antibiotic with activity against fungi and insects.3