(3S,7S,8S,12Z,15S,16E)-3,7,15-tris[(tert-butyldimethylsilyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

• ChemBase ID: 179024
• Molecular Formular: C45H85NO6SSi3
• Molecular Mass: 852.481
• Monoisotopic Mass: 851.54054004
• SMILES: C(=C\C[C@@H](/C(=C/c1csc(n1)C)/C)O[Si](C(C)(C)C)(C)C)(\CCC[C@@H]([C@@H](C(C(=O)C([C@H](CC(=O)O)O[Si](C(C)(C)C)(C)C)(C)C)C)O[Si](C(C)(C)C)(C)C)C)/C
• Canonical SMILES: C/C(=C/C[C@@H](/C(=C/c1csc(n1)C)/C)O[Si](C(C)(C)C)(C)C)/CCC[C@@H]([C@@H](C(C(=O)C([C@@H](O[Si](C(C)(C)C)(C)C)CC(=O)O)(C)C)C)O[Si](C(C)(C)C)(C)C)C
• InChI: InChI=1S/C45H85NO6SSi3/c1-31(26-27-37(50-54(17,18)42(6,7)8)33(3)28-36-30-53-35(5)46-36)24-23-25-32(2)40(52-56(21,22)44(12,13)14)34(4)41(49)45(15,16)38(29-39(47)48)51-55(19,20)43(9,10)11/h26,28,30,32,34,37-38,40H,23-25,27,29H2,1-22H3,(H,47,48)/b31-26-,33-28+/t32-,34?,37-,38-,40-/m0/s1
• InChIKey: GWEYNQSYTRXNRT-PKRZIIFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7S,8S,12Z,15S,16E)-3,7,15-tris[(tert-butyldimethylsilyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid
• IUPAC Traditional name: (3S,7S,8S,12Z,15S,16E)-3,7,15-tris[(tert-butyldimethylsilyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid
• Synonyms: (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-Tris-{[tert-butyl(dimethyl)silyl]oxy}-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic Acid

Database IDs

• CAS Number: 193146-63-3
• PubChem SID: 164234934
• PubChem CID: 71752741

CALCULATED PROPERTIES

• Acid pKa: 4.24323
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 11.710229
• LogD (pH = 7.4): 9.948417
• Log P: 12.794597
• Molar Refractivity: 229.0796 cm^3
• Polarizability: 96.413246 Å^3
• Polar Surface Area: 94.95 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethanol; Ethyl Acetate
• Apperance: Off-White Sticky Foam

DETAILS

Toronto Research Chemicals - T876500

An intermediate in the synthesis of Epothilones. Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical

REFERENCES

• Hoee, G., et al.: Pure Appl. Chem., 71, 11, 2019 (1999)
• Giannakakou, P., et al.: Proc. Natl. Acad. Sci. USA, 97, 2904 (2000)