(1R,2S,5R,6R,9S,10S,12R,13R,15R)-13-bromo-5-methyl-6-[(2R)-6-methylheptan-2-yl]-19-oxapentacyclo[10.5.2.01,13.02,10.05,9]nonadecan-15-yl acetate

• ChemBase ID: 162883
• Molecular Formular: C29H47BrO3
• Molecular Mass: 523.58568
• Monoisotopic Mass: 522.27085736
• SMILES: C1[C@H](C[C@]2([C@]3(C1)[C@@H]1[C@@H](C[C@@H]2OC3)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CCCC(C)C)C)C)Br)OC(=O)C
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@H]2[C@@]3([C@]1(CO2)CC[C@H](C3)OC(=O)C)Br)C)C
• InChI: InChI=1S/C29H47BrO3/c1-18(2)7-6-8-19(3)23-9-10-24-22-15-26-29(30)16-21(33-20(4)31)11-14-28(29,17-32-26)25(22)12-13-27(23,24)5/h18-19,21-26H,6-17H2,1-5H3/t19-,21-,22+,23-,24+,25+,26-,27-,28+,29+/m1/s1
• InChIKey: YEACHZHDRMYMDK-WJIQIBEWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5R,6R,9S,10S,12R,13R,15R)-13-bromo-5-methyl-6-[(2R)-6-methylheptan-2-yl]-19-oxapentacyclo[10.5.2.0^1,^1^3.0^2,^1^0.0^5,^9]nonadecan-15-yl acetate
• IUPAC Traditional name: (1R,2S,5R,6R,9S,10S,12R,13R,15R)-13-bromo-5-methyl-6-[(2R)-6-methylheptan-2-yl]-19-oxapentacyclo[10.5.2.0^1,^1^3.0^2,^1^0.0^5,^9]nonadecan-15-yl acetate
• Synonyms: (3β,5α,6β)-5-Bromo-6,19-epoxy-cholestan-3-ol Acetate; 5α-Bromo-6,19-oxidocholestanol Acetate; 5α-Bromo-6,19-epoxycholestanol 3-Acetate

Database IDs

• CAS Number: 1258-07-7
• PubChem SID: 162257018
• PubChem CID: 71314244

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 7.073616
• LogD (pH = 7.4): 7.073616
• Log P: 7.073616
• Molar Refractivity: 136.0631 cm^3
• Polarizability: 54.551968 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Cyclohexane; Dichloromethane; Ethyl Acetate; Hexane
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B684285

Intermediate in the chemical synthesis of cholesterol derivatives, and substrate for producing androsterone derivatives via bacterial steroid biotransformation.

REFERENCES

• Hadd, H., et al.: Steroids, 31, 453 (1978)
• Jou, H., et al.: Nuc. Sci. J., 19, 45 (1978)