methyl (4R)-4-[(2S,7R,11S,14R,15R,16S)-16-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoate

• ChemBase ID: 173977
• Molecular Formular: C25H40O4
• Molecular Mass: 404.5827
• Monoisotopic Mass: 404.29265976
• SMILES: C1C(=O)C[C@@H]2[C@](C1)(C1C(CC2)[C@H]2[C@]([C@H](C1)O)([C@H](CC2)[C@@H](CCC(=O)OC)C)C)C
• Canonical SMILES: COC(=O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)CC1C2CC[C@H]2[C@]1(C)CCC(=O)C2)C
• InChI: InChI=1S/C25H40O4/c1-15(5-10-23(28)29-4)19-8-9-20-18-7-6-16-13-17(26)11-12-24(16,2)21(18)14-22(27)25(19,20)3/h15-16,18-22,27H,5-14H2,1-4H3/t15-,16-,18?,19-,20+,21?,22+,24+,25-/m1/s1
• InChIKey: LOJPGRHPJBGMMF-VLYSJEDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4R)-4-[(2S,7R,11S,14R,15R,16S)-16-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• IUPAC Traditional name: methyl (4R)-4-[(2S,7R,11S,14R,15R,16S)-16-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• Synonyms: 12-Hydroxy-3-oxo-cholan-24-oic Acid Methyl Ester; Methyl 12α-Hydroxy-3-oxo-5β-cholanate; Methyl-3-keto-12α-hydroxy-5β-cholanoate; Methyl 3-Oxo-desoxycholate

Database IDs

• CAS Number: 10538-58-6
• PubChem SID: 164229887
• PubChem CID: 71750460

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.144654
• LogD (pH = 7.4): 4.1446543
• Log P: 4.1446543
• Molar Refractivity: 112.9378 cm^3
• Polarizability: 45.31572 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol

DETAILS

Toronto Research Chemicals - M321200

Used in the preparation of bile acid-based amino sterols with antimicrobal activity.

REFERENCES

• Li,Q. & Tochtrop,G.; Tetrahedron Lett. 52, 4137 (2011)
• Aher, N. et al.; Bioorg. Med. Chem. Lett. 19, 5411 (2009)