(1S,2R,4R,5S,7S,10S,11S,14R,15S)-14-[(2S,3R,4R,5R)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-4,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-8-one

• ChemBase ID: 163861
• Molecular Formular: C28H48O5
• Molecular Mass: 464.67772
• Monoisotopic Mass: 464.35017464
• SMILES: [C@@H]1([C@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2=O)[C@H]2[C@](CC1)([C@H](CC2)[C@@H]([C@H]([C@@H]([C@@H](C(C)C)C)O)O)C)C)C)O)O
• Canonical SMILES: O[C@H]([C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC(=O)[C@@H]2[C@]1(C)C[C@@H](O)[C@H](C2)O)C)[C@@H]([C@@H](C(C)C)C)O
• InChI: InChI=1S/C28H48O5/c1-14(2)15(3)25(32)26(33)16(4)18-7-8-19-17-11-22(29)21-12-23(30)24(31)13-28(21,6)20(17)9-10-27(18,19)5/h14-21,23-26,30-33H,7-13H2,1-6H3/t15-,16+,17+,18-,19+,20+,21-,23+,24-,25-,26-,27-,28-/m1/s1
• InChIKey: VYUIKSFYFRVQLF-QONPFPPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4R,5S,7S,10S,11S,14R,15S)-14-[(2S,3R,4R,5R)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-4,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-8-one
• IUPAC Traditional name: (1S,2R,4R,5S,7S,10S,11S,14R,15S)-14-[(2S,3R,4R,5R)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-4,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-8-one
• Synonyms: (2α,3α,5α,22R,23R)-2,3,22,23-Tetrahydroxyergostan-6-one; 24-Epicastasterone; 24R-Epicastasterone; 24-epi-Castasterone

Database IDs

• CAS Number: 72050-71-6
• PubChem SID: 162257996
• PubChem CID: 11812633

CALCULATED PROPERTIES

• Acid pKa: 13.454505
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.5016189
• LogD (pH = 7.4): 3.5016184
• Log P: 3.5016189
• Molar Refractivity: 129.2209 cm^3
• Polarizability: 51.937244 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C226490

A metabolite of Castasterone (C226500). An 24-epimer of Castasterone.

REFERENCES

• Greenwood, D., et al.: Biochem. J., 217, 783 (1984)
• Fujimoto, Y., et al.: Steroids, 53, 477 (1984)