(1S,2S,5R,7S,10S,11S,14S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-17-one

• ChemBase ID: 159733
• Molecular Formular: C21H32O4
• Molecular Mass: 348.47638
• Monoisotopic Mass: 348.2300595
• SMILES: C1[C@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1=O)([C@H](CC2)C(=O)CO)C)C)O
• Canonical SMILES: OCC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CC[C@@H]2[C@]1(C)CC[C@H](C2)O
• InChI: InChI=1S/C21H32O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-16,19,22-23H,3-11H2,1-2H3/t12-,13+,14-,15-,16+,19+,20-,21-/m0/s1
• InChIKey: XWYBFXIUISNTQG-VKMGZQQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7S,10S,11S,14S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-17-one
• IUPAC Traditional name: alfadolone
• Synonyms: (3α,5α)-3,21-Dihydroxypregnane-11,20-dione; 3α,21-Dihydroxy-5α-pregnane-11,20-dione; Alfadolone; Alphadolone

Database IDs

• CAS Number: 14107-37-0
• PubChem SID: 162253868
• PubChem CID: 9798416

CALCULATED PROPERTIES

• Acid pKa: 13.864709
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.2464395
• LogD (pH = 7.4): 2.2464392
• Log P: 2.2464395
• Molar Refractivity: 95.2762 cm^3
• Polarizability: 37.886864 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A575510

Alphadolone or Alfadolone (INN) is a neuroactive steroid with hypnotic effects. Alphadolone is one of the components of Althesin.

REFERENCES

• Harrison, N., et al.: J. Pharmacol. Exp. Ther., 241, 346 (1987)
• Serrao, J., et al.: Anesthesiology, 70, 780 (1987)
• Mistry, D., et al.: Exp. Physiol., 75, 199 (1987)