(1'S,2'R,10'R,11'S,14'S,15'S)-14'-hydroxy-2',15'-dimethylspiro[oxirane-2,8'-tetracyclo[8.7.0.02,7.011,15]heptadecane]-3',6'-dien-5'-one

• ChemBase ID: 175966
• Molecular Formular: C20H26O3
• Molecular Mass: 314.41864
• Monoisotopic Mass: 314.18819469
• SMILES: C1=C[C@]2(C(=CC1=O)C1(C[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2O)C)CO1)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)C1(CO1)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
• InChI: InChI=1S/C20H26O3/c1-18-7-5-12(21)9-16(18)20(11-23-20)10-13-14-3-4-17(22)19(14,2)8-6-15(13)18/h5,7,9,13-15,17,22H,3-4,6,8,10-11H2,1-2H3/t13-,14-,15-,17-,18+,19-,20?/m0/s1
• InChIKey: ODMZYNAXKLSHLW-POJIJWSDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2'R,10'R,11'S,14'S,15'S)-14'-hydroxy-2',15'-dimethylspiro[oxirane-2,8'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-3',6'-dien-5'-one
• IUPAC Traditional name: (1'S,2'R,10'R,11'S,14'S,15'S)-14'-hydroxy-2',15'-dimethylspiro[oxirane-2,8'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-3',6'-dien-5'-one
• Synonyms: (6α,17β)- 17-Hydroxyspiro[androsta-1,4-diene-6,2'-oxiran]-3-one; 17β-Hydroxy-6α-spiro[androsta-1,4-diene-6,2'-oxiran]-3-one; Exemestane Epoxide Metabolite; 6-Oxirane Boldenone(Mixture of Diastereomers)

Database IDs

• PubChem SID: 164231876
• PubChem CID: 71751358

CALCULATED PROPERTIES

• Acid pKa: 19.377705
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.5278058
• LogD (pH = 7.4): 2.527806
• Log P: 2.527806
• Molar Refractivity: 89.7104 cm^3
• Polarizability: 34.82214 Å^3
• Polar Surface Area: 49.83 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O846900

A potential metabolite of Exemestane; also an analog of Boldenone.

REFERENCES

• Buzzetti, F., et al.: Steroids, 58, 527 (1993)