(1S,2R,10R,11S,15S)-8-hydroxy-8-(hydroxymethyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-5,14-dione

• ChemBase ID: 170655
• Molecular Formular: C20H26O4
• Molecular Mass: 330.41804
• Monoisotopic Mass: 330.18310931
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2(CO)O)[C@H]2[C@](CC1)(C(=O)CC2)C)C
• Canonical SMILES: OCC1(O)C[C@@H]2[C@@H]([C@@]3(C1=CC(=O)C=C3)C)CC[C@]1([C@H]2CCC1=O)C
• InChI: InChI=1S/C20H26O4/c1-18-7-5-12(22)9-16(18)20(24,11-21)10-13-14-3-4-17(23)19(14,2)8-6-15(13)18/h5,7,9,13-15,21,24H,3-4,6,8,10-11H2,1-2H3/t13-,14-,15-,18+,19-,20?/m0/s1
• InChIKey: NQQZWPXWZWALLC-YCNUYBHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,15S)-8-hydroxy-8-(hydroxymethyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,14-dione
• IUPAC Traditional name: (1S,2R,10R,11S,15S)-8-hydroxy-8-(hydroxymethyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,14-dione
• Synonyms: FCE 27473; 6-Hydroxy-6-(hydroxymethyl)-androsta-1,4-diene-3,17-dione(Mixture of Diastereomers)

Database IDs

• CAS Number: 184972-11-0
• PubChem SID: 164226565
• PubChem CID: 71749075

CALCULATED PROPERTIES

• Acid pKa: 13.332757
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.9296302
• LogD (pH = 7.4): 1.9296296
• Log P: 1.9296302
• Molar Refractivity: 92.3982 cm^3
• Polarizability: 35.56064 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Tetrahydrofuran
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - H943105

A metabolite of Exemestane (E957000) in human body fluids.

REFERENCES

• Persiani, S. et al.: Eur. J. Pharm. Sci., 4, 331 (1996)