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

• ChemBase ID: 170769
• Molecular Formular: C20H26O3
• Molecular Mass: 314.41864
• Monoisotopic Mass: 314.18819469
• SMILES: C1=C[C@]2(C(=CC1=O)[C@@H](C[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)CO)C
• Canonical SMILES: OC[C@@H]1C[C@@H]2[C@@H]([C@@]3(C1=CC(=O)C=C3)C)CC[C@]1([C@H]2CCC1=O)C
• InChI: InChI=1S/C20H26O3/c1-19-7-5-13(22)10-17(19)12(11-21)9-14-15-3-4-18(23)20(15,2)8-6-16(14)19/h5,7,10,12,14-16,21H,3-4,6,8-9,11H2,1-2H3/t12-,14-,15-,16-,19+,20-/m0/s1
• InChIKey: DAXJNUBSBFUTRP-JKNDIDBPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8R,10R,11S,15S)-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,8R,10R,11S,15S)-8-(hydroxymethyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,14-dione
• Synonyms: 6β-(Hydroxymethyl)androsta-1,4-dien-3,17-dione; 6β-Hydroxymethylandrosta-1,4-diene-3,17-dione

Database IDs

• CAS Number: 121021-51-0
• PubChem SID: 164226679
• PubChem CID: 11842920

CALCULATED PROPERTIES

• Acid pKa: 17.68266
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.8550687
• LogD (pH = 7.4): 2.8550687
• Log P: 2.8550687
• Molar Refractivity: 91.1011 cm^3
• Polarizability: 34.930843 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H946395

6β-Hydroxymethylandrosta-1,4-diene-3,17-dione is a derivative of Exemestane (E957000) and a potential aromatase inhibitor.

REFERENCES

• Goerlitzer, K. et al.: Pharmazie, 61, 575 (2006)
• Goerlitzer, K. et al.: Deut. Apoth. Zeit., 145, 69 (2006)