(1S,2R,10R,11S,15S)-5-methoxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-5,7-dien-14-one

• ChemBase ID: 172728
• Molecular Formular: C20H28O2
• Molecular Mass: 300.43512
• Monoisotopic Mass: 300.20893014
• SMILES: C1C(=CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CCC1=O)C)OC
• Canonical SMILES: COC1=CC2=CC[C@@H]3[C@@H]([C@]2(CC1)C)CC[C@]1([C@H]3CCC1=O)C
• InChI: InChI=1S/C20H28O2/c1-19-10-8-14(22-3)12-13(19)4-5-15-16-6-7-18(21)20(16,2)11-9-17(15)19/h4,12,15-17H,5-11H2,1-3H3/t15-,16-,17-,19-,20-/m0/s1
• InChIKey: WSIQEGIPGPEMTC-TXTPUJOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,15S)-5-methoxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-5,7-dien-14-one
• IUPAC Traditional name: (1S,2R,10R,11S,15S)-5-methoxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-5,7-dien-14-one
• Synonyms: 3-Methoxyandrosta-3,5-dien-17-one; 3-Methoxy Androsta-3,5-dien-17-one

Database IDs

• CAS Number: 57144-06-6
• PubChem SID: 164228638
• PubChem CID: 92687

CALCULATED PROPERTIES

• Acid pKa: 19.9577
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.672575
• LogD (pH = 7.4): 3.672575
• Log P: 3.672575
• Molar Refractivity: 90.9035 cm^3
• Polarizability: 34.93832 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M226040

An intermediate used in the synthesis of Drospirenone (D689500) from Androstenedione (A637550).

REFERENCES

• Potter, G., et al.: J. Med. Chem., 38, 2463 (1995)
• Skoda-Foldes, R., et al.: Steroids, 67, 709 (1995)