methyl (1S,2S,10S,11S,15S)-15-methyl-5,14-dioxotetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-2-carboxylate

• ChemBase ID: 173581
• Molecular Formular: C20H26O4
• Molecular Mass: 330.41804
• Monoisotopic Mass: 330.18310931
• SMILES: C1CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C
• InChI: InChI=1S/C20H26O4/c1-19-9-8-16-14(15(19)5-6-17(19)22)4-3-12-11-13(21)7-10-20(12,16)18(23)24-2/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,19-,20+/m0/s1
• InChIKey: IINHZOYCZYVJRR-IEYYFSCXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,2S,10S,11S,15S)-15-methyl-5,14-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-2-carboxylate
• IUPAC Traditional name: methyl (1S,2S,10S,11S,15S)-15-methyl-5,14-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-2-carboxylate
• Synonyms: 3,17-Dioxo-androst-4-en-19-oic Acid Methyl Ester; Methyl 3,17-Dioxo-4-androsten-19-oate

Database IDs

• CAS Number: 22256-03-7
• PubChem SID: 164229491
• PubChem CID: 14409284

CALCULATED PROPERTIES

• Acid pKa: 17.871735
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.2665377
• LogD (pH = 7.4): 3.2665377
• Log P: 3.2665377
• Molar Refractivity: 90.0938 cm^3
• Polarizability: 35.33216 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Tetrahydrofuran
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - M303630

A methoxy hydroperoxide androstenedione derivative; analog of a potential aromatase intermediate.

REFERENCES

• Dyer, R., et al.: Steroids, 33, 617 (1979)