(1S,2R,10R,11S,14S,15S)-14-(cyclopent-1-en-1-yloxy)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 177275
• Molecular Formular: C24H32O2
• Molecular Mass: 352.50968
• Monoisotopic Mass: 352.24023026
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2OC1=CCCC1)C)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2OC1=CCCC1)C)C
• InChI: InChI=1S/C24H32O2/c1-23-13-11-17(25)15-16(23)7-8-19-20-9-10-22(26-18-5-3-4-6-18)24(20,2)14-12-21(19)23/h5,11,13,15,19-22H,3-4,6-10,12,14H2,1-2H3/t19-,20-,21-,22-,23-,24-/m0/s1
• InChIKey: IUVKMZGDUIUOCP-BTNSXGMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14S,15S)-14-(cyclopent-1-en-1-yloxy)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: quinbolone
• Synonyms: (17β)-17-(1-Cyclopenten-1-yloxy)androsta-1,4-dien-3-one; 17β-(1-Cyclopenten-1-yloxy)androsta-1,4-dien-3-one; Anabolicum Vister; Anabolvis; Quindenione; Quinbolone

Database IDs

• CAS Number: 2487-63-0
• PubChem SID: 164233185
• PubChem CID: 10360683

CALCULATED PROPERTIES

• Acid pKa: 18.863604
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.0288186
• LogD (pH = 7.4): 5.0288186
• Log P: 5.0288186
• Molar Refractivity: 108.1809 cm^3
• Polarizability: 41.344257 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - Q670150

Quinbolone is an anabolic steroid. Quinbolone is a cyclopentenyl ether derivative of Boldenone (B675100) which is also its active metabolite. Quinbolone shows weak androgenic activity.

REFERENCES

• Balestreri, R. et al.: Arch. Maragl. Patol. Clin., 22, 369 (1966)
• Galletti, F. et al.: Steroids, 18, 39 (1966)