(1S,2S,14S,15R)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-6,8,10-trien-5-one

• ChemBase ID: 176899
• Molecular Formular: C21H26O2
• Molecular Mass: 310.42994
• Monoisotopic Mass: 310.19328007
• SMILES: C1C(=O)C=C2[C@@](C1)([C@H]1C(=C3[C@](CC1)([C@H](CC3)C(=O)C)C)C=C2)C
• Canonical SMILES: O=C1CC[C@@]2(C(=C1)C=CC1=C3[C@@](CC[C@@H]21)(C)[C@H](CC3)C(=O)C)C
• InChI: InChI=1S/C21H26O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,12,17,19H,6-11H2,1-3H3/t17-,19-,20-,21-/m1/s1
• InChIKey: HMDYHHQZKIYROJ-CWJKEVGVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,14S,15R)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8,10-trien-5-one
• IUPAC Traditional name: (1S,2S,14S,15R)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8,10-trien-5-one
• Synonyms: 9β,10α-Pregna-4,6,8(14)-triene-3,20-dione

Database IDs

• CAS Number: 23035-53-2
• PubChem SID: 164232809
• PubChem CID: 71587052

CALCULATED PROPERTIES

• Acid pKa: 19.243666
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.3374455
• LogD (pH = 7.4): 3.3374455
• Log P: 3.3374455
• Molar Refractivity: 94.4053 cm^3
• Polarizability: 35.92145 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P711600

9β,10α-Pregna-4,6,8(14)-triene-3,20-dione is a 3-keto steroid with fluorescent properties that make it useful as a probe for steroid-protein interactions. Also an impurity found in dydrogesterone (D826000).

REFERENCES

• Kempfle, M. et al.: Eur. Biophys. J., 14, 29 (1986)