(1S,2R,10R,11S,14R,15S)-14-acetyl-8-bromo-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-14-yl acetate

• ChemBase ID: 162810
• Molecular Formular: C23H29BrO4
• Molecular Mass: 449.37796
• Monoisotopic Mass: 448.12492141
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](C=C2Br)[C@H]2[C@](CC1)([C@@](CC2)(OC(=O)C)C(=O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C(=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(OC(=O)C)C(=O)C)C)Br)C
• InChI: InChI=1S/C23H29BrO4/c1-13(25)23(28-14(2)26)10-7-18-16-12-20(24)19-11-15(27)5-8-21(19,3)17(16)6-9-22(18,23)4/h11-12,16-18H,5-10H2,1-4H3/t16-,17+,18+,21-,22+,23+/m1/s1
• InChIKey: ZNELXLYMMBIRSK-DFXBJWIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-acetyl-8-bromo-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-14-acetyl-8-bromo-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• Synonyms: 17-(Acetyloxy)-6-bromopregna-4,6-diene-3,20-dione; 6-Bromo-17-hydroxypregna-4,6-diene-3,20-dione Acetate; 6-Bromo-6-dehydro-17α-acetoxy Progesterone

Database IDs

• CAS Number: 15251-04-4
• PubChem SID: 162256945
• PubChem CID: 15516594

CALCULATED PROPERTIES

• Acid pKa: 17.825413
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.881854
• LogD (pH = 7.4): 3.881854
• Log P: 3.881854
• Molar Refractivity: 111.9076 cm^3
• Polarizability: 43.307404 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B682795

Progesterone (P755900) impurity.

REFERENCES

• Liang, T., et al.: Biol. Chem., 256, 7998 (1981)
• Bratoeff, E., et al.: J. Steroid Biochem. Mol. Biol., 111, 275 (1981)