(1S,2R,8S,10R,11S,14R,15S)-14-acetyl-8-(2H3)methyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl acetate

• ChemBase ID: 172607
• Molecular Formular: C24H34O4
• Molecular Mass: 386.52436
• Monoisotopic Mass: 386.24570957
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](C[C@@H]2C)[C@H]2[C@](CC1)([C@](CC2)(C(=O)C)OC(=O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(OC(=O)C)C(=O)C)C)C
• InChI: InChI=1S/C24H34O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h13-14,18-20H,6-12H2,1-5H3/t14-,18+,19-,20-,22+,23-,24-/m0/s1
• InChIKey: PSGAAPLEWMOORI-PEINSRQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10R,11S,14R,15S)-14-acetyl-8-(^2H₃)methyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: (1S,2R,8S,10R,11S,14R,15S)-14-acetyl-8-(^2H₃)methyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• Synonyms: (6β)-17-(Acetyloxy)-6-(methyl-d3)pregn-4-ene-3,20-dione; 17-Hydroxy-6β-(methyl-d3)pregn-4-ene-3,20-dione Acetate; 17-Hydroxy-6β-(methyl-d3)progesterone Acetate; 6β-(Methyl-d3)-17α-hydroxyprogesterone Acetate; NSC 119085-d3; epi-Medroxy Progesterone-d3 17-Acetate

Database IDs

• PubChem SID: 164228517
• PubChem CID: 71749937

CALCULATED PROPERTIES

• Acid pKa: 17.821218
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.129324
• LogD (pH = 7.4): 4.129324
• Log P: 4.129324
• Molar Refractivity: 107.8054 cm^3
• Polarizability: 42.687153 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M203572

The labelled epimer of Medroxyprogesterone acetate (M203560). Progesterone impurity.

REFERENCES

• Tang, M., et al.: Endocrinol., 151, 1320 (2010)
• Lee, K., et al.: Mol. Cell. Endocrinol., 319, 109 (2010)
• Rodgers, A., et al.: Chem., Res. Toxicol., 23, 724 (2010)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)