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

• ChemBase ID: 172614
• Molecular Formular: C24H32O4
• Molecular Mass: 384.50848
• Monoisotopic Mass: 384.2300595
• SMILES: [C@@]12(C(=CC(=O)CC2)C(=C[C@@H]2[C@@H]1CC[C@]1([C@H]2CC[C@@]1(C(=O)C)OC(=O)C)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)C)C
• InChI: InChI=1S/C24H32O4/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/h12-13,18-20H,6-11H2,1-5H3/t18-,19+,20+,22-,23+,24+/m1/s1
• InChIKey: RQZAXGRLVPAYTJ-GQFGMJRRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,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]heptadeca-6,8-dien-14-yl acetate
• IUPAC Traditional name: (1S,2R,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]heptadeca-6,8-dien-14-yl acetate
• Synonyms: Magestryl Acetate-d3; Ovarid-d3; Megestrol Acetate-d3; 17-(Acetyloxy)-6-(methyl-d3)-pregna-4,6-diene-3,20-dione; BDH 1298-d3; DMAP-d3; MGA-d3; Magestin-d3; Maygace-d3; Megace-d3; Megeron-d3; Megestat-d3

Database IDs

• PubChem SID: 164228524
• PubChem CID: 71434247

CALCULATED PROPERTIES

• Acid pKa: 17.826162
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.7237444
• LogD (pH = 7.4): 3.7237444
• Log P: 3.7237444
• Molar Refractivity: 108.6554 cm^3
• Polarizability: 42.444622 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow to Pale Green Solid
• Melting Point: 214-216°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M208052

Orally active progestogen; formerly used in combinations as oral contraceptive.

REFERENCES

• Chang, K., et al.: Steroids 12, 689 (1968)