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

• ChemBase ID: 119294
• Molecular Formular: C23H30O4
• Molecular Mass: 370.4819
• Monoisotopic Mass: 370.21440944
• SMILES: [C@]12([C@@](CC[C@H]1[C@H]1[C@@H]([C@@]3(C(=CC(=O)CC3)C=C1)C)CC2)(OC(=O)C)C(=O)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
• InChI: InChI=1S/C23H30O4/c1-14(24)23(27-15(2)25)12-9-20-18-6-5-16-13-17(26)7-10-21(16,3)19(18)8-11-22(20,23)4/h5-6,13,18-20H,7-12H2,1-4H3/t18-,19+,20+,21+,22+,23+/m1/s1
• InChIKey: URXWVWVPMJSAJD-KOORYGTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-acetyl-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: megestat
• Synonyms: (8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate; 17-(Acetyloxy)pregna-4,6-diene-3,20-dione; 17-Hydroxypregna-4,6-diene-3,20-dione Acetate; 17α-Acetoxypregna-4,6-diene-3,20-dione; 17α-Hydroxy-6-dehydroprogesterone Acetate; Melengestro Acetate; NSC 77897; Pregna-4,6-dien-17-ol-3,20-dione Acetate; Δ6-Dehydro-17α-acetoxyprogesterone; 6,7-Dehydro-17α-acetoxy Progesterone

Database IDs

• CAS Number: 425-51-4
• PubChem SID: 162107481
• PubChem CID: 200136

CALCULATED PROPERTIES

• Acid pKa: 17.826315
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.480383
• LogD (pH = 7.4): 3.480383
• Log P: 3.480383
• Molar Refractivity: 104.3734 cm^3
• Polarizability: 40.604465 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Toronto Research Chemicals - D229090

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)