(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyl-13-methylidenetetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-5-one

• ChemBase ID: 128245
• Molecular Formular: C23H30O3
• Molecular Mass: 354.4825
• Monoisotopic Mass: 354.21949482
• SMILES: O=C1C=C2C(=C[C@@H]3[C@H](CC[C@@]4([C@](O)(C(=C)C[C@@H]34)C(=O)C)C)[C@@]2(C)CC1)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C(=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC(=C)[C@]2(O)C(=O)C)C)C)C
• InChI: InChI=1S/C23H30O3/c1-13-10-17-18(21(4)8-6-16(25)12-19(13)21)7-9-22(5)20(17)11-14(2)23(22,26)15(3)24/h10,12,17-18,20,26H,2,6-9,11H2,1,3-5H3/t17-,18+,20+,21-,22+,23+/m1/s1
• InChIKey: OKHAOBQKCCIRLO-IBVJIVQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyl-13-methylidenetetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-5-one
• IUPAC Traditional name: melengestrol
• Synonyms: 17-Hydroxy-6-methyl-16-methylenepregna-4,6-diene-3,20-dione; Melengesterol; Melengestrel; Melengestrol

Database IDs

• CAS Number: 5633-18-1
• PubChem SID: 162222554
• PubChem CID: 9906614
• Chemspider ID: 8082266
• Wikipedia Title: Melengestrol

CALCULATED PROPERTIES

• Acid pKa: 12.214331
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.3778996
• LogD (pH = 7.4): 3.377893
• Log P: 3.3778996
• Molar Refractivity: 103.676 cm^3
• Polarizability: 40.216084 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Yellow Solid
• Melting Point: 188-190°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M215340

Melengestrol Acetate derivative, an orally active progestational steroid.

REFERENCES

• Patton, M., et al.: Zoo Biol., 26, 311(2007)
• Sellin, M., et al.: Environ. Toxicol. Chem., 28, 2443 (2007)
• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2007)
• Sanseverino, J., et al.: Toxicol. Sci., 107, 122 (2007)