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

• ChemBase ID: 128646
• Molecular Formular: C21H28O3
• Molecular Mass: 328.44522
• Monoisotopic Mass: 328.20384476
• SMILES: O=C1C=C2C(=C[C@@H]3[C@H](CC[C@@]4([C@@](O)(C(=O)C)CC[C@@H]34)C)[C@H]2CC1)C
• Canonical SMILES: O=C1CC[C@H]2C(=C1)C(=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C
• InChI: InChI=1S/C21H28O3/c1-12-10-18-16(15-5-4-14(23)11-17(12)15)6-8-20(3)19(18)7-9-21(20,24)13(2)22/h10-11,15-16,18-19,24H,4-9H2,1-3H3/t15-,16-,18-,19+,20+,21+/m1/s1
• InChIKey: KZUIYQJTUIACIG-YBZCJVABSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S)-14-acetyl-14-hydroxy-8,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-5-one
• IUPAC Traditional name: nomegestrol
• Synonyms: 17-Hydroxy-6-methyl-19-norpregna-4,6-diene-3,20-dione; Monaco; Thermex; Nomegestrol

Database IDs

• CAS Number: 58691-88-6
• PubChem SID: 162222953
• PubChem CID: 68783
• ATC CODE: G03DB04
• Chemspider ID: 62024
• Wikipedia Title: Nomegestrol

CALCULATED PROPERTIES

• Acid pKa: 12.699101
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.9825718
• LogD (pH = 7.4): 2.9825697
• Log P: 2.9825718
• Molar Refractivity: 95.0288 cm^3
• Polarizability: 36.772232 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N635850

A progestogen, derivatives of which are used in contraceptives and hormone therapies.

REFERENCES

• Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)
• Catalano, D., et al.: Climacter., 11, 373 (2008)
• Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)