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

• ChemBase ID: 128645
• Molecular Formular: C23H30O4
• Molecular Mass: 370.4819
• Monoisotopic Mass: 370.21440944
• SMILES: O=C1C=C2C(=C[C@@H]3[C@H](CC[C@@]4([C@@](OC(=O)C)(C(=O)C)CC[C@@H]34)C)[C@H]2CC1)C
• Canonical SMILES: CC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C=C(C2=CC(=O)CC[C@H]12)C)C(=O)C
• InChI: InChI=1S/C23H30O4/c1-13-11-20-18(17-6-5-16(26)12-19(13)17)7-9-22(4)21(20)8-10-23(22,14(2)24)27-15(3)25/h11-12,17-18,20-21H,5-10H2,1-4H3/t17-,18-,20-,21+,22+,23+/m1/s1
• InChIKey: IIVBFTNIGYRNQY-YQLZSBIMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S)-14-acetyl-8,15-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,10S,11S,14R,15S)-14-acetyl-8,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• Synonyms: Nomegestrol acetate; 17-(Acetyloxy)-6-methyl-19-norpregna-4,6-diene-3,20-dione; 6-Methyl-17.alpha.-acetoxy-6-19-norprogesterone; Lutenyl; Surplant; TX 066; Uniplant

Database IDs

• CAS Number: 58652-20-3; 85652-20-3
• PubChem SID: 162222952
• PubChem CID: 91668
• ATC CODE: G03DB04
• Chemspider ID: 82771
• Wikipedia Title: Nomegestrol_acetate

CALCULATED PROPERTIES

• Acid pKa: 17.82221
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.4236972
• LogD (pH = 7.4): 3.4236972
• Log P: 3.4236972
• Molar Refractivity: 104.1803 cm^3
• Polarizability: 40.604465 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Rx-only

DETAILS

Toronto Research Chemicals - N635855

Progetin used in implantable hormone replacement therapies.

REFERENCES

• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2009)
• Vukusic, S., et al.: J. Neurol. Sci., 286, 114 (2009)
• Barbosa, I., et al.: Gynecol., Endocrinol., 25, 269 (2009)