(1R,2S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl acetate

• ChemBase ID: 169053
• Molecular Formular: C23H31FO5
• Molecular Mass: 406.4876432
• Monoisotopic Mass: 406.21555231
• SMILES: C1C(=O)C=C2[C@](C1)([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@@](CC2)(OC(=O)C)C(=O)C)C)F)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1CC[C@]2(OC(=O)C)C(=O)C)C)C
• InChI: InChI=1S/C23H31FO5/c1-13(25)22(29-14(2)26)10-8-17-18-6-5-15-11-16(27)7-9-20(15,3)23(18,24)19(28)12-21(17,22)4/h11,17-19,28H,5-10,12H2,1-4H3/t17-,18-,19-,20-,21-,22-,23-/m0/s1
• InChIKey: JKQQZJHNUVDHKP-FQJIPJFPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: fluorogestone acetate
• Synonyms: (11β)-17-(Acetyloxy)-9-fluoro-11-hydroxy-pregn-4-ene-3,20-dione; 17α-Acetoxy-9α-fluoro-11β-hydroxy-pregn-4-ene-3,20-dione; 17α-Acetoxy-9α-fluoro-11β-hydroxyprogesterone; Gyncro-Mate; NSC 65411; Flugestone 17-Acetate

Database IDs

• CAS Number: 2529-45-5
• PubChem SID: 162263185
• PubChem CID: 10476437

CALCULATED PROPERTIES

• Acid pKa: 13.651136
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.5771468
• LogD (pH = 7.4): 2.5771465
• Log P: 2.5771468
• Molar Refractivity: 104.3773 cm^3
• Polarizability: 41.226315 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - F489650

A synthetic progesterone, used to induce oestrus synchronisation in goats and sheep.

REFERENCES

• Mei, C., et al.: Reproduct. Dom. An., 44, 735 (2009)
• Letelier, C., et al.: Theriogenol., 71 676 (2009)
• Letelier, C., et al.: Fertil. Steril., 93, 1308 (2009)