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

• ChemBase ID: 175652
• Molecular Formular: C23H32O4
• Molecular Mass: 372.49778
• Monoisotopic Mass: 372.2300595
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1C)([C@@](CC2)(OC(=O)C)C(=O)C)C
• Canonical SMILES: CC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)C[C@H](C)[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12)C(=O)C
• InChI: InChI=1S/C23H32O4/c1-13-12-22(4)20(9-10-23(22,14(2)24)27-15(3)25)19-7-5-16-11-17(26)6-8-18(16)21(13)19/h11,13,18-21H,5-10,12H2,1-4H3/t13-,18-,19-,20-,21+,22-,23-/m0/s1
• InChIKey: IWSXBCZCPVUWHT-VIFKTUCRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S,17S)-14-acetyl-15,17-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: norgestomet
• Synonyms: (11β)-17-(Acetyloxy)-11-methyl-19-norpregn-4-ene-3,20-dione; 17α-Acetoxy-11β-methyl-19-norpregn-4-ene-3,20-dione; Crestar; Norgestomet; SC 21009; Norprogesterone

Database IDs

• CAS Number: 25092-41-5
• PubChem SID: 164231562
• PubChem CID: 9820838

CALCULATED PROPERTIES

• Acid pKa: 17.810751
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.8292766
• LogD (pH = 7.4): 3.8292766
• Log P: 3.8292766
• Molar Refractivity: 103.3303 cm^3
• Polarizability: 40.84742 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N686500

A progesterone analogue (mammalian hormones).

REFERENCES

• Kaneko, H., et al.: Biol. Reprod., 53, 931 (1995)
• Brown, M., et al.: J. Anim. Sci., 80, 2522 (1995)