(1R,2R,14R,15R)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.02,7.011,15]heptadeca-6,10-dien-5-one

• ChemBase ID: 165666
• Molecular Formular: C21H26O2
• Molecular Mass: 310.42994
• Monoisotopic Mass: 310.19328007
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1C(=C3[C@@](CC1)([C@](CC3)(O)C#C)CC)CC2
• Canonical SMILES: CC[C@@]12CC[C@H]3C(=C1CC[C@@]2(O)C#C)CCC1=CC(=O)CC[C@H]31
• InChI: InChI=1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-17,23H,3,5-12H2,1H3/t16-,17+,20+,21-/m0/s1
• InChIKey: PIGNQOCLJHWTGZ-NLEAXPPASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,14R,15R)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,10-dien-5-one
• IUPAC Traditional name: (1R,2R,14R,15R)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,10-dien-5-one
• Synonyms: (+/-)-(17α)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,8(14)-dien-20-yn-3-one; 8(14)-Dehydro Norgestrel

Database IDs

• CAS Number: 110785-09-6
• PubChem SID: 162259799
• PubChem CID: 71315326

CALCULATED PROPERTIES

• Polarizability: 35.607704 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 17.804922
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.2125592
• LogD (pH = 7.4): 3.2125592
• Log P: 3.2125592
• Molar Refractivity: 92.6089 cm^3

DETAILS

Toronto Research Chemicals - D229925

Norgestrel (N689500) impurity.

REFERENCES

• Gorog, S., et al.: J. Chromatogr., 400 177 (1987)