(1S,2R,10R,11S,13S,14R,15S)-15-ethyl-14-ethynyl-13,14-dihydroxytetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 171005
• Molecular Formular: C21H28O3
• Molecular Mass: 328.44522
• Monoisotopic Mass: 328.20384476
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@@](CC1)(CC)[C@]([C@H](C2)O)(O)C#C
• Canonical SMILES: C#C[C@]1(O)[C@@H](O)C[C@@H]2[C@]1(CC)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
• InChI: InChI=1S/C21H28O3/c1-3-20-10-9-16-15-8-6-14(22)11-13(15)5-7-17(16)18(20)12-19(23)21(20,24)4-2/h2,11,15-19,23-24H,3,5-10,12H2,1H3/t15-,16+,17+,18-,19-,20-,21-/m0/s1
• InChIKey: CPLFYDXNDVOJDT-SVMVYQPLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,13S,14R,15S)-15-ethyl-14-ethynyl-13,14-dihydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,13S,14R,15S)-15-ethyl-14-ethynyl-13,14-dihydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (16β,17α)- 13-ethyl-16,17-dihydroxy-18,19-Dinorpregn-4-en-20-yn-3-one; 16β-Hydroxynorgestrel; 16β-Hydroxy Norgestrel

Database IDs

• CAS Number: 40915-03-5
• PubChem SID: 164226915
• PubChem CID: 21125717

CALCULATED PROPERTIES

• Acid pKa: 12.004877
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.5868928
• LogD (pH = 7.4): 2.586882
• Log P: 2.586893
• Molar Refractivity: 93.387 cm^3
• Polarizability: 36.46381 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948795

A metabolite of the progestational agent Norgestrel (N689500).

REFERENCES

• Sisenwine, S.F. et al.: Acta Endocrinol., 73, 91 (1973)
• Sisenwine, S.F. et al.: Drug Metab. Disp., 7, 1 (1973)