[(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl]oxidanesulfonic acid

• ChemBase ID: 175656
• Molecular Formular: C21H28O5S
• Molecular Mass: 392.50902
• Monoisotopic Mass: 392.165745
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@@](CC2)(C#C)OS(=O)(=O)O)CC
• Canonical SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)OS(=O)(=O)O)CCC1=CC(=O)CC[C@H]31
• InChI: InChI=1S/C21H28O5S/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,4-2)26-27(23,24)25/h2,13,16-19H,3,5-12H2,1H3,(H,23,24,25)/t16-,17+,18+,19-,20-,21-/m0/s1
• InChIKey: LFTOQTVKUXTEIN-XUDSTZEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]oxidanesulfonic acid
• IUPAC Traditional name: [(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]oxidanesulfonic acid
• Synonyms: Levonorgestrel Sulfate; D-(-)-Norgestrel-17-sulfate; D-(-)-Norgestrel Sulfate

Database IDs

• PubChem SID: 164231566
• PubChem CID: 29985987

CALCULATED PROPERTIES

• Acid pKa: -1.3488442
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.3403982
• LogD (pH = 7.4): 1.3403838
• Log P: 3.7167823
• Molar Refractivity: 102.0173 cm^3
• Polarizability: 40.57508 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N689520

A metabolite of Norgestrel.