(1R,2S,5S,7R,10R,11S,14R,15S)-15-ethyl-14-ethynyltetracyclo[8.7.0.02,7.011,15]heptadecane-5,14-diol

• ChemBase ID: 178394
• Molecular Formular: C21H32O2
• Molecular Mass: 316.47758
• Monoisotopic Mass: 316.24023026
• SMILES: C1[C@@H](C[C@@H]2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@@](CC1)(CC)[C@](CC2)(O)C#C)O
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(CC)CC[C@H]1[C@H]2CC[C@H]2[C@@H]1CC[C@@H](C2)O
• InChI: InChI=1S/C21H32O2/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/h2,14-19,22-23H,3,5-13H2,1H3/t14-,15+,16+,17-,18-,19+,20+,21+/m1/s1
• InChIKey: PTHVTSMKEGKAHY-ZENBKHFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5S,7R,10R,11S,14R,15S)-15-ethyl-14-ethynyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-diol
• IUPAC Traditional name: (1R,2S,5S,7R,10R,11S,14R,15S)-15-ethyl-14-ethynyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-diol
• Synonyms: 13-Ethyl-18,19-dinor-5β,17α-pregn-20-yne-3β,17-diol; 3β,5β-Tetrahydro Norgestrel

Database IDs

• CAS Number: 19351-17-8
• PubChem SID: 164234304
• PubChem CID: 71752467

CALCULATED PROPERTIES

• Acid pKa: 17.90929
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.50013
• LogD (pH = 7.4): 3.5001302
• Log P: 3.5001302
• Molar Refractivity: 92.2269 cm^3
• Polarizability: 36.63463 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - T294155

Norgestrel (N689500) metabolite.

REFERENCES

• Khan, F. S. et al.; J. Steroid Biochem. 19, 1169 (1983)
• Uniyal, J. P. et al.; Acta Endrocrinol. 84, 155 (1977)