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

• ChemBase ID: 170235
• Molecular Formular: C21H28O3
• Molecular Mass: 328.44522
• Monoisotopic Mass: 328.20384476
• SMILES: C1C(=O)C=C2[C@](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]2CCC2=CC(=O)CC[C@]12O
• InChI: InChI=1S/C21H28O3/c1-3-19-10-8-18-16(17(19)9-11-20(19,23)4-2)6-5-14-13-15(22)7-12-21(14,18)24/h2,13,16-18,23-24H,3,5-12H2,1H3/t16-,17-,18-,19-,20-,21+/m0/s1
• InChIKey: ZMTZYQYDIREIIA-HXIANDDZSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 21508-50-9
• PubChem SID: 164226145
• PubChem CID: 71748888

CALCULATED PROPERTIES

• Acid pKa: 13.935827
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.5804505
• LogD (pH = 7.4): 2.5804505
• Log P: 2.5804505
• Molar Refractivity: 93.4766 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 - H825710

10β-Hydroxy D-(-)-Norgestrel is an impurity of Levonorgestrel (N689510).

REFERENCES

• Gorog, S. et al.: J. Pharmac. Biomed. Anal., 14, 85 (1995)
• Berta, R. et al.: J. Pharmac. Biomed. Anal., 54, 458 (1995)
• Choudhary, M. I. et al.: Nat. Prod. Res., 20, 1074 (1995)