(1S,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.02,7.011,15]heptadec-2(7)-en-5-one

• ChemBase ID: 168599
• Molecular Formular: C21H28O2
• Molecular Mass: 312.44582
• Monoisotopic Mass: 312.20893014
• SMILES: C1C(=O)CC2=C(C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)CC
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(CC)CC[C@H]1[C@H]2CCC2=C1CCC(=O)C2
• InChI: InChI=1S/C21H28O2/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/h2,17-19,23H,3,5-13H2,1H3/t17-,18-,19+,20+,21+/m1/s1
• InChIKey: QCMLVDXPKCBMFQ-MJCUULBUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-en-5-one
• IUPAC Traditional name: (1S,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-en-5-one
• Synonyms: 13-Ethyl-17α-ethynyl-17-hydroxygon-5(10)-en-3-one; EP Levonorgestrel Impurity B; (17α)-13-Ethyl-17-hydroxy-18,19-dinorpregn-5(10)-en-20-yn-3-one; 13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-5(10)-en-20-yn-3-one(Levo Norgestrel Impurity)

Database IDs

• CAS Number: 19914-67-1
• PubChem SID: 162262731
• PubChem CID: 29979902

CALCULATED PROPERTIES

• Acid pKa: 16.301239
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.2583935
• LogD (pH = 7.4): 3.2583935
• Log P: 3.2583935
• Molar Refractivity: 91.7822 cm^3
• Polarizability: 35.84699 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 169-171°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E918935

EP Levonorgestrel impurity B.

REFERENCES

• McGinty, D., et al.: Endocrinology, 24, 829 (1939)
• Belanger, A., et al.: Steroids, 37, 361 (1939)
• Nieman, L., et al.: J. Clin. Endocrinol. Metab., 61, 536 (1939)
• Klebe, G., et al.: J. Med. Chem., 37, 4130 (1939)