(1S,2R,8R,10R,11S,14R,15R)-15-ethyl-14-ethynyl-8,14-dihydroxytetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 170234
• Molecular Formular: C21H28O3
• Molecular Mass: 328.44522
• Monoisotopic Mass: 328.20384476
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](C[C@H]2O)[C@H]2[C@@](CC1)([C@@](CC2)(C#C)O)CC
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@@]1(CC)CC[C@H]1[C@H]2C[C@H](C2=CC(=O)CC[C@H]12)O
• InChI: InChI=1S/C21H28O3/c1-3-20-9-7-15-14-6-5-13(22)11-17(14)19(23)12-16(15)18(20)8-10-21(20,24)4-2/h2,11,14-16,18-19,23-24H,3,5-10,12H2,1H3/t14-,15-,16-,18+,19-,20-,21+/m1/s1
• InChIKey: LUDPEOWAWHAHEP-UGLQFRMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8R,10R,11S,14R,15R)-15-ethyl-14-ethynyl-8,14-dihydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,8R,10R,11S,14R,15R)-15-ethyl-14-ethynyl-8,14-dihydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (6β,17α)-13-Ethyl-6,17-dihydroxy-18,19-dinorpregn-4-en-20-yn-3-one; 6β-Hydroxy Norgestrel

Database IDs

• CAS Number: 55555-97-0
• PubChem SID: 164226144
• PubChem CID: 71748887

CALCULATED PROPERTIES

• Acid pKa: 14.553155
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.4309855
• LogD (pH = 7.4): 2.4309855
• Log P: 2.4309855
• Molar Refractivity: 93.541 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 - H825700

A hydroxylated impurity of Norgestrel (N689500).

REFERENCES

• Lin, Y., et al.: Biochim. Biophys. Acta, 218, 526 (1970)
• Smith, K., et al.: J. Steroid Biochem., 32, 445 (1970)
• Hu, S., et al.: Steroids, 60, 337 (1970)