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

• ChemBase ID: 175660
• 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)(CC)[C@](CC2)(O)C#C
• 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-SYAJIYQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10S,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,10S,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: (8α,17α)-(±)-13-Ethyl-17-hydroxy-18,19-dinorpregn-5(10)-en-20-yn-3-one; (±)-13-Ethyl-17-hydroxy-18,19-dinor-8α,17α-pregn-5(10)-en-20-yn-3-one; 8α-5,10-Dehydro-Norgestrel; rac 8α-[Δ-5(10)]-Norgestrel

Database IDs

• CAS Number: 5541-87-7
• PubChem SID: 164231570
• PubChem CID: 71751217

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

DETAILS

Toronto Research Chemicals - N689550

An impurity of the ovulation inhibiting steroid Norgestrel (N689500).

REFERENCES

• Fotherby, K., et al.: J. Steroid Biochem., 19(1C), 817 (1983)
• Stanczyk, F. Z., et al.: Contraception, 42, 67 (1983)