(1S,2S,9R,10S,11S,14R,15S)-14-ethynyl-2,14-dihydroxy-9,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 171376
• Molecular Formular: C21H28O3
• Molecular Mass: 328.44522
• Monoisotopic Mass: 328.20384476
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)C)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C)O
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@H](C)CC2=CC(=O)CC[C@]12O
• InChI: InChI=1S/C21H28O3/c1-4-20(23)9-7-16-18-13(2)11-14-12-15(22)5-10-21(14,24)17(18)6-8-19(16,20)3/h1,12-13,16-18,23-24H,5-11H2,2-3H3/t13-,16+,17+,18+,19+,20+,21-/m1/s1
• InChIKey: YMNJMUUOXMIQOT-GWXLLEQUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,9R,10S,11S,14R,15S)-14-ethynyl-2,14-dihydroxy-9,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2S,9R,10S,11S,14R,15S)-14-ethynyl-2,14-dihydroxy-9,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (7α,17α)-17,19-Dihydroxy-7-methyl-19-norpregn-4-en-20-yn-3-one; 10β-Hydroxy Δ4-Tibolone

Database IDs

• CAS Number: 105186-35-4
• PubChem SID: 164227286
• PubChem CID: 46939249

CALCULATED PROPERTIES

• Acid pKa: 13.935046
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.422901
• LogD (pH = 7.4): 2.422901
• Log P: 2.422901
• Molar Refractivity: 93.4242 cm^3
• Polarizability: 36.46381 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 220-222°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H964270

A metabolite of Tibolone (T437505). It is an inhibitor of tyrosinase and thus useful in producing skin lightning and preserving fruits and vegetables.

REFERENCES

• Faassen, F., et al.: Pharma. Res., 20, 177 (2003)