(10S,11S,14S,15S,17R)-17-[4-(dimethylamino)phenyl]-14-hydroxy-14-(3-hydroxyprop-1-yn-1-yl)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-1,6-dien-5-one

• ChemBase ID: 170931
• Molecular Formular: C29H35NO3
• Molecular Mass: 445.5931
• Monoisotopic Mass: 445.26169399
• SMILES: C1CC(=O)C=C2C1=C1[C@@H](CC2)[C@H]2[C@](C[C@@H]1c1ccc(cc1)N(C)C)([C@](CC2)(O)C#CCO)C
• Canonical SMILES: OCC#C[C@]1(O)CC[C@@H]2[C@]1(C)C[C@H](c1ccc(cc1)N(C)C)C1=C3CCC(=O)C=C3CC[C@@H]21
• InChI: InChI=1S/C29H35NO3/c1-28-18-25(19-5-8-21(9-6-19)30(2)3)27-23-12-10-22(32)17-20(23)7-11-24(27)26(28)13-15-29(28,33)14-4-16-31/h5-6,8-9,17,24-26,31,33H,7,10-13,15-16,18H2,1-3H3/t24-,25+,26-,28-,29-/m0/s1
• InChIKey: ULLTWLWXPJPTQG-GCNJZUOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S,11S,14S,15S,17R)-17-[4-(dimethylamino)phenyl]-14-hydroxy-14-(3-hydroxyprop-1-yn-1-yl)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-dien-5-one
• IUPAC Traditional name: (10S,11S,14S,15S,17R)-17-[4-(dimethylamino)phenyl]-14-hydroxy-14-(3-hydroxyprop-1-yn-1-yl)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-dien-5-one
• Synonyms: (11β,17β)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-17-(3-hydroxy-1-propyn-1-yl)-estra-4,9-dien-3-one; RU 42698; 22-Hydroxy Mifepristone

Database IDs

• CAS Number: 105012-15-5
• PubChem SID: 164226841
• PubChem CID: 13605512

CALCULATED PROPERTIES

• Acid pKa: 12.792017
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.7573466
• LogD (pH = 7.4): 3.851177
• Log P: 3.8525164
• Molar Refractivity: 134.3556 cm^3
• Polarizability: 50.64332 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Yellow Solid
• Melting Point: 102-106°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H948445

A metabolite of Mifepristone.

REFERENCES

• Heikinheimo, O., et al.: J. Steroid Biochem., 26, 279 (1987)
• Brogden, R., et al.: Drugs, 45, 384 (1987)
• Shi, Y., et al.: Contraception, 48, 133 (1987)
• Jang, G., et al.: Biochem. Pharmacol., 52, 753 (1987)
• Gainer, E., et al.: Steroids, 68, 1005 (1987)