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

• ChemBase ID: 165900
• Molecular Formular: C21H32O4
• Molecular Mass: 348.47638
• Monoisotopic Mass: 348.2300595
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(C(CO)O)O)C)C
• Canonical SMILES: OCC([C@@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)O
• InChI: InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-18,22,24-25H,3-10,12H2,1-2H3/t15-,16+,17+,18?,19+,20+,21+/m1/s1
• InChIKey: XNFSGLNHLVHCFT-WMSSUOLPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-(1,2-dihydroxyethyl)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-14-(1,2-dihydroxyethyl)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: 20-Dihydro Cortexolone; 17,20,21-Trihydroxypregn-4-en-3-one; 11-Deoxy-20-dihydro Cortisol(Mixture of Diastereomers)

Database IDs

• CAS Number: 5786-59-4
• PubChem SID: 162260033
• PubChem CID: 160794

CALCULATED PROPERTIES

• Acid pKa: 12.996937
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.968755
• LogD (pH = 7.4): 1.9687539
• Log P: 1.968755
• Molar Refractivity: 96.5742 cm^3
• Polarizability: 38.18754 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dioxane
• Apperance: White Solid
• Melting Point: 178-180°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D232800

20-Dihydro derivative of the glucorticoid 11-Deoxycortisol (D232600).

REFERENCES

• Fieser, L.F. et al.: J. Biol. Chem., 156, 191 (1944)