(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[2-hydroxy(2H2)acetyl]-2,15-dimethyl(4,4,6,8,8-2H5)tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 165877
• Molecular Formular: C21H30O4
• Molecular Mass: 346.4605
• Monoisotopic Mass: 346.21440944
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(C(=O)CO)O)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C21H30O4/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/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1
• InChIKey: WHBHBVVOGNECLV-OBQKJFGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,15-dimethyl(4,4,6,8,8-^2H₅)tetracyclo[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-hydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,15-dimethyl(4,4,6,8,8-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: 11-Deoxy-17-hydroxycorticosterone-d7; 17,21-Dihydroxypregn-4-en-3,20-dione-d7; 4-Pregnene-17α,21-diol-3,20-dione-d7; Cortexolone-d7; Cortifen-d7; NSC 18317-d7; Reichstein S-d7; Reichstein's Compound S-d7; SKF 3050-d7; 11-Deoxy Cortisol-d7 (Major)

Database IDs

• PubChem SID: 162260010
• PubChem CID: 59476907

CALCULATED PROPERTIES

• Acid pKa: 12.591038
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.5839312
• LogD (pH = 7.4): 2.5839283
• Log P: 2.5839312
• Molar Refractivity: 95.8075 cm^3
• Polarizability: 37.642807 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dioxane; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 187-194°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D232602

Glucocorticoid receptor binding.A representative lots showed approximately 10% d8.

REFERENCES

• Gazdar, A., et al.: Cancer Res., 50, 5488, (1990)
• Bird, I., et al.: Endocrinology, 134, 2468 (1990)
• Auchus, R., et al.: J. Biol. Chem., 273, 3158 (1990)
• Dardis, A., et al.: J. Endocrinol., 179, 131 (1990)