(1S,2S,7S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-one

• ChemBase ID: 167560
• Molecular Formular: C21H32O5
• Molecular Mass: 364.47578
• Monoisotopic Mass: 364.22497412
• SMILES: C1CC(=O)C[C@H]2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)CO)O)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CC[C@@H]2[C@]1(C)CCC(=O)C2
• InChI: InChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12,14-16,18,22,24,26H,3-11H2,1-2H3/t12-,14-,15-,16-,18+,19-,20-,21-/m0/s1
• InChIKey: ACSFOIGNUQUIGE-SERXDUEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,7S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• IUPAC Traditional name: (1S,2S,7S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• Synonyms: 11β,17,21-Trihydroxy-5α-pregnane-3,20-dione; 11β,17α,21-Trihydroxy-5α-pregnane-3,20-dione; 5α-Dihydrocortisol; 5α-Pregnan-11β,17α,21-triol-3,20-dione; Allodihydrocortisol; Allodihydrohydrocortisone; Allopregnane-11β,17α,21-triol-3,20-dione; Hydrallostane; 5α-Dihydrocortisol

Database IDs

• CAS Number: 516-41-6
• PubChem SID: 162261693
• PubChem CID: 12816693

CALCULATED PROPERTIES

• Acid pKa: 12.584778
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.3210007
• LogD (pH = 7.4): 1.320998
• Log P: 1.3210008
• Molar Refractivity: 96.5733 cm^3
• Polarizability: 38.530174 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 210-212°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D448860

Metabolite of Cortisol.

REFERENCES

• Clark, D. et al.: Steroids 7, 352 (2006)