(1S,2R,8R,10S,11S,14R,15S,17S)-14-(1,2-dihydroxyethyl)-8,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 170212
• Molecular Formular: C21H32O6
• Molecular Mass: 380.47518
• Monoisotopic Mass: 380.21988874
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](C[C@H]2O)[C@H]2[C@](C[C@@H]1O)([C@@](CC2)(O)C(CO)O)C)C
• Canonical SMILES: OCC([C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C[C@H](C2=CC(=O)CC[C@]12C)O)O
• InChI: InChI=1S/C21H32O6/c1-19-5-3-11(23)7-14(19)15(24)8-12-13-4-6-21(27,17(26)10-22)20(13,2)9-16(25)18(12)19/h7,12-13,15-18,22,24-27H,3-6,8-10H2,1-2H3/t12-,13-,15+,16-,17?,18+,19-,20-,21-/m0/s1
• InChIKey: BVMVQKFXKDRESB-HRKMQMLQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8R,10S,11S,14R,15S,17S)-14-(1,2-dihydroxyethyl)-8,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,8R,10S,11S,14R,15S,17S)-14-(1,2-dihydroxyethyl)-8,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (6β,11β,20RS)-6,11,17,20,21-pentahydroxypregn-4-en-3-one; 6β,11β,17,20,21-pentahydroxypregn-4-en-3-one; 6β-Hydroxy-20-dihydrocortisol; 6β-Hydroxy-20-dihydro Cortisol (Mixture of Diastereomers)

Database IDs

• PubChem SID: 164226122
• PubChem CID: 71748867

CALCULATED PROPERTIES

• Acid pKa: 12.977716
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -0.5708208
• LogD (pH = 7.4): -0.57082194
• Log P: -0.5708208
• Molar Refractivity: 99.6822 cm^3
• Polarizability: 39.47783 Å^3
• Polar Surface Area: 118.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H825345

6β-Hydroxy-20-dihydrocortisol is a metabolite of 6β-Hydroxycortisol (H922300) and 20-dihydrocortisol.

REFERENCES

• Dixon, R. et al.: Steroids, 13, 529 (1969)
• Dixon, R. et al.: Steroids, 12, 423 (1969)