(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyl(1,16,16,17-2H4)tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 173784
• Molecular Formular: C22H32O5
• Molecular Mass: 376.48648
• Monoisotopic Mass: 376.22497412
• SMILES: C1CC(=O)C=C2[C@]1([C@@H]1[C@@H](C[C@@H]2C)[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]2C[C@@H](C2=CC(=O)CC[C@]12C)C
• InChI: InChI=1S/C22H32O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h9,12,14-15,17,19,23,25,27H,4-8,10-11H2,1-3H3/t12-,14-,15-,17-,19?,20-,21-,22-/m0/s1
• InChIKey: FQWLSWNUHFREIQ-XRDLKPKISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyl(1,16,16,17-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyl(1,16,16,17-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (6α,11β)-11,17,21-Trihydroxy-6-methylpregn-4-ene-3,20-dione-d4; 17-Hydroxy-6α-methylcorticosterone-d4; 6α-Methyl-11β,17α,21-trihydroxy-4-pregnene-3,20-dione-d4; 6α-Methylcortisol-d4; NSC 19618-d4; U 7240-d4; 6α-Methyl Hydrocortisone-d4

Database IDs

• PubChem SID: 164229694
• PubChem CID: 71750375

CALCULATED PROPERTIES

• Acid pKa: 12.584726
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.5621855
• LogD (pH = 7.4): 1.5621827
• Log P: 1.5621855
• Molar Refractivity: 101.9486 cm^3
• Polarizability: 40.119896 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M312517

A labelled metabolite of Cortisone (C696500).

REFERENCES

• Mashkovskii, M., et al.: Med. Agents, 2, 34 (2002)