(1S,2R,5S,10S,11S,14R,15S)-14-[(2S)-3-hydroxy-6-(2H3)methyl(4,4,5,5,6,7,7,7-2H8)heptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-ol

• ChemBase ID: 170351
• Molecular Formular: C27H46O2
• Molecular Mass: 402.65294
• Monoisotopic Mass: 402.34978071
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](C(CCC(C)C)O)C)C)O
• Canonical SMILES: CC(CCC([C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C)O)C
• InChI: InChI=1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25?,26-,27+/m0/s1
• InChIKey: RZPAXNJLEKLXNO-UKNNTIGFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15S)-14-[(2S)-3-hydroxy-6-(^2H₃)methyl(4,4,5,5,6,7,7,7-^2H₈)heptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC Traditional name: (1S,2R,5S,10S,11S,14R,15S)-14-[(2S)-3-hydroxy-6-(^2H₃)methyl(4,4,5,5,6,7,7,7-^2H₈)heptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• Synonyms: (3β)-Cholest-5-ene-3,22-diol-d11; Cholest-5-ene-3β,22-diol-d11; 22-Hydroxy Cholesterol-d11(Mixture of Diastereomers)

Database IDs

• PubChem SID: 164226261
• PubChem CID: 71748936

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.804124
• LogD (pH = 7.4): 5.8041244
• Log P: 5.8041244
• Molar Refractivity: 122.209 cm^3
• Polarizability: 48.564686 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H918012

A labelled metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.

REFERENCES

• Samson, M., et al.: J. Biol. Chem., 272, 24934 (1997)
• Mackay, C., et al.: Nature Immunol., 2, 95 (1997)
• Navenot, J., et al.: J. Mol. Biol., 313, 1181 (1997)