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

• ChemBase ID: 155108
• Molecular Formular: C27H46O2
• Molecular Mass: 402.65294
• Monoisotopic Mass: 402.34978071
• SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2CC=C2[C@@]1(CC[C@@H](C2)O)C)C)[C@H](CCC(C)C)O
• Canonical SMILES: CC(CC[C@@H]([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-QUOSNDFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15S)-14-[(2S,3S)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC Traditional name: 22β-hydroxycholesterol
• Synonyms: 22β-Hydroxycholesterol; 5-Cholestene-3β,22(S)-diol; 22(S)-Hydroxycholesterol; (3β,22S)-Cholest-5-ene-3,22-diol; (20S,22S)-Cholest-5-ene-3β,22-diol; (22S)-22-Hydroxycholesterol; (22S)-Cholest-5-ene-3β,22-diol; (22β)-Hydroxycholesterol; Cholest-5-ene-3β,22(S)-diol; Narthesterol; 22β-Hydroxy Cholesterol

Database IDs

• CAS Number: 22348-64-7
• MDL Number: MFCD00010476
• PubChem SID: 162249246; 24895715
• PubChem CID: 168038

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

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C27H46O2

DETAILS

Toronto Research Chemicals - H918020

The 22S-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)