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

• ChemBase ID: 132284
• 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-GFKLAVDKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15S)-14-[(2S,3R)-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: 22R-hydroxycholesterol
• Synonyms: 22α-Hydroxycholesterol; 5-Cholestene-3β,22(R)-diol; 5-Cholestene-3β,22[R]-diol; 22(R)-Hydroxycholesterol; 22α-Hydroxy Cholesterol; (3β,22R)-Cholest-5-ene-3,22-diol; (20S,22R)-Cholest-5-ene-3β,22-diol; (22R)-22-Hydroxycholesterol; (22R)-Cholest-5-ene-3β,22-diol; (22R)-Hydroxycholesterol; Cholest-5-ene-3β,22(R)-diol; Narthesterol

Database IDs

• CAS Number: 17954-98-2
• MDL Number: MFCD00070042
• PubChem SID: 24895852; 162226561
• PubChem CID: 167685

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

• Purity: ≥98%

DETAILS

Sigma Aldrich - H9384

Frequently Asked Questions
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Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H9384.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - H918015

The 22R-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)