(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

• ChemBase ID: 4257
• Molecular Formular: C27H46O2
• Molecular Mass: 402.65294
• Monoisotopic Mass: 402.34978071
• SMILES: C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CCCC(O)(C)C)C)C)C1)C
• InChI: InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
• InChIKey: INBGSXNNRGWLJU-ZHHJOTBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol; (1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-6-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: 25-hydroxycholesterol
• Synonyms: (3β)-Cholest-5-ene-3,25-diol; Cholest-5-ene-3β,25-diol; 25-Hydroxy-5-cholestene-3β-ol; 5-Cholesten-3β,25-diol; 25-Hydroxy Cholesterol; (3BETA)-CHOLEST-5-ENE-3,25-DIOL; 5-Cholestene-3β,25-diol; 25-Hydroxycholesterol; 5-胆甾烯-3β,25-二醇; 25-羟基胆甾醇

Database IDs

• CAS Number: 2140-46-7
• MDL Number: MFCD00057815
• Beilstein Number: 3161259
• PubChem SID: 46506794; 160967689
• PubChem CID: 65094

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.20429
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.641774
• LogD (pH = 7.4): 5.641774
• Log P: 5.641774
• Molar Refractivity: 122.4526 cm^3
• Polarizability: 48.564686 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.95
• LOG S: -6.22
• Solubility (Water): 2.44e-04 g/l

PROPERTIES

Physical Property

• Solubility: chloroform: soluble50 mg/mL, clear, colorless to slightly yellow

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38-48
• Safety Statements: 26-36-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335-H373
• GHS Precautionary statements: P261-P280-P305 + P351 + P338

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C27H46O2

DETAILS

DrugBank - DB04705

Drug information: experimental

Sigma Aldrich - 55125

Other Notes
Studies on the regulation mechanism for the synthesis of cholesteryl esters1

Toronto Research Chemicals - H918030

An oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It induces apoptosis in human monocytic cell lines as well as inducing apoptosis in CEM cells associated with negative reg

REFERENCES

• Aupeix, K. et al.: Immunobiology, 194, 415 (1995)
• Moog, C. et al.: Antivir. Chem, Chemother., 9, 491 (1995)
• Ayala-Torres, S. et al.: Exp. Cell Res., 246, 193 (1995)