4b-Hydroxycholesterol (CHEM041401)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:26:48 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041401
Identification
Common Name4b-Hydroxycholesterol
ClassSmall Molecule
Description4b-Hydroxycholesterol is a new endogenous CYP3A marker: relationship to CYP3A5 genotype, quinine 3-hydroxylation and sex in Koreans, Swedes and Tanzanians
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta,4beta)-Cholest-5-ene-3,4-diolChEBI
Cholest-5-en-3beta,4beta-diolChEBI
(3b,4b)-Cholest-5-ene-3,4-diolGenerator
(3Β,4β)-cholest-5-ene-3,4-diolGenerator
Cholest-5-en-3b,4b-diolGenerator
Cholest-5-en-3β,4β-diolGenerator
(4b)-Cholest-5-ene-3b,4-diolHMDB
(4b)-4-HydroxycholesterolHMDB
(4b)-Cholest-5-ene-3beta,4-diolHMDB
4-HydroxycholesterolHMDB
4b-Cholest-5-ene-3b,4-diolHMDB
4beta-HydroxycholesterolHMDB
Cholest-5-en-3beta,4b-diolHMDB
Cholest-5-ene-3,4-diolHMDB
Cholest-5-ene-3b,4b-diolHMDB
(3beta,4alpha)-Isomer OF cholest-5-ene-3,4-diolHMDB
Cholest-5-ene-3beta,4beta-diolHMDB
4b-Hydroxy-cholesterolGenerator
4Β-hydroxy-cholesterolGenerator
Chemical FormulaC27H46O2
Average Molecular Mass402.653 g/mol
Monoisotopic Mass402.350 g/mol
CAS Registry NumberNot Available
IUPAC Name(1S,2R,5S,6R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,6-diol
Traditional Name4β-hydroxy-cholesterol
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI IdentifierInChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25-,26-,27-/m1/s1
InChI KeyCZDKQKOAHAICSF-JSAMMMMSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00027 g/LALOGPS
logP6.16ALOGPS
logP6.19ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)13.5ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.82 m³·mol⁻¹ChemAxon
Polarizability51.39 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00du-0009000000-0351b773b1211703e75cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-4000490000-159f0e29d7e026e00111Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0115900000-3ebcc7139ebce8b89074Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmr-3119100000-b8561eae42d8f8feffaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9278000000-f0fd6fb0889e6e628ae6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-0ead5eafbeb66d5b905bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0003900000-d36392856ffd1de06a41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n3-1009000000-e6e663cf5dfe2241046fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1005900000-83a1b4f4135fe0167748Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fr6-7039200000-69176898a1c750445f8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9830000000-ca9ae0e8c0692ff1ea68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-079f76b4d985e4b92c9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-164f416843343e4c65e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0009000000-6cfbf1b372f43a5b222dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013643
FooDB IDFDB029614
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID2497521
ChEBI ID85778
PubChem Compound ID3247060
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97.
6. O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26.
7. Bodin K, Bretillon L, Aden Y, Bertilsson L, Broome U, Einarsson C, Diczfalusy U: Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4. J Biol Chem. 2001 Oct 19;276(42):38685-9. Epub 2001 Aug 20.
8. Bodin K, Andersson U, Rystedt E, Ellis E, Norlin M, Pikuleva I, Eggertsen G, Bjorkhem I, Diczfalusy U: Metabolism of 4 beta -hydroxycholesterol in humans. J Biol Chem. 2002 Aug 30;277(35):31534-40. Epub 2002 Jun 20.
9. Wide K, Larsson H, Bertilsson L, Diczfalusy U: Time course of the increase in 4beta-hydroxycholesterol concentration during carbamazepine treatment of paediatric patients with epilepsy. Br J Clin Pharmacol. 2008 May;65(5):708-15. doi: 10.1111/j.1365-2125.2007.03078.x. Epub 2008 Feb 12.
10. Diczfalusy U, Miura J, Roh HK, Mirghani RA, Sayi J, Larsson H, Bodin KG, Allqvist A, Jande M, Kim JW, Aklillu E, Gustafsson LL, Bertilsson L: 4Beta-hydroxycholesterol is a new endogenous CYP3A marker: relationship to CYP3A5 genotype, quinine 3-hydroxylation and sex in Koreans, Swedes and Tanzanians. Pharmacogenet Genomics. 2008 Mar;18(3):201-8. doi: 10.1097/FPC.0b013e3282f50ee9.
11. Diczfalusy U, Kanebratt KP, Bredberg E, Andersson TB, Bottiger Y, Bertilsson L: 4beta-hydroxycholesterol as an endogenous marker for CYP3A4/5 activity. Stability and half-life of elimination after induction with rifampicin. Br J Clin Pharmacol. 2009 Jan;67(1):38-43. doi: 10.1111/j.1365-2125.2008.03309.x. Epub 2008 Nov 6.
12. Goodenough AK, Onorato JM, Ouyang Z, Chang S, Rodrigues AD, Kasichayanula S, Huang SP, Turley W, Burrell R, Bifano M, Jemal M, LaCreta F, Tymiak A, Wang-Iverson D: Quantification of 4-beta-hydroxycholesterol in human plasma using automated sample preparation and LC-ESI-MS/MS analysis. Chem Res Toxicol. 2011 Sep 19;24(9):1575-85. doi: 10.1021/tx2001898. Epub 2011 Jul 21.
13. Breuer O: Identification and quantitation of cholest-5-ene-3 beta,4 beta-diol in rat liver and human plasma. J Lipid Res. 1995 Nov;36(11):2275-81.
14. The lipid handbook with CD-ROM
15. Triglycerides and Cholesterol Research
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20. https://www.ncbi.nlm.nih.gov/pubmed/?term=19006545
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23. https://www.ncbi.nlm.nih.gov/pubmed/?term=8656065