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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2011-01-28 11:52:27 UTC
Update Date2022-03-07 02:51:34 UTC
HMDB IDHMDB0013643
Secondary Accession Numbers
  • HMDB13643
Metabolite Identification
Common Name4b-Hydroxycholesterol
Description4b-Hydroxycholesterol, also known as cholest-5-en-3b,4b-diol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4b-hydroxycholesterol is considered to be a sterol lipid molecule. 4b-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582753139
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 Weight402.6529
Monoisotopic Molecular Weight402.349780716
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
CAS Registry NumberNot Available
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 Identifier
InChI=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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.07731661259
DarkChem[M-H]-197.69731661259
DeepCCS[M-2H]-244.42230932474
DeepCCS[M+Na]+218.59530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4b-Hydroxycholesterol[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)C2653.3Standard polar33892256
4b-Hydroxycholesterol[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)C3310.2Standard non polar33892256
4b-Hydroxycholesterol[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)C3329.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4b-Hydroxycholesterol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3228.0Semi standard non polar33892256
4b-Hydroxycholesterol,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3258.5Semi standard non polar33892256
4b-Hydroxycholesterol,2TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3194.9Semi standard non polar33892256
4b-Hydroxycholesterol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3471.3Semi standard non polar33892256
4b-Hydroxycholesterol,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3500.3Semi standard non polar33892256
4b-Hydroxycholesterol,2TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3662.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4b-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00du-0009000000-0351b773b1211703e75c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4b-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positivesplash10-001i-4000490000-159f0e29d7e026e001112017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4b-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 10V, Positive-QTOFsplash10-0udi-0115900000-3ebcc7139ebce8b890742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 20V, Positive-QTOFsplash10-0kmr-3119100000-b8561eae42d8f8feffae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 40V, Positive-QTOFsplash10-0ab9-9278000000-f0fd6fb0889e6e628ae62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0001900000-0ead5eafbeb66d5b905b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 20V, Negative-QTOFsplash10-0udi-0003900000-d36392856ffd1de06a412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 40V, Negative-QTOFsplash10-05n3-1009000000-e6e663cf5dfe2241046f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 10V, Positive-QTOFsplash10-0udi-1005900000-83a1b4f4135fe01677482021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 20V, Positive-QTOFsplash10-0fr6-7039200000-69176898a1c750445f8d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 40V, Positive-QTOFsplash10-0ab9-9830000000-ca9ae0e8c0692ff1ea682021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 20V, Negative-QTOFsplash10-0udi-0000900000-164f416843343e4c65e82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 40V, Negative-QTOFsplash10-0002-0009000000-6cfbf1b372f43a5b222d2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.055 +/- 0.002 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.014 +/- 0.0005 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029614
KNApSAcK IDNot Available
Chemspider ID2497521
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3247060
PDB IDNot Available
ChEBI ID85778
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  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. [PubMed:15254070 ]
  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. [PubMed:23625372 ]
  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. [PubMed:11514559 ]
  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. [PubMed:12077124 ]
  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. [PubMed:18279471 ]
  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. [PubMed:18300941 ]
  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. [PubMed:19006545 ]
  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. [PubMed:21728364 ]
  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. [PubMed:8656065 ]
  14. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  15. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..