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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 09:27:14 UTC
Update Date2021-09-14 15:40:09 UTC
HMDB IDHMDB0004035
Secondary Accession Numbers
  • HMDB04035
Metabolite Identification
Common Name22b-Hydroxycholesterol
Description22b-Hydroxycholesterol, also known as cholest-5-en-3b,22R-diol or 22(R)OH cholesterol, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Thus, 22b-hydroxycholesterol is considered to be a sterol lipid molecule. 22b-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752295
Synonyms
ValueSource
(3beta,22R)-Cholest-5-ene-3,22-diolChEBI
22beta-HydroxycholesterolChEBI
22R-HydroxycholesterolChEBI
Cholest-5-en-3beta,22R-diolChEBI
(22R)-22-HydroxycholesterolKegg
(3b,22R)-Cholest-5-ene-3,22-diolGenerator
(3Β,22R)-cholest-5-ene-3,22-diolGenerator
22Β-hydroxycholesterolGenerator
Cholest-5-en-3b,22R-diolGenerator
Cholest-5-en-3β,22R-diolGenerator
22-Hydroxycholesterol, (3beta,20R,22R)-isomerHMDB
22-Hydroxycholesterol, (3beta,20R,22S)-isomerHMDB
Cholest-5-ene-3beta,22-diolHMDB
22(R)-HydroxycholesterolHMDB
22-Hydroxycholesterol, (3beta,22S)-isomerHMDB
22(R)OH CholesterolHMDB
22-HydroxycholesterolHMDB
22-Hydroxycholesterol, (3beta,22R)-isomerHMDB
22S-HydroxycholesterolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(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
Traditional Name22R-hydroxycholesterol
CAS Registry Number22348-64-7
SMILES
[H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
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
InChI KeyRZPAXNJLEKLXNO-GFKLAVDKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • Dihydroxy bile acid, alcohol, or derivatives
  • 22-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • 3-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M-H]-Not Available217.739http://allccs.zhulab.cn/database/detail?ID=AllCCS00000273
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00065 g/LALOGPS
logP10(5.69) g/LALOGPS
logP10(5.8) g/LChemAxon
logS10(-5.8) g/LALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.21 m³·mol⁻¹ChemAxon
Polarizability50.77 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+196.06131661259
DarkChem[M-H]-199.22831661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
22b-Hydroxycholesterol,1TMS,#1CC(C)CC[C@@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3351.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
22b-Hydroxycholesterol,1TMS,#2CC(C)CC[C@@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3351.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
22b-Hydroxycholesterol,2TMS,#1CC(C)CC[C@@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3354.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
22b-Hydroxycholesterol,1TBDMS,#1CC(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3603.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
22b-Hydroxycholesterol,1TBDMS,#2CC(C)CC[C@@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3574.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
22b-Hydroxycholesterol,2TBDMS,#1CC(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3850.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 22b-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-1009000000-ed60780a407ecfba86a32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 22b-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positivesplash10-001i-2111490000-e04dc3bb7ab36f5571f82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 22b-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 22b-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 - 22b-Hydroxycholesterol 10V, Positive-QTOFsplash10-0f79-0009200000-2ae8fb6172d46e818cef2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 20V, Positive-QTOFsplash10-00kr-2119100000-9925177c38f63ddc14a12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 40V, Positive-QTOFsplash10-0a4i-6049000000-44d8c7fcd6055391f8dd2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0004900000-10b9f0186b2a2ac37d532016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 20V, Negative-QTOFsplash10-0ue9-1019700000-6b5a6ee8410d635f82c62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 40V, Negative-QTOFsplash10-0f79-4059000000-8d88574ef4b0b7d39b852016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 10V, Positive-QTOFsplash10-0gbi-0109200000-bd7670f27e11ece2eac02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 20V, Positive-QTOFsplash10-014r-5339000000-858a48abc2f1b02935f52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 40V, Positive-QTOFsplash10-0a4l-6960000000-73b0982e9fcef4fa83d02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0000900000-84d3363c4aa86f104c552021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 20V, Negative-QTOFsplash10-0udi-0012900000-973e1345841477d95a762021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 22b-Hydroxycholesterol 40V, Negative-QTOFsplash10-0uea-7049300000-8042d2ca5cd8469196da2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue Locations
  • Adrenal Cortex
  • Epidermis
  • Fibroblasts
  • Neuron
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023285
KNApSAcK IDNot Available
Chemspider ID146693
KEGG Compound IDC05502
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7006
PubChem Compound167685
PDB IDNot Available
ChEBI ID67237
Food Biomarker OntologyNot Available
VMH IDM00606
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKoreeda, Masato; Ricca, Daniel J. Chirality transfer in stereoselective synthesis. A highly stereocontrolled synthesis of 22-hydroxylated steroid side chains via the [2,3]-Wittig rearrangement. Journal of Organic Chemistry (1986), 51(21), 4090-2.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Haidar B, Denis M, Marcil M, Krimbou L, Genest J Jr: Apolipoprotein A-I activates cellular cAMP signaling through the ABCA1 transporter. J Biol Chem. 2004 Mar 12;279(11):9963-9. Epub 2003 Dec 29. [PubMed:14701824 ]
  2. Yao ZX, Brown RC, Teper G, Greeson J, Papadopoulos V: 22R-Hydroxycholesterol protects neuronal cells from beta-amyloid-induced cytotoxicity by binding to beta-amyloid peptide. J Neurochem. 2002 Dec;83(5):1110-9. [PubMed:12437582 ]
  3. Matsuzaki J, Tsuji T, Imazeki I, Ikeda H, Nishimura T: Immunosteroid as a regulator for Th1/Th2 balance: its possible role in autoimmune diseases. Autoimmunity. 2005 Aug;38(5):369-75. [PubMed:16227152 ]
  4. Tuckey RC: Cholesterol side-chain cleavage by mitochondria from the human placenta. Studies using hydroxycholesterols as substrates. J Steroid Biochem Mol Biol. 1992 Sep;42(8):883-90. [PubMed:1525048 ]
  5. Hanley K, Ng DC, He SS, Lau P, Min K, Elias PM, Bikle DD, Mangelsdorf DJ, Williams ML, Feingold KR: Oxysterols induce differentiation in human keratinocytes and increase Ap-1-dependent involucrin transcription. J Invest Dermatol. 2000 Mar;114(3):545-53. [PubMed:10692116 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular weight:
60101.87
Reactions
Cholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion → 22b-Hydroxycholesterol + Water + Oxidized adrenal ferredoxindetails
22b-Hydroxycholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion → 20a,22b-Dihydroxycholesterol + Water + Oxidized adrenal ferredoxindetails