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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 09:27:14 UTC
Update Date2017-12-20 20:32:55 UTC
HMDB IDHMDB0004035
Secondary Accession Numbers
  • HMDB04035
Metabolite Identification
Common Name22b-Hydroxycholesterol
Description22R-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, 22R-hydroxycholesterol is considered to be a sterol lipid molecule. 22R-Hydroxycholesterol is considered to be a practically insoluble (in water) and relatively neutral molecule. 22R-Hydroxycholesterol has been found in human epidermis, hepatic tissue and endocrine gland tissues, and has also been primarily detected in urine. Within the cell, 22R-hydroxycholesterol is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, 22R-hydroxycholesterol is involved in the steroidogenesis pathway. 22R-Hydroxycholesterol is also involved in several metabolic disorders, some of which include adrenal hyperplasia type 3 or congenital adrenal hyperplasia due to 21-hydroxylase deficiency, the apparent mineralocorticoid excess syndrome pathway, 11-beta-hydroxylase deficiency (cyp11b1), and the congenital lipoid adrenal hyperplasia (clah) or lipoid cah pathway.
Structure
Thumb
Synonyms
ValueSource
(3beta,22R)-Cholest-5-ene-3,22-diolChEBI
22beta-HydroxycholesterolChEBI
22R-HydroxycholesterolChEBI
Cholest-5-en-3beta,22R-diolChEBI
(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)-isomerMeSH
22-Hydroxycholesterol, (3beta,20R,22S)-isomerMeSH
(22R)-22-HydroxycholesterolMeSH
Cholest-5-ene-3beta,22-diolMeSH
22(R)-HydroxycholesterolMeSH
22-Hydroxycholesterol, (3beta,22S)-isomerMeSH
22(R)OH CholesterolMeSH
22-HydroxycholesterolMeSH
22-Hydroxycholesterol, (3beta,22R)-isomerMeSH
22S-HydroxycholesterolMeSH
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
DescriptionThis compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These 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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00065 g/LALOGPS
logP5.69ALOGPS
logP5.8ChemAxon
logS-5.8ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-1009000000-ed60780a407ecfba86a3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-2111490000-e04dc3bb7ab36f5571f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0009200000-2ae8fb6172d46e818cefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2119100000-9925177c38f63ddc14a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6049000000-44d8c7fcd6055391f8ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0004900000-10b9f0186b2a2ac37d53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-1019700000-6b5a6ee8410d635f82c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-4059000000-8d88574ef4b0b7d39b85View in MoNA
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
FoodDB IDFDB023285
KNApSAcK IDNot Available
Chemspider ID146693
KEGG Compound IDC05502
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7006
PubChem Compound167685
PDB IDHC9
ChEBI ID67237
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