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Record Information
Version3.6
Creation Date2006-08-16 14:44:11 UTC
Update Date2013-05-29 19:31:32 UTC
HMDB IDHMDB01419
Secondary Accession NumbersNone
Metabolite Identification
Common Name24-Hydroxycholesterol
Description24-Hydroxycholesterol (24OHC) is almost exclusively formed in the brain. The enzymatic conversion of CNS cholesterol to 24OHC, which readily crosses the blood-brain barrier, is the major pathway for brain cholesterol elimination and brain cholesterol homeostasis maintenance. The enzyme mediating this conversion has been characterized at the molecular level as cholesterol 24-hydroxylase (EC 1.14.13.98, CYP46) and is mainly located in neurons. Like other oxysterols, 24OHC is efficiently converted into normal bile acids or excreted in bile in its sulfated and glucuronidated form. Levels of 24OHC in the circulation decrease with age in infants and children. In adults, however, the levels appear to be stable. There is accumulating evidence pointing toward a potentially important link between cholesterol, beta-amyloid, and Alzheimer's disease. Patients with active demyelinating diseases had increased levels of 24OHC in cerebrospinal fluid (CSF). Patients with Alzheimer's disease have slightly increased levels of 24OHC in CSF. Patients with multiple sclerosis have a tendency to have higher levels of 24OHC during active periods. (PMID: 15061359 , 14574622 ).
Structure
Thumb
Synonyms
  1. (24S)-24-Hydroxycholesterol
  2. (24S)-cholest-5-ene-3b,24-diol
  3. (24S)-cholest-5-ene-3beta,24-diol
  4. 24(S)-Hydroxycholesterol
  5. 24-Hydroxycholesterol
  6. 24S-Cholest-5-ene-3b,24-diol
  7. 24S-Hydroxycholesterol
  8. Cerebrosterin
  9. Cerebrosterol
  10. Cholest-5-en-3b,24S-diol
  11. Cholest-5-en-3beta,24S-diol
  12. Cholest-5-ene-3,24-diol
  13. Cholest-5-ene-3b,24b-diol
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional Name24-hydroxycholesterol
CAS Registry Number474-73-7
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)C
InChI Identifier
InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(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-/m1/s1
InChI KeyIOWMKBFJCNLRTC-XWXSNNQWSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassCholesterols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
Substituents
  • 24 Hydroxy Steroid
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Bile Acid, Alcohol, Or Derivative
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Dihydroxy Bile Acid, Alcohol, Or Derivative
  • Hydroxy Bile Acid, Alcohol, Or Derivative
  • Secondary Alcohol
  • Sesterterpene
Direct ParentCholesterols and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
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 Solubility0.000403ALOGPS
logP5.7ALOGPS
logP5.8ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.21 m3·mol-1ChemAxon
Polarizability51.14 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035map00120
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.049 +/- 0.002 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.006 +/- 0.0003 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0018 +/- 0.00052 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0034 (0.0033-0.0036) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11 +/- 0.03 uMAdult (>18 years old)Not Specified
Hypercholesterolemia
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0061 (0.0058-0.0064) uMElderly (>65 years old)BothAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.016 (0.014-0.017) uMAdult (>18 years old)BothAcute or chronic demyelinating polyneuropathies details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0045 (0.0041-0.0050) uMAdult (>18 years old)BothSubarachnoid hemorrhage details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0086 (0.0076-0.0096) uMAdult (>18 years old)Both
Meningitis
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0062 (0.0057-0.0068) uMAdult (>18 years old)BothNeuroborreliosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0077 (0.0066-0.0093) uMAdult (>18 years old)Not Specified
Mild cognitive impairment
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.004 +/- 0.0013 uMAdult (>18 years old)BothMultiple Sclerosis details
Associated Disorders and Diseases
Disease References
Demyelinating polyneuropathy
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. Pubmed: 15061359
Alzheimer's disease
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. Pubmed: 15061359
Subarachnoid hemorrhage
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. Pubmed: 15061359
Hypercholesterolemia
  1. Thelen KM, Laaksonen R, Paiva H, Lehtimaki T, Lutjohann D: High-dose statin treatment does not alter plasma marker for brain cholesterol metabolism in patients with moderately elevated plasma cholesterol levels. J Clin Pharmacol. 2006 Jul;46(7):812-6. Pubmed: 16809807
Meningitis
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. Pubmed: 15061359
Mild cognitive impairment
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. Pubmed: 15061359
Multiple sclerosis
  1. Leoni V, Lutjohann D, Masterman T: Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J Lipid Res. 2005 Feb;46(2):191-5. Epub 2004 Dec 1. Pubmed: 15576852
Neuroborreliosis
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. Pubmed: 15061359
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022611
KNApSAcK IDNot Available
Chemspider ID108790
KEGG Compound IDC13550
BioCyc IDCPD-7239
BiGG ID2197434
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01419
Metagene LinkHMDB01419
METLIN IDNot Available
PubChem Compound121948
PDB IDNot Available
ChEBI ID34310
References
Synthesis ReferencePrasad V V; Ponticorvo L; Lieberman S Identification of 24-hydroxycholesterol in bovine adrenals in both free and esterified forms and in bovine brains as its sulfate ester. Journal of steroid biochemistry (1984), 21(6), 733-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. Pubmed: 15061359
  2. Lutjohann D, von Bergmann K: 24S-hydroxycholesterol: a marker of brain cholesterol metabolism. Pharmacopsychiatry. 2003 Sep;36 Suppl 2:S102-6. Pubmed: 14574622

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Involved in the turnover of cholesterol. It converts cholesterol into 24S-hydroxycholesterol and, to a lesser extent, 25-hydroxycholesterol.
Gene Name:
CYP46A1
Uniprot ID:
Q9Y6A2
Molecular weight:
56820.535
Reactions
Cholesterol + NADPH + Oxygen → 24-Hydroxycholesterol + NADP + Waterdetails