Human Metabolome Database Version 3.5

Showing metabocard for 24-Hydroxycholesterol (HMDB01419)

Record Information
Version 3.5
Creation Date 2006-08-16 08:44:11 -0600
Update Date 2013-05-29 13:31:32 -0600
HMDB ID HMDB01419
Secondary Accession Numbers None
Metabolite Identification
Common Name 24-Hydroxycholesterol
Description 24-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 Link_out, 14574622 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C27H46O2
Average Molecular Weight 402.6529
Monoisotopic Molecular Weight 402.349780716
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 IUPAC Name 24-hydroxycholesterol
CAS Registry Number 474-73-7
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 Key IOWMKBFJCNLRTC-XWXSNNQWSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Cholesterols 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 Parent Cholesterols and Derivatives
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.030E-04 g/L ALOGPS
LogP 5.70 ALOGPS
LogP 5.8 ChemAxon
LogS -6.00 ALOGPS
pKa (strongest acidic) 18.2 ChemAxon
pKa (strongest basic) -0.95 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 40.46 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 122.21 ChemAxon
Polarizability 51.14 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 map00120 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.049 +/- 0.002 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.006 +/- 0.0003 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.0018 +/- 0.00052 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0034 (0.0033-0.0036) uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.11 +/- 0.03 uM Adult (>18 years old) Not Specified Comment Hypercholesterolemia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0061 (0.0058-0.0064) uM Elderly (>65 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.016 (0.014-0.017) uM Adult (>18 years old) Both Acute or chronic demyelinating polyneuropathies
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0045 (0.0041-0.0050) uM Adult (>18 years old) Both Subarachnoid haemorrhage
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0086 (0.0076-0.0096) uM Adult (>18 years old) Both Comment Meningitis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0062 (0.0057-0.0068) uM Adult (>18 years old) Both Neuroborreliosis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0077 (0.0066-0.0093) uM Adult (>18 years old) Not Specified Comment Mild cognitive impairment
Cerebrospinal Fluid (CSF) Detected and Quantified 0.004 +/- 0.0013 uM Adult (>18 years old) Both Multiple Sclerosis
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  • 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 Link_out
      Demyelinating polyneuropathy
      • 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 Link_out
          Subarachnoid hemorrhage
          • 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 Link_out
              Meningitis
              • 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 Link_out
                  Neuroborreliosis
                  • 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 Link_out
                      Mild cognitive impairment
                      • 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 Link_out
                          Hypercholesterolemia
                          • 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 Link_out
                              Multiple sclerosis
                              • 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 Link_out
                                  Associated OMIM IDs
                                  DrugBank ID Not Available
                                  DrugBank Metabolite ID Not Available
                                  Phenol Explorer Compound ID Not Available
                                  Phenol Explorer Metabolite ID Not Available
                                  FoodDB ID FDB022611
                                  KNApSAcK ID Not Available
                                  Chemspider ID 108790 Link_out
                                  KEGG Compound ID C13550 Link_out
                                  BioCyc ID CPD-7239 Link_out
                                  BiGG ID 2197434 Link_out
                                  Wikipedia Link Not Available
                                  NuGOwiki Link HMDB01419 Link_out
                                  Metagene Link HMDB01419 Link_out
                                  METLIN ID Not Available
                                  PubChem Compound 121948 Link_out
                                  PDB ID Not Available
                                  ChEBI ID 34310 Link_out
                                  References
                                  Synthesis Reference Prasad 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 Link_out
                                  2. Lutjohann D, von Bergmann K: 24S-hydroxycholesterol: a marker of brain cholesterol metabolism. Pharmacopsychiatry. 2003 Sep;36 Suppl 2:S102-6. Pubmed: 14574622 Link_out

                                  Enzymes
                                  Name: Cholesterol 24-hydroxylase
                                  Reactions:
                                  Cholesterol + NADPH + Oxygen unknown 24-Hydroxycholesterol + NADP + Water details
                                  Gene Name: CYP46A1
                                  Uniprot ID: Q9Y6A2 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA