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Human Metabolome Database Version 2.5

 

Showing metabocard for 24-Hydroxycholesterol (HMDB01419)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-16 15:44:11
Update Date 2009-05-05 20:58:46
Accession Number HMDB01419
Secondary Accession Numbers Not Available
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, 14574622)
Synonyms
  1. (24S)-24-Hydroxycholesterol
  2. 24(S)-Hydroxycholesterol
  3. 24-Hydroxycholesterol
  4. 24S-Cholest-5-ene-3b,24-diol
  5. Cerebrosterin
  6. Cerebrosterol
  7. Cholest-5-ene-3b,24b-diol
  8. 24S-hydroxycholesterol
  9. (24S)-cholest-5-ene-3b,24-diol
  10. (24S)-cholest-5-ene-3beta,24-diol
  11. Cholest-5-ene-3,24-diol
  12. Cholest-5-en-3b,24S-diol
  13. Cholest-5-en-3beta,24S-diol
Chemical IUPAC Name (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-hydroxy-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Chemical Formula C27H46O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Dihydroxy steroids
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • alkene
Biofunction
  • Hormones, Membrane component
Application
—
Source
  • Endogenous
Average Molecular Weight 402.653
Monoisotopic Molecular Weight 402.349792
Isomeric SMILES CC(C)[C@@H](O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Canonical SMILES CC(C)C(O)CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C
KEGG Compound ID C13550 Link Image
BioCyc ID CPD-7239 Link Image
BiGG ID 2197434 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB01419 Link Image
Metagene Link HMDB01419 Link Image
METLIN ID Not Available
PubChem Compound 121948 Link Image
PubChem Substance 7846926 Link Image
ChEBI ID 34310 Link Image
CAS Registry Number 474-73-7
InChI Identifier InChI=1/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
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.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 4.03e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 6.5 [Predicted by PubChem via XLOGP]; 5.70 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • endoplasmic reticulum
Biofluid Location
  • Blood
  • Cerebrospinal Fluid
Tissue Location Not Available
Concentrations (Normal)
Biofluid Blood
Value 0.0018 +/- 0.00052 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Holdenrieder S, Lutjohann D, Geiger S, von Bergmann K, Stieber P, Hamann GF: Does brain specific 24S-hydroxycholesterol in plasma indicate the disruption of the blood-brain barrier in patients with ischemic stroke? Neurosci Lett. 2004 Sep 23;368(2):201-4. [PubMed Link Image]
Biofluid CSF
Value 0.0034 (0.0033-0.0036) uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Concentrations (Abnormal)
Biofluid Blood
Value 0.11 +/- 0.03 uM
Age Adult:>18 yrs old
Sex N/A
Condition Hypercholesterolemia
Comments Moderately elevated plasma cholesterol levels
References
  • 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 Link Image]
Biofluid CSF
Value 0.0061 (0.0058-0.0064) uM
Age Elderly:>65 yrs old
Sex Both
Condition Alzheimer's disease
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.016 (0.014-0.017) uM
Age Adult:>18 yrs old
Sex Both
Condition Demyelinating polyneuropathy
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.0045 (0.0041-0.0050) uM
Age Adult:>18 yrs old
Sex Both
Condition Subarachnoid hemorrhage
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.0086 (0.0076-0.0096) uM
Age Adult:>18 yrs old
Sex Both
Condition Meningitis
Comments Viral
References
  • 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 Link Image]
Biofluid CSF
Value 0.0062 (0.0057-0.0068) uM
Age Adult:>18 yrs old
Sex Both
Condition Neuroborreliosis
Comments Not Available
References
  • 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 Link Image]
Biofluid CSF
Value 0.0077 (0.0066-0.0093) uM
Age Adult:>18 yrs old
Sex N/A
Condition Mild cognitive impairment
Comments Also known as incipient dementia or isolated memory impairment
References
  • 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 Link Image]
Biofluid CSF
Value 0.004 +/- 0.0013 uM
Age Adult:>18 yrs old
Sex Both
Condition Multiple sclerosis
Comments Not Available
References
  • 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 Link Image]
Associated Disorders
Condition 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 Link Image]
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 Link Image]
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 Link Image]
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 Link Image]
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 Link Image]
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 Link Image]
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 Link Image]
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 Link Image]
OMIM ID
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 Link Image map00120 Link Image
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 Link Image]
Metabolic Enzymes
  1. Cytochrome P450, family 39, subfamily A, polypeptide 1
  2. Cytochrome P450 46A1
Enzyme 1 [top]
Enzyme 1 ID 8685
Enzyme 1 Name Cytochrome P450, family 39, subfamily A, polypeptide 1
Enzyme 1 Synonyms Not Available
Enzyme 1 Gene Name CYP39A1
Enzyme 1 Protein Sequence >Cytochrome P450, family 39, subfamily A, polypeptide 1 
MELISPTVIIILGCLALFLLLQRKNLRRPPCIKGWIPWIGVGFEFGKAPLEFIEKARIKY
GPIFTVFAMGNRMTFVTEEEGINVFLKSKKVDFELAVQNIVYRTASIPKNVFLALHEKLY
IMLKGKMGTVNLHQFTGQLTEELHEQLENLGTHGTMDLNNLVRHLLYPVTVNMLFNKSLF
STNKKKIKEFHQYFQVYDEDFEYGSQLPECLLRNWSKSKKWFLELFEKNIPDIKACKSAK
DNSMTLLQATLDIVETETSKENSPNYGLLLLWASLSNAVPVAFWTLAYVLSHPDIHKAIM
EGISSVFGKAGKDKIKVSEDDLENLLLIKWCVLETIRLKAPGVITRKVVKPVEILNYIIP
SGDLLMLSPFWLHRNPKYFPEPELFKPERWKKANLEKHSFLDCFMAFGSGKFQCPARWFA
LLEVQMCIILILYKYDCSLLDPLPKQSYLHLVGVPQPEGQCRIEYKQRI
Enzyme 1 Number of Residues 469
Enzyme 1 Molecular Weight 54116
Enzyme 1 Theoretical pI 8.88
Enzyme 1 GO Classification
Function
  • binding
  • catalytic activity
  • cation binding
  • heme binding
  • ion binding
  • iron ion binding
  • monooxygenase activity
  • oxidoreductase activity
  • tetrapyrrole binding
  • transition metal ion binding
Process
  • cellular metabolism
  • electron transport
  • generation of precursor metabolites and energy
  • metabolism
  • physiological process
Component
—
Enzyme 1 General Function Secondary metabolites biosynthesis, transport and catabolism
Enzyme 1 Specific Function Not Available
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • 1-26
Enzyme 1 Transmembrane Regions
  • 4-21
  • 268-290
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 55665524 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q5VTT0 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name Q5VTT0_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >313 bp 
ATGGAACTAATTTCCCCAACAGTGATTATAATCCTGGGTTGCCTTGCTCTGTTCTTACTC
CTTCAGCGGAAGAATTTGCGTAGACCCCCGTGCATCAAGGGCTGGATTCCTTGGATTGGA
GTTGGATTTGAGTTTGGGAAAGCCCCTCTAGAATTTATAGAGAAAGCAAGAATCAAGTAT
GGACCAATATTTACAGTCTTTGCTATGGGAAACCGAATGACCTTTGTTACTGAAGAAGAA
GGAATTAATGTGTTTCTAAAATCCAAAAAAGTAGATTTTGAACTAGCAGTGCAAAATATC
GTTTATCGTACAG
Enzyme 1 GenBank Gene ID AL591242 Link Image
Enzyme 1 GeneCard ID CYP39A1 Link Image
Enzyme 1 GenAtlas ID CYP39A1 Link Image
Enzyme 1 HGNC ID HGNC:17449 Link Image
Enzyme 1 Chromosome Location 6
Enzyme 1 Locus 6p21.1-p11.2
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References Not Available
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 10660
Enzyme 2 Name Cytochrome P450 46A1
Enzyme 2 Synonyms
  1. Cholesterol 24-hydroxylase
  2. CH24H
Enzyme 2 Gene Name CYP46A1
Enzyme 2 Protein Sequence >Cytochrome P450 46A1 
MSPGLLLLGSAVLLAFGLCCTFVHRARSRYEHIPGPPRPSFLLGHLPCFWKKDEVGGRVL
QDVFLDWAKKYGPVVRVNVFHKTSVIVTSPESVKKFLMSTKYNKDSKMYRALQTVFGERL
FGQGLVSECNYERWHKQRRVIDLAFSRSSLVSLMETFNEKAEQLVEILEAKADGQTPVSM
QDMLTYTAMDILAKAAFGMETSMLLGAQKPLSQAVKLMLEGITASRNTLAKFLPGKRKQL
REVRESIRFLRQVGRDWVQRRREALKRGEEVPADILTQILKAEEGAQDDEGLLDNFVTFF
IAGHETSANHLAFTVMELSRQPEIVARLQAEVDEVIGSKRYLDFEDLGRLQYLSQVLKES
LRLYPPAWGTFRLLEEETLIDGVRVPGNTPLLFSTYVMGRMDTYFEDPLTFNPDRFGPGA
PKPRFTYFPFSLGHRSCIGQQFAQMEVKVVMAKLLQRLEFRLVPGQRFGLQEQATLKPLD
PVLCTLRPRGWQPAPPPPPC
Enzyme 2 Number of Residues 500
Enzyme 2 Molecular Weight 56822
Enzyme 2 Theoretical pI Not Available
Enzyme 2 GO Classification
Function
  • binding
  • catalytic activity
  • cation binding
  • heme binding
  • ion binding
  • iron ion binding
  • monooxygenase activity
  • oxidoreductase activity
  • tetrapyrrole binding
  • transition metal ion binding
Process
  • cellular metabolism
  • electron transport
  • generation of precursor metabolites and energy
  • metabolism
  • physiological process
Component
—
Enzyme 2 General Function Secondary metabolites biosynthesis, transport and catabolism
Enzyme 2 Specific Function Involved in the turnover of cholesterol. It converts cholesterol into 24S-hydroxycholesterol and, to a lesser extent, 25-hydroxycholesterol
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions
  • Cholesterol + H+ + Nicotinamide adenine dinucleotide phosphate - reduced + O2 --> H2O + Nicotinamide adenine dinucleotide phosphate + 24-Hydroxycholesterol
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • 3-23
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 5257114 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q9Y6A2 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name CP46A_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence Not Available
Enzyme 2 GenBank Gene ID AF094480 Link Image
Enzyme 2 GeneCard ID Not Available
Enzyme 2 GenAtlas ID CYP46A1 Link Image
Enzyme 2 HGNC ID HGNC:2641 Link Image
Enzyme 2 Chromosome Location Not Available
Enzyme 2 Locus Not Available
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References
  1. Lund EG, Guileyardo JM, Russell DW: cDNA cloning of cholesterol 24-hydroxylase, a mediator of cholesterol homeostasis in the brain. Proc Natl Acad Sci U S A. 1999 Jun 22;96(13):7238-43. [PubMed Link Image]
Enzyme 2 Metabolite References Not Available