Cerebrosterol (BioCAD00000008229)

blood cerebrospinal fluid (csf) feces

Metabolite Card

Formula: C27H46O2 (402.3498)
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

Synonyms [en]

cerebrosterol; 24S-hydroxy-cholesterol; (24S)-24-Hydroxycholesterol; cholest-5-en-3beta,24S-diol; 24(S)-hydroxycholesterol; (24S)-cholest-5-ene-3beta,24-diol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Cerebrosterol. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000008229). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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). 24-Hydroxycholesterol has been found to accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 474-73-7
  • PubChem: 121948
  • PubChem: 12302757
  • ChEBI: ChEBI:34310
  • ChEBI: ChEBI:50515
  • HMDB: HMDB0001419
  • LipidMaps: LMST01010019
  • KEGG: C13550
  • BioCyc: CPD-7239
  • NCBI MeSH: 24-hydroxycholesterol
  • Wikipedia: 24S-Hydroxycholesterol
  • RefMet: RM0135646
  • Metlin: METLIN_3900
  • Coconut NaturalProduct: CNP0043327.1
  • Coconut NaturalProduct: CNP0043327.2
  • Coconut NaturalProduct: CNP0043327.3
  • Coconut NaturalProduct: CNP0043327.4
  • Coconut NaturalProduct: CNP0043327.5
  • Coconut NaturalProduct: CNP0043327.6
  • Coconut NaturalProduct: CNP0043327.7
  • Coconut NaturalProduct: CNP0043327.8
  • Coconut NaturalProduct: CNP0243371.1

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R07207 1.14.14.25 cholesterol,NADPH-hemoprotein reductase:oxygen oxidoreductase (24-hydroxylating)
KEGG:R07208 1.14.14.26 (24S)-cholest-5-ene-3beta,24-diol,NADPH-hemoprotein reductase:oxygen oxidoreductase (7alpha-hydroxylating)
Rhea:RHEA:22717 1.14.14.25 cholesterol + reduced [NADPH—hemoprotein reductase] + O2 => (24S)-hydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:22718 1.14.14.25 (24S)-hydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => cholesterol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:22719 1.14.14.25 cholesterol + reduced [NADPH—hemoprotein reductase] + O2 <=> (24S)-hydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:43217 a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholine + (24S)-hydroxycholesterol => (24S)-24-hydroxycholesterol ester + 1-hexadecanoyl-sn-glycero-3-phosphocholine
Rhea:RHEA:43218 (24S)-24-hydroxycholesterol ester + 1-hexadecanoyl-sn-glycero-3-phosphocholine => a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholine + (24S)-hydroxycholesterol
Rhea:RHEA:43219 a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholine + (24S)-hydroxycholesterol <=> (24S)-24-hydroxycholesterol ester + 1-hexadecanoyl-sn-glycero-3-phosphocholine
Rhea:RHEA:43225 (24S)-hydroxycholesterol + 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine => (24S)-hydroxycholesterol 3-linoleoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine
Rhea:RHEA:43226 (24S)-hydroxycholesterol 3-linoleoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine => (24S)-hydroxycholesterol + 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:43227 (24S)-hydroxycholesterol + 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine <=> (24S)-hydroxycholesterol 3-linoleoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine
Rhea:RHEA:46125 1.14.14.26 (24S)-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2 => (24S)-7α-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:46126 1.14.14.26 (24S)-7α-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => (24S)-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:46127 1.14.14.26 (24S)-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2 <=> (24S)-7α-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:46385 (24S)-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2 => 24S,25-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:46386 24S,25-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => (24S)-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:46387 (24S)-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2 <=> 24S,25-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:46389 (24S)-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2 => (24S,25R)-24,26-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:46390 (24S,25R)-24,26-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => (24S)-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:46391 (24S)-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2 <=> (24S,25R)-24,26-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
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Organism Source

Taxonomy Source

  1. Homo sapiens [ncbi taxid: 9606]

Pathway Synthetic

pathway id name
Reactome:R-BTA-1430728 Metabolism
Reactome:R-BTA-556833 Metabolism of lipids
Reactome:R-BTA-194068 Bile acid and bile salt metabolism
Reactome:R-BTA-211945 Phase I - Functionalization of compounds
Reactome:R-CFA-1430728 Metabolism
Reactome:R-CFA-556833 Metabolism of lipids
Reactome:R-CFA-194068 Bile acid and bile salt metabolism
Reactome:R-CFA-211976 Endogenous sterols
Reactome:R-DRE-211897 Cytochrome P450 - arranged by substrate type
Reactome:R-GGA-194068 Bile acid and bile salt metabolism
Reactome:R-GGA-211976 Endogenous sterols
Reactome:R-HSA-194068 Bile acid and bile salt metabolism
Reactome:R-HSA-211859 Biological oxidations
Reactome:R-MMU-1430728 Metabolism
Reactome:R-MMU-556833 Metabolism of lipids
Reactome:R-MMU-8957322 Metabolism of steroids
Reactome:R-MMU-193775 Synthesis of bile acids and bile salts via 24-hydroxycholesterol
Reactome:R-MMU-211859 Biological oxidations
Reactome:R-RNO-211945 Phase I - Functionalization of compounds
Reactome:R-SSC-211945 Phase I - Functionalization of compounds
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