Cerebrosterol (BioCAD00000008229)
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
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.
DBLinks
- CAS Registry Number: 474-73-7
- PubChem CID: 121948
- ChEBI: 34310
- HMDB: HMDB0001419
- LipidMaps: LMST01010019
- KEGG: C13550
- BioCyc: CPD-7239
- NCBI MeSH: 24-hydroxycholesterol
- Wikipedia: 24S-Hydroxycholesterol
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
- WishartLab ClassyFire: [Bile acids, alcohols and derivatives] Bile acids, alcohols and derivatives
- RefMet: [Cholesterols] Cholesterols
- LipidMaps: [Cholesterol and derivatives [ST0101]] Cholesterol and derivatives [ST0101]
- ChEBI: [CHEBI:34310] (24S)-24-hydroxycholesterol
- Coconut NaturalProduct: [Cholestane steroids] Cholestane steroids
| 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+ |
Taxonomy Source
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 |