7alpha-Hydroxycholesterol (BioCAD00000005478)

blood cerebrospinal fluid (csf) feces placenta plant natural products

Metabolite Card

Formula: C27H46O2 (402.3498)
SMILES: [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

Synonyms [en]

7alpha-hydroxycholesterol; 7alpha-hydroxy-cholesterol; Cholest-5-ene-3beta,7alpha-diol; Cholest-5-en-3beta,7alpha-diol; (3beta,7alpha)-cholest-5-ene-3,7-diol; 7-alpha-Hydroxycholesterol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

7alpha-Hydroxycholesterol. 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: BioCAD00000005478). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

7alpha-Hydroxycholesterol is an oxysterol and can serve as a biomarker for lipid peroxidation (PMID: 17386651). Products of cholesterol oxidation accumulate within atherosclerotic plaque and have been proposed to contribute to inflammatory signalling in the diseased artery (PMID: 17364953). 7alpha-Hydroxycholesterol is a cholesterol oxide that has been described as a biomarker of oxidative stress in subjects with impaired glucose tolerance and diabetes (PMID: 16634125). 7alpha-Hydroxycholesterol has been identified in the human placenta (PMID: 32033212).

Extracellular Membrane Endoplasmic reticulum
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 566-26-7
  • PubChem: 107722
  • ChEBI: ChEBI:17500
  • HMDB: HMDB0001496
  • HMDB: HMDB01496
  • LipidMaps: LMST01010013
  • KEGG: C03594
  • BioCyc: CPD-266
  • NCBI MeSH: cholest-5-en-3 beta,7 alpha-diol
  • Wikipedia: 7%CE%B1-Hydroxycholesterol
  • Wikipedia: 7α-Hydroxycholesterol
  • RefMet: RM0138886
  • MoNA: CCMSLIB00005466004
  • MoNA: CCMSLIB00005466005
  • MoNA: CCMSLIB00005466006
  • MoNA: CCMSLIB00005466007
  • Metlin: METLIN_3896
  • Coconut NaturalProduct: CNP0118361.1
  • Coconut NaturalProduct: CNP0147119.3
  • Coconut NaturalProduct: CNP0147119.4
  • Coconut NaturalProduct: CNP0503190.1
  • Coconut NaturalProduct: CNP0503190.2
  • Coconut NaturalProduct: CNP0503190.3
  • Coconut NaturalProduct: CNP0503190.4

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01463 1.14.14.23 cholesterol,NADPH-hemoprotein reductase:oxygen oxidoreductase (7alpha-hydroxylating)
KEGG:R04263 1.1.1.181 7alpha-hydroxycholesterol:NAD+ 3-oxidoreductase
KEGG:R04264 1.1.1.181 cholest-5-ene-3beta,7alpha-diol:NAD+ 3-oxidoreductase
Rhea:RHEA:11897 1.1.1.181 7α-hydroxycholesterol + NAD+ => 7α-hydroxycholest-4-en-3-one + NADH + H+
Rhea:RHEA:11898 1.1.1.181 7α-hydroxycholest-4-en-3-one + NADH + H+ => 7α-hydroxycholesterol + NAD+
Rhea:RHEA:11899 1.1.1.181 7α-hydroxycholesterol + NAD+ <=> 7α-hydroxycholest-4-en-3-one + NADH + H+
Rhea:RHEA:21813 1.14.14.23 cholesterol + reduced [NADPH—hemoprotein reductase] + O2 => 7α-hydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:21814 1.14.14.23 7α-hydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => cholesterol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:21815 1.14.14.23 cholesterol + reduced [NADPH—hemoprotein reductase] + O2 <=> 7α-hydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:46381 7α-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2 => (24S)-7α-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:46382 (24S)-7α-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => 7α-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:46383 7α-hydroxycholesterol + reduced [NADPH—hemoprotein reductase] + O2 <=> (24S)-7α-dihydroxycholesterol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:68741 7-oxocholesterol + NADPH + H+ => 7α-hydroxycholesterol + NADP+
Rhea:RHEA:68742 7α-hydroxycholesterol + NADP+ => 7-oxocholesterol + NADPH + H+
Rhea:RHEA:68743 7-oxocholesterol + NADPH + H+ <=> 7α-hydroxycholesterol + NADP+
BioCyc:CHOLESTEROL-7-ALPHA-MONOOXYGENASE-RXN 1.14.14.23 CHOLESTEROL + Red-NADPH-Hemoprotein-Reductases + OXYGEN-MOLECULE --> CPD-266 + Ox-NADPH-Hemoprotein-Reductases + WATER
BioCyc:1.1.1.181-RXN 1.1.1.181 CPD-266 + NAD --> CPD-1087 + NADH + PROTON
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Organism Source

Taxonomy Source

  1. Myrtillocactus geometrizans [ncbi taxid: 336127]
  2. Peniocereus fosterianus [ncbi taxid: 336130]
  3. Stenocereus thurberi [ncbi taxid: 171973]
  4. Chelidonium majus [ncbi taxid: 71251]
  5. Homo sapiens [ncbi taxid: 9606]
  6. Mus musculus [ncbi taxid: 10090]

Pathway Synthetic

pathway id name
BioCyc:MOUSE_PWY-6061 bile acid biosynthesis, neutral pathway
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-193368 Synthesis of bile acids and bile salts via 7alpha-hydroxycholesterol
Reactome:R-DRE-211897 Cytochrome P450 - arranged by substrate type
Reactome:R-DME-194068 Bile acid and bile salt metabolism
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-211859 Biological oxidations
View All Pathways