3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestane (BioCAD00000004084)

{$topic}

Metabolite Card

Formula: C27H48O3 (420.3603)
SMILES: [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C

Synonyms [en]

5beta-cholestane-3alpha,7alpha,12alpha-triol; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestane; 3alpha,7alpha,12alpha-Trihydroxycoprostane; 3alpha, 7alpha,12alpha-Trihydroxy-5beta-cholestane; 5 beta-cholestane-3 alpha,7 alpha,12 alpha-triol; 5-beta-Cholestane-3-alpha,7-alpha,12-alpha-triol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestane. 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: BioCAD00000004084). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

5beta-Cholestane-3alpha,7alpha,12alpha-triol is an intermediate in bile acid biosynthesis. 5beta-Cholestane-3alpha,7alpha,12alpha-triol is the second to last step in the synthesis of 5beta-cyprinolsulfate. It is converted from 7alpha,12alpha-dihydroxy-5beta-cholestan-3-one via enzymatic reaction, and then it is converted into 3alpha,7alpha,12alpha,26-tetrahydroxy-5beta-cholestane via the enzyme cytochrome P450 (EC 1.14.13.15). This compound inhibits la-hydroxylation (PMID: 7937829). It is the byproduct of cholestanetetraol 26-dehydrogenase (EC 1.1.1.161) and the reaction that catalyzes it is classified as a small molecule reaction (BioCyc).

Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 547-96-6
  • PubChem: 160520
  • PubChem: 21123848
  • ChEBI: ChEBI:16496
  • HMDB: HMDB0001457
  • HMDB: HMDB01457
  • LipidMaps: LMST04030035
  • KEGG: C05454
  • BioCyc: 5-BETA-CHOLESTANE-3-ALPHA7-ALPHA12-ALP
  • NCBI MeSH: 3,7,12-trihydroxycoprostane
  • MoNA: CCMSLIB00005465083
  • MoNA: CCMSLIB00005465084
  • MoNA: CCMSLIB00005465085
  • MoNA: CCMSLIB00005465086
  • MoNA: CCMSLIB00005465087
  • Metlin: METLIN_43050

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R04807 1.14.15.15 C05454 + C00007 + 2 C00080 + 2 C00662<=>C05446 + C00001 + 2 C00667
KEGG:R04824 1.1.1.50 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestane:NAD+ oxidoreductase (B-specific)
KEGG:R04825 1.1.1.50 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestane:NADP+ oxidoreductase (B-specific)
KEGG:R07204 1.14.14.139 5beta-cholestane-3alpha,7alpha-diol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (12alpha-hydroxylating)
KEGG:R11142 1.14.15.15 5beta-cholestane-3alpha,7alpha,12alpha-triol,adrenodoxin:oxygen oxidoreductase (26-hydroxylating)
Rhea:RHEA:14374 5β-cholestane-3α,7α,12α-triol + 2 reduced [adrenodoxin] + O2 + 2 H+ => (25R)-5β-cholestane-3α,7α,12α,26-tetrol + 2 oxidized [adrenodoxin] + H2O
Rhea:RHEA:14375 (25R)-5β-cholestane-3α,7α,12α,26-tetrol + 2 oxidized [adrenodoxin] + H2O => 5β-cholestane-3α,7α,12α-triol + 2 reduced [adrenodoxin] + O2 + 2 H+
Rhea:RHEA:14376 5β-cholestane-3α,7α,12α-triol + 2 reduced [adrenodoxin] + O2 + 2 H+ <=> (25R)-5β-cholestane-3α,7α,12α,26-tetrol + 2 oxidized [adrenodoxin] + H2O
Rhea:RHEA:15262 1.14.14.139 5β-cholestane-3α,7α-diol + reduced [NADPH—hemoprotein reductase] + O2 => 5β-cholestane-3α,7α,12α-triol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:15263 1.14.14.139 5β-cholestane-3α,7α,12α-triol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => 5β-cholestane-3α,7α-diol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:15264 1.14.14.139 5β-cholestane-3α,7α-diol + reduced [NADPH—hemoprotein reductase] + O2 <=> 5β-cholestane-3α,7α,12α-triol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:34632 1.14.15.15 5β-cholestane-3α,7α,12α-triol + 6 reduced [adrenodoxin] + 3 O2 + 5 H+ => (25R)-3α,7α,12α-trihydroxy-5β-cholestan-26-oate + 6 oxidized [adrenodoxin] + 4 H2O
Rhea:RHEA:34633 1.14.15.15 (25R)-3α,7α,12α-trihydroxy-5β-cholestan-26-oate + 6 oxidized [adrenodoxin] + 4 H2O => 5β-cholestane-3α,7α,12α-triol + 6 reduced [adrenodoxin] + 3 O2 + 5 H+
Rhea:RHEA:34634 1.14.15.15 5β-cholestane-3α,7α,12α-triol + 6 reduced [adrenodoxin] + 3 O2 + 5 H+ <=> (25R)-3α,7α,12α-trihydroxy-5β-cholestan-26-oate + 6 oxidized [adrenodoxin] + 4 H2O
Rhea:RHEA:67397 5β-cholestane-3α,7α,12α-triol + reduced [NADPH—hemoprotein reductase] + O2 => 5β-cholestane-3α,7α,12α,25-tetrol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:67398 5β-cholestane-3α,7α,12α,25-tetrol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => 5β-cholestane-3α,7α,12α-triol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:67399 5β-cholestane-3α,7α,12α-triol + reduced [NADPH—hemoprotein reductase] + O2 <=> 5β-cholestane-3α,7α,12α,25-tetrol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
BioCyc:1.14.13.96-RXN 1.14.14.139 CPD-7238 + Red-NADPH-Hemoprotein-Reductases + OXYGEN-MOLECULE --> 5-BETA-CHOLESTANE-3-ALPHA7-ALPHA12-ALP + Ox-NADPH-Hemoprotein-Reductases + WATER
BioCyc:RXN-13690 1.14.15.15 5-BETA-CHOLESTANE-3-ALPHA7-ALPHA12-ALP + 6 Reduced-adrenal-ferredoxins + 5 PROTON + 3 OXYGEN-MOLECULE --> CPD-1836 + 6 Oxidized-adrenal-ferredoxins + 4 WATER
BioCyc:CHOLESTANETRIOL-26-MONOOXYGENASE-RXN 5-BETA-CHOLESTANE-3-ALPHA7-ALPHA12-ALP + 2 Reduced-adrenal-ferredoxins + 2 PROTON + OXYGEN-MOLECULE --> 5-BETA-CHOLESTANE-3-ALPHA7-TETRAOL + 2 Oxidized-adrenal-ferredoxins + WATER
View More
Organism Source

Taxonomy Source

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-CEL-194068 Bile acid and bile salt metabolism
Reactome:R-CFA-1430728 Metabolism
Reactome:R-CFA-556833 Metabolism of lipids
Reactome:R-CFA-194068 Bile acid and bile salt metabolism
Reactome:R-DRE-193368 Synthesis of bile acids and bile salts via 7alpha-hydroxycholesterol
Reactome:R-DDI-192105 Synthesis of bile acids and bile salts
Reactome:R-DME-194068 Bile acid and bile salt metabolism
Reactome:R-HSA-194068 Bile acid and bile salt metabolism
Reactome:R-HSA-1643685 Disease
Reactome:R-MMU-1430728 Metabolism
Reactome:R-MMU-556833 Metabolism of lipids
Reactome:R-MMU-8957322 Metabolism of steroids
Reactome:R-RNO-193368 Synthesis of bile acids and bile salts via 7alpha-hydroxycholesterol
Reactome:R-SCE-8957322 Metabolism of steroids
Reactome:R-SCE-194068 Bile acid and bile salt metabolism
Reactome:R-SPO-1430728 Metabolism
View All Pathways