3alpha,7alpha-Dihydroxy-5beta-cholestane (BioCAD00000004080)

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Metabolite Card

Formula: C27H48O2 (404.3654)
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])CC[C@]12C)[C@H](C)CCCC(C)C

Synonyms [en]

5beta-cholestane-3alpha,7alpha-diol; 3alpha,7alpha-Dihydroxy-5beta-cholestane; dihydroxycoprostane; dihydroxycoprostane, (3beta,5alpha,7alpha)-isomer; 5alpha-Cholestane-3beta,7beta-diol; 3,7-dihydroxycholestane

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

3alpha,7alpha-Dihydroxy-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: BioCAD00000004080). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

3alpha,7alpha-Dihydroxy-5beta-cholestane is an intermediate in bile acid synthesis. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487, 16037564, 12576301, 11907135).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 3862-26-8
  • PubChem: 3080603
  • ChEBI: ChEBI:28047
  • HMDB: HMDB0006893
  • HMDB: HMDB06893
  • LipidMaps: LMST04030109
  • KEGG: C05452
  • BioCyc: CPD-7238
  • NCBI MeSH: dihydroxycoprostane
  • RefMet: RM0126120
  • Metlin: METLIN_43113
  • Coconut NaturalProduct: CNP0245981.1

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R04806 1.14.15.15 C05452 + C00007 + 2 C00080 + 2 C00662<=>C05444 + C00001 + 2 C00667
KEGG:R04818 1.1.1.50 3alpha,7alpha-dihydroxy-5beta-cholestane:NAD+ oxidoreductase (B-specific)
KEGG:R04819 1.1.1.50 3alpha,7alpha-dihydroxy-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)
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:67385 5β-cholestane-3α,7α-diol + reduced [NADPH—hemoprotein reductase] + O2 => 5β-cholestane-3α,7α,25-triol + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:67386 5β-cholestane-3α,7α,25-triol + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => 5β-cholestane-3α,7α-diol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:67387 5β-cholestane-3α,7α-diol + reduced [NADPH—hemoprotein reductase] + O2 <=> 5β-cholestane-3α,7α,25-triol + 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-9842 5β-cholestane-3α,7α-diol 26-hydroxylase
BioCyc:RXN-13713 1.14.15.15 5β-cholestane-3α,7α-diol 26-monooxygenase
BioCyc:RXN-9841 1.1.1.213 5β-cholestane-3α,7α-diol 3-dehydrogenase
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
BioCyc:MOUSE_PWY-6061 bile acid biosynthesis, neutral pathway
PlantCyc:CORKOAK_PWY-5129 sphingolipid biosynthesis (plants)
PlantCyc:CARIETINUM_ICC4958_PWY-5129 sphingolipid biosynthesis (plants)
PlantCyc:RMULTIFLORA_PWY-5129 sphingolipid biosynthesis (plants)
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-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
View All Pathways