7alpha-Hydroxycholest-4-en-3-one (BioCAD00000005477)

blood urine liver

Metabolite Card

Formula: C27H44O2 (400.3341)
SMILES: [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

Synonyms [en]

7alpha-Hydroxycholest-4-en-3-one; 7alpha-Hydroxy-4-cholesten-3-one; Cholest-4-en-7alpha-ol-3-one; 7 alpha-3ox-C; 7-hydroxy-4-cholesten-3-one; 7a-Hydroxy-4-cholesten-3-one-12alpha

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

7alpha-Hydroxycholest-4-en-3-one. 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: BioCAD00000005477). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

7a-Hydroxy-cholestene-3-one is a metabolite in bile acid synthesis. It is derived from 7a-hydroxy-cholesterol and can be further metabolized to 7a,12a,-dihydroxy-cholest-4-en-3-one. Analysis of 7a-Hydroxycholestene-3-one (HCO) in serum may serve as a novel, simple, and sensitive method for the detection of bile acid malabsorption in patients with chronic diarrhea of unknown origin (PMID 9952217).

Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 3862-25-7
  • PubChem: 123743
  • ChEBI: ChEBI:17899
  • HMDB: HMDB0001993
  • HMDB: HMDB01993
  • LipidMaps: LMST04030123
  • KEGG: C05455
  • BioCyc: CPD-1087
  • NCBI MeSH: 7 alpha-hydroxy-4-cholesten-3-one
  • Wikipedia: 7%CE%B1-Hydroxy-4-cholesten-3-one
  • RefMet: RM0128379
  • MoNA: CCMSLIB00005465954
  • MoNA: CCMSLIB00005465955
  • MoNA: CCMSLIB00005465956
  • MoNA: CCMSLIB00005465957
  • MoNA: CCMSLIB00005465958
  • Metlin: METLIN_43126
  • Coconut NaturalProduct: CNP0111476.1

Class / Ontology

Metabolic Network
ID EC Number Name
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
KEGG:R04817 1.3.1.3 7alpha-hydroxy-5beta-cholestan-3-one:NADP+ delta4-oxidoreductase
KEGG:R04826 1.14.14.139 7alpha-hydroxycholest-4-en-3-one,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (12alpha-hydroxylating)
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:46641 7α-hydroxycholest-4-en-3-one + NADPH + H+ => 7α-hydroxy-5β-cholestan-3-one + NADP+
Rhea:RHEA:46642 7α-hydroxy-5β-cholestan-3-one + NADP+ => 7α-hydroxycholest-4-en-3-one + NADPH + H+
Rhea:RHEA:46643 7α-hydroxycholest-4-en-3-one + NADPH + H+ <=> 7α-hydroxy-5β-cholestan-3-one + NADP+
Rhea:RHEA:46753 1.14.14.139 7α-hydroxycholest-4-en-3-one + reduced [NADPH—hemoprotein reductase] + O2 => 7α,12α-dihydroxycholest-4-en-3-one + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:46754 1.14.14.139 7α,12α-dihydroxycholest-4-en-3-one + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => 7α-hydroxycholest-4-en-3-one + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:46755 1.14.14.139 7α-hydroxycholest-4-en-3-one + reduced [NADPH—hemoprotein reductase] + O2 <=> 7α,12α-dihydroxycholest-4-en-3-one + oxidized [NADPH—hemoprotein reductase] + H2O + H+
BioCyc:RXN-9840 1.3.1.3 CPD-1087 + NADPH + PROTON --> CPD-10548 + NADP
BioCyc:1.1.1.181-RXN 1.1.1.181 CPD-266 + NAD --> CPD-1087 + NADH + PROTON
BioCyc:1.14.13.95-RXN 1.14.14.139 CPD-1087 + Red-NADPH-Hemoprotein-Reductases + OXYGEN-MOLECULE --> CPD-7237 + Ox-NADPH-Hemoprotein-Reductases + WATER
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Organism Source

Taxonomy Source

  1. Dendronephthya gigantea [ncbi taxid: 151771]
  2. Homo sapiens [ncbi taxid: 9606]
  3. 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-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-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-DDI-192105 Synthesis of bile acids and bile salts
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-HSA-211994 Sterols are 12-hydroxylated by CYP8B1
Reactome:R-MMU-1430728 Metabolism
Reactome:R-MMU-556833 Metabolism of lipids
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