4,4-Dimethyl-14alpha-formyl-5alpha-cholesta-8-en-3beta-ol (BioCAD00000025181)

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Metabolite Card

Formula: C30H50O2 (442.3811)
SMILES: CC(C)CCCC(C)C1CC[C@@]2(C=O)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3

Synonyms [en]

4,4-Dimethyl-14alpha-formyl-5alpha-cholesta-8-en-3beta-ol; 4,4-Dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol; 4,4-dimethyl-14alpha-formyl-5alpha-cholest-8-en-3beta-ol; 4,4-Dimethyl-14alpha-formyl-5alpha-cholesta-8-en-3-beta-ol; Lanosten-3-ol-32-al; 4,4-Dimethyl-14alpha-formyl-5alpha-cholesta-8-en-3 beta-ol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

4,4-Dimethyl-14alpha-formyl-5alpha-cholesta-8-en-3beta-ol. 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: BioCAD00000025181). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

4, 4-Dimethyl-14alpha-formyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis. It is a substrate for lanosterol 14alpha-demethylase (CYP51A1) and can be generated from the enzymatic oxidation of 4,4-dimethyl-14alpha-hydroxymethyl-5alpha-cholesta-8-en-3beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 59200-40-7
  • PubChem: 25203343
  • ChEBI: ChEBI:87060
  • HMDB: HMDB0012159
  • LipidMaps: LMST01010223
  • BioCyc: CPD-8608

Class / Ontology

Metabolic Network
ID EC Number Name
Rhea:RHEA:75084 32-oxo-24,25-dihydrolanosterol + reduced [NADPH—hemoprotein reductase] + O2 => 4,4-dimethyl-8,14-cholestadien-3β-ol + formate + oxidized [NADPH—hemoprotein reductase] + H2O + 2 H+
Rhea:RHEA:75085 4,4-dimethyl-8,14-cholestadien-3β-ol + formate + oxidized [NADPH—hemoprotein reductase] + H2O + 2 H+ => 32-oxo-24,25-dihydrolanosterol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:75086 32-oxo-24,25-dihydrolanosterol + reduced [NADPH—hemoprotein reductase] + O2 <=> 4,4-dimethyl-8,14-cholestadien-3β-ol + formate + oxidized [NADPH—hemoprotein reductase] + H2O + 2 H+
Rhea:RHEA:75088 32-hydroxy-24,25-dihydrolanosterol + reduced [NADPH—hemoprotein reductase] + O2 => 32-oxo-24,25-dihydrolanosterol + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+
Rhea:RHEA:75089 32-oxo-24,25-dihydrolanosterol + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+ => 32-hydroxy-24,25-dihydrolanosterol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:75090 32-hydroxy-24,25-dihydrolanosterol + reduced [NADPH—hemoprotein reductase] + O2 <=> 32-oxo-24,25-dihydrolanosterol + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+
BioCyc:RXN66-12 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol 14-dehydrogenase
BioCyc:RXN66-13 4,4-dimethyl-14α-formyl-5α-cholesta-8-en-3β-ol deformylase
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
BioCyc:MOUSE_PWY66-3 cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
BioCyc:THAPS_PWY66-5 superpathway of cholesterol biosynthesis
BioCyc:SMAN_PWY66-5 superpathway of cholesterol biosynthesis
BioCyc:PCHR_PWY66-3 cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
BioCyc:THAPS_PWY66-3 cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
BioCyc:SMAN_PWY66-3 cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
View All Pathways