4alpha-Hydroxymethyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol (BioCAD00000025190)

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Metabolite Card

Formula: C29H50O2 (430.3811)
SMILES: CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(CO)C1CC3

Synonyms [en]

4a-Hydroxymethyl-4b-methyl-5a-cholesta-8-en-3b-ol; 4a-Hydroxymethyl-4beta-methyl-5a-cholesta-8-en-3beta-ol; 4alpha-Hydroxymethyl-4b-methyl-5alpha-cholesta-8-en-3b-ol; 4Α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol; (2S,5S,6R,15R)-6-(hydroxymethyl)-2,6,15-trimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol; 4\u03b1-hydroxymethyl-4\u03b2-methyl-5\u03b1-cholesta-8-en-3\u03b2-ol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

4alpha-Hydroxymethyl-4beta-methyl-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: BioCAD00000025190). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

4alpha-hydroxymethyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic reduction of 4alpha-formyl-4beta-methyl-5alpha-cholesta-8-en-3beta-ol or from the enzymatic oxidation of 4,4-dimethyl-5alpha-cholesta-8-en-3-beta-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
  • PubChem: 25203709
  • ChEBI: ChEBI:87045
  • HMDB: HMDB0012171
  • LipidMaps: LMST01010233
  • BioCyc: CPD-8611
  • Coconut NaturalProduct: CNP0090869.1

Class / Ontology

Metabolic Network
ID EC Number Name
Rhea:RHEA:46817 4,4-dimethyl-5α-cholest-8-en-3β-ol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ => 4α-hydroxymethyl-4β-methyl-5α-cholest-8-en-3β-ol + 2 Fe(III)-[cytochrome b5] + H2O
Rhea:RHEA:46818 4α-hydroxymethyl-4β-methyl-5α-cholest-8-en-3β-ol + 2 Fe(III)-[cytochrome b5] + H2O => 4,4-dimethyl-5α-cholest-8-en-3β-ol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+
Rhea:RHEA:46819 4,4-dimethyl-5α-cholest-8-en-3β-ol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ <=> 4α-hydroxymethyl-4β-methyl-5α-cholest-8-en-3β-ol + 2 Fe(III)-[cytochrome b5] + H2O
Rhea:RHEA:46821 4α-hydroxymethyl-4β-methyl-5α-cholest-8-en-3β-ol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ => 4α-hydroxyformyl-4β-methyl-5α-cholest-8-en-3β-ol + 2 Fe(III)-[cytochrome b5] + 2 H2O
Rhea:RHEA:46822 4α-hydroxyformyl-4β-methyl-5α-cholest-8-en-3β-ol + 2 Fe(III)-[cytochrome b5] + 2 H2O => 4α-hydroxymethyl-4β-methyl-5α-cholest-8-en-3β-ol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+
Rhea:RHEA:46823 4α-hydroxymethyl-4β-methyl-5α-cholest-8-en-3β-ol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ <=> 4α-hydroxyformyl-4β-methyl-5α-cholest-8-en-3β-ol + 2 Fe(III)-[cytochrome b5] + 2 H2O
BioCyc:RXN66-15 4,4-dimethyl-5α-cholesta-8-en-3-β-ol 4-hydroxylase
BioCyc:RXN66-16 4α-hydroxymethyl-4β-methyl-5α-cholesta-8-en-3β-ol 4-dehydrogenase
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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)
PathBank:SMP0121060 Kandutsch-Russell Pathway (Cholesterol Biosynthesis)
View All Pathways