3-Keto-4-methylzymosterol (BioCAD00000003611)

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Metabolite Card

Formula: C28H44O (396.3392)
SMILES: C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)C1CC3

Synonyms [en]

3-Keto-4-methylzymosterol; 3-dehydro-4-methylzymosterol; 4-methyl-5alpha-cholesta-8,24-dien-3-one; (5alpha)-4-methylcholesta-8,24-dien-3-one; 13-dimethyl-17-(2R)-6-methyl-5-methylideneheptan-2-yl-4; 24-dien-3-one

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

3-Keto-4-methylzymosterol. 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: BioCAD00000003611). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

3-Keto-4-methylzymosterol is an intermediate in the biosynthesis of steroids (KEGG:C15816). It is the 8th to last step in the synthesis of vitamin D2 and is converted from 4-methtylzymosterol-carboxylate via the enzyme sterol-4alpha-carboxylate 3-dehydrogenase (decarboxylating) (EC:1.1.1.170). It is then converted to 4-methylzymosterol via the enzyme 3-keto steroid reductase (EC:1.1.1.270).

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 7377-73-3
  • PubChem: 24906328
  • PubChem: 53477900
  • ChEBI: ChEBI:181923
  • ChEBI: ChEBI:505093
  • ChEBI: ChEBI:50593
  • HMDB: HMDB0006838
  • LipidMaps: LMST01010167
  • KEGG: C15816
  • BioCyc: CPD-4578
  • RefMet: RM0189043
  • Coconut NaturalProduct: CNP0243509.1
  • Coconut NaturalProduct: CNP0243509.2
  • Coconut NaturalProduct: CNP0243509.3
  • Coconut NaturalProduct: CNP0321294.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R07494 1.1.1.170 C15808 + C00006<=>C15816 + C00005 + C00080 + C00011
KEGG:R07495 1.1.1.270 4alpha-methylzymosterol:NADP+ 3-oxidoreductase
Rhea:RHEA:33448 1.1.1.170 4β-methylzymosterol-4α-carboxylate + NADP+ => 3-dehydro-4-methylzymosterol + CO2 + NADPH
Rhea:RHEA:33449 1.1.1.170 3-dehydro-4-methylzymosterol + CO2 + NADPH => 4β-methylzymosterol-4α-carboxylate + NADP+
Rhea:RHEA:33450 1.1.1.170 4β-methylzymosterol-4α-carboxylate + NADP+ <=> 3-dehydro-4-methylzymosterol + CO2 + NADPH
Rhea:RHEA:47161 4β-methylzymosterol-4α-carboxylate + NAD+ => 3-dehydro-4-methylzymosterol + CO2 + NADH
Rhea:RHEA:47162 3-dehydro-4-methylzymosterol + CO2 + NADH => 4β-methylzymosterol-4α-carboxylate + NAD+
Rhea:RHEA:47163 4β-methylzymosterol-4α-carboxylate + NAD+ <=> 3-dehydro-4-methylzymosterol + CO2 + NADH
BioCyc:RXN-20373 1.1.1.418 CPD-4577 + NAD --> CPD-4578 + NADH + CARBON-DIOXIDE
BioCyc:RXN66-313 1.1.1.170 CPD-4577 + NAD-P-OR-NOP --> CPD-4578 + NADH-P-OR-NOP + CARBON-DIOXIDE
BioCyc:RXN-20116 1.1.1.417 CPD-21730 + NAD-P-OR-NOP --> CPD-4578 + NADH-P-OR-NOP + CARBON-DIOXIDE
BioCyc:RXN66-314 1.1.1.270 PROTON + CPD-4578 + NADPH --> 4-METHYL-824-CHOLESTADIENOL + NADP
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Organism Source

Taxonomy Source

  1. Dendronephthya gigantea [ncbi taxid: 151771]
  2. lemnalia carvicorni [ncbi taxid: ]

Pathway Synthetic

pathway id name
PlantCyc:PLANT_PWY66-341 cholesterol biosynthesis I
PlantCyc:PLANT_PWY-6074 zymosterol biosynthesis
PathBank:SMP0120794 Mevalonic Aciduria
PathBank:SMP0120464 CHILD Syndrome
PathBank:SMP0120472 Desmosterolosis
PathBank:SMP0120512 Lysosomal Acid Lipase Deficiency (Wolman Disease)
PathBank:SMP0120573 Cholesteryl Ester Storage Disease
PathBank:SMP0121057 Bloch Pathway (Cholesterol Biosynthesis)
PathBank:SMP0000023 Steroid Biosynthesis
PathBank:SMP0000387 CHILD Syndrome
PathBank:SMP0000112 Risedronate Action Pathway
PathBank:SMP0000508 Cholesteryl Ester Storage Disease
PathBank:SMP0002438 Cholesterol Biosynthesis and Metabolism CE(12:0)
PathBank:SMP0087326 Steroid Biosynthesis
PathBank:SMP0120685 Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)
PathBank:SMP0120769 Hypercholesterolemia
PathBank:SMP0120793 Hyper-IgD Syndrome
PathBank:SMP0120515 Smith-Lemli-Opitz Syndrome (SLOS)
PathBank:SMP0120576 Wolman Disease
PathBank:SMP0000389 Smith-Lemli-Opitz Syndrome (SLOS)
View All Pathways