24-Methylenelophenol (BioCAD00000003231)

plant natural products

Metabolite Card

Formula: C29H48O (412.3705)
SMILES: [H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@H](C)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C

Synonyms [en]

24-Methylenelophenol; 24-Methylene lophenol; 24-methylidenelophenol; 4alpha-Methyl-24-methylene-5alpha-cholest-7-en-3beta-ol; 4-alpha-Methyl-5-alpha-ergosta-7,24-dien-3-beta-ol; 4alpha-Methylepisterol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

24-Methylenelophenol. 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: BioCAD00000003231). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

24-Methylenelophenol is involved in the biosynthesis of steroids. 24-Methylenelophenol is converted from 4alpha-methylfecosterol by cholestenol delta-isomerase (EC: 5.3.3.5). 24-Methylenelophenol is converted into 24-ethylidenelophenol by 24-methylenesterol C-methyltransferase (EC 2.1.1.143). 24-Methylenelophenol can also be converted into episterol.

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 1176-52-9
  • PubChem: 5283640
  • ChEBI: ChEBI:29107
  • HMDB: HMDB0006846
  • HMDB: HMDB06846
  • LipidMaps: LMST01030100
  • KEGG: C11522
  • BioCyc: CPD-4101
  • Metlin: METLIN_63312
  • Coconut NaturalProduct: CNP0179208.1
  • Coconut NaturalProduct: CNP0179208.5

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R05776 2.1.1.143 S-adenosyl-L-methionine:24-methylenelophenol C-methyltransferase
KEGG:R07484 5.3.3.5 C15776<=>C11522
KEGG:R12372 1.14.18.11 24-methylenelophenol,ferrocytochrome-b5:oxygen oxidoreductase
KEGG:R12378 1.14.18.11 24-methylenelophenol,ferrocytochrome-b5:oxygen oxidoreductase (C-4alpha-methyl-hydroxylating)
Rhea:RHEA:21045 2.1.1.143 24-methylidenelophenol + S-adenosyl-L-methionine => (Z)-24-ethylidenelophenol + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:21046 2.1.1.143 (Z)-24-ethylidenelophenol + S-adenosyl-L-homocysteine + H+ => 24-methylidenelophenol + S-adenosyl-L-methionine
Rhea:RHEA:21047 2.1.1.143 24-methylidenelophenol + S-adenosyl-L-methionine <=> (Z)-24-ethylidenelophenol + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:58869 1.14.18.11 24-methylidenelophenol + 6 Fe(II)-[cytochrome b5] + 3 O2 + 5 H+ => 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + 6 Fe(III)-[cytochrome b5] + 4 H2O
Rhea:RHEA:58870 1.14.18.11 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + 6 Fe(III)-[cytochrome b5] + 4 H2O => 24-methylidenelophenol + 6 Fe(II)-[cytochrome b5] + 3 O2 + 5 H+
Rhea:RHEA:58871 1.14.18.11 24-methylidenelophenol + 6 Fe(II)-[cytochrome b5] + 3 O2 + 5 H+ <=> 4α-carboxy-ergosta-7,24(241)-dien-3β-ol + 6 Fe(III)-[cytochrome b5] + 4 H2O
Rhea:RHEA:58873 24-methylidenelophenol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ => 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + 2 Fe(III)-[cytochrome b5] + H2O
Rhea:RHEA:58874 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + 2 Fe(III)-[cytochrome b5] + H2O => 24-methylidenelophenol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+
Rhea:RHEA:58875 24-methylidenelophenol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ <=> 4α-hydroxymethyl-ergosta-7,24(241)-dien-3β-ol + 2 Fe(III)-[cytochrome b5] + H2O
BioCyc:RXN-11930 CPD-4101 + OXYGEN-MOLECULE + 2 FERROCYTOCHROME-B5 + 2 PROTON --> CPD-12907 + 2 FERRICYTOCHROME-B5 + WATER
BioCyc:RXN-19724 1.14.18.11 CPD-4101 + 3 OXYGEN-MOLECULE + 6 FERROCYTOCHROME-B5 + 5 PROTON --> CPD-12909 + 6 FERRICYTOCHROME-B5 + 4 WATER
BioCyc:RXN-4161 5.3.3.5 CPD-4101<=>CPD-4081
BioCyc:RXN-22199 2.1.1.- S-ADENOSYLMETHIONINE + CPD-4101 --> ADENOSYL-HOMO-CYS + CPD-24186 + PROTON
BioCyc:2.1.1.143-RXN 2.1.1.143 S-ADENOSYLMETHIONINE + CPD-4101 --> PROTON + CPD-4124 + ADENOSYL-HOMO-CYS
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Organism Source

Taxonomy Source

  1. Arabidopsis thaliana [ncbi taxid: 3702]
  2. Capparis spinosa [ncbi taxid: 65558]
  3. Cassia obtusifolia [ncbi taxid: ]
  4. Coleostephus myconis [ncbi taxid: 99042]
  5. Corylus avellana [ncbi taxid: 13451]
  6. Corylus maxima [ncbi taxid: 126985]
  7. Crotone hieronymi [ncbi taxid: ]
  8. Dahlia pinnata [ncbi taxid: 101596]
  9. Gynostemma pentaphyllum [ncbi taxid: 182084]
  10. Mus musculus [ncbi taxid: 10090]
  11. Nicotiana benthamiana [ncbi taxid: 4100]
  12. Oenothera biennis [ncbi taxid: 3942]
  13. Pertusaria wulfenii [ncbi taxid: ]
  14. Physalis alkekengi var. franchetii [ncbi taxid: ]
  15. Pisum sativum [ncbi taxid: ]
  16. Saccharum officinarum [ncbi taxid: 4547]
  17. Saccharum officinarum L. [ncbi taxid: ]
  18. Saccharum sinensis [ncbi taxid: ]
  19. Sideritis discolor [ncbi taxid: 403019]
  20. Solanum tuberosum [ncbi taxid: 4113]
  21. Solanum tuberosum L. [ncbi taxid: ]
  22. Synotis alata [ncbi taxid: 308345]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-2541 plant sterol biosynthesis
Plant Reactome:R-HVU-1119370 Sterol biosynthesis
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-TAE-2744344 Secondary metabolism
Plant Reactome:R-TAE-1119370 Sterol biosynthesis
Plant Reactome:R-MES-2744345 Metabolism and regulation
Plant Reactome:R-TDI-2744345 Metabolism and regulation
Plant Reactome:R-DRO-2744345 Metabolism and regulation
Plant Reactome:R-DRO-1119370 Sterol biosynthesis
Plant Reactome:R-PTI-2744345 Metabolism and regulation
Plant Reactome:R-PTI-1119370 Sterol biosynthesis
Plant Reactome:R-GMA-2744345 Metabolism and regulation
Plant Reactome:R-GMA-2744344 Secondary metabolism
Plant Reactome:R-PDA-2744345 Metabolism and regulation
Plant Reactome:R-PVU-2744345 Metabolism and regulation
Plant Reactome:R-BRA-1119370 Sterol biosynthesis
Plant Reactome:R-OPU-1119370 Sterol biosynthesis
Plant Reactome:R-DCA-1119370 Sterol biosynthesis
Plant Reactome:R-CSI-2744345 Metabolism and regulation
Plant Reactome:R-CSI-1119370 Sterol biosynthesis
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