5-Dehydroepisterol (BioCAD00000004783)

plant natural products microbial natural products

Metabolite Card

Formula: C28H44O (396.3392)
SMILES: [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C

Synonyms [en]

5-dehydroepisterol; ergosta-5,7,24(28)-trien-3beta-ol; Campesta-7,24(28)-dien-3beta-ol; Campesta-7; Ergosta-8; 11a-dodecahydro-1H-cyclopentaaphenanthren-7-ol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

5-Dehydroepisterol. 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: BioCAD00000004783). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

5-Dehydroepisterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 5-dehydroepisterol is considered to be a sterol lipid molecule. 5-Dehydroepisterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Dehydroepisterol is an intermediate in the biosynthesis of steroids and is converted from episterol via the enzyme lathosterol oxidase (EC 1.14.21.6). It is then converted into 24-methylenecholesterol via the enzyme 7-dehydrocholesterol reductase (EC 1.3.1.21).

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 23582-83-4
  • CAS Registry Number: 84223-03-0
  • PubChem: 10894570
  • ChEBI: ChEBI:52972
  • HMDB: HMDB0006848
  • LipidMaps: LMST01030135
  • KEGG: C15780
  • Wikipedia: 5-Dehydroepisterol
  • Metlin: METLIN_63316
  • Coconut NaturalProduct: CNP0137733.2
  • Coconut NaturalProduct: CNP0137733.4
  • Coconut NaturalProduct: CNP0326998.1
  • Coconut NaturalProduct: CNP0359840.1

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R07491 1.14.19.20 episterol,ferrocytochrome b5:oxygen oxidoreductase 5,6-dehydrogenating
KEGG:R07492 1.3.1.21 C15780<=>C15781
KEGG:R07506 1.14.19.41 ergosta-5,7,24(28)-trien-3beta-ol,NADPH:oxygen oxidoreductase (22,23-dehydrogenating)
Rhea:RHEA:33464 episterol + NADPH + O2 + H+ => 5-dehydroepisterol + NADP+ + 2 H2O
Rhea:RHEA:33465 5-dehydroepisterol + NADP+ + 2 H2O => episterol + NADPH + O2 + H+
Rhea:RHEA:33466 episterol + NADPH + O2 + H+ <=> 5-dehydroepisterol + NADP+ + 2 H2O
Rhea:RHEA:33468 1.14.19.41 5-dehydroepisterol + NADPH + O2 + H+ => ergosta-5,7,22,24(28)-tetraen-3β-ol + NADP+ + 2 H2O
Rhea:RHEA:33469 1.14.19.41 ergosta-5,7,22,24(28)-tetraen-3β-ol + NADP+ + 2 H2O => 5-dehydroepisterol + NADPH + O2 + H+
Rhea:RHEA:33470 1.14.19.41 5-dehydroepisterol + NADPH + O2 + H+ <=> ergosta-5,7,22,24(28)-tetraen-3β-ol + NADP+ + 2 H2O
Rhea:RHEA:34008 7-dehydrodesmosterol + S-adenosyl-L-methionine => 5-dehydroepisterol + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:34009 5-dehydroepisterol + S-adenosyl-L-homocysteine + H+ => 7-dehydrodesmosterol + S-adenosyl-L-methionine
Rhea:RHEA:34010 7-dehydrodesmosterol + S-adenosyl-L-methionine <=> 5-dehydroepisterol + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:34012 5-dehydroepisterol + NADP+ + 2 H2O => ergosta-5,7-dien-3βbeta-ol + NADPH + O2 + H+
Rhea:RHEA:34013 ergosta-5,7-dien-3βbeta-ol + NADPH + O2 + H+ => 5-dehydroepisterol + NADP+ + 2 H2O
Rhea:RHEA:34014 5-dehydroepisterol + NADP+ + 2 H2O <=> ergosta-5,7-dien-3βbeta-ol + NADPH + O2 + H+
Rhea:RHEA:46561 1.14.19.20 episterol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ => 5-dehydroepisterol + 2 Fe(III)-[cytochrome b5] + 2 H2O
Rhea:RHEA:46562 1.14.19.20 5-dehydroepisterol + 2 Fe(III)-[cytochrome b5] + 2 H2O => episterol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+
Rhea:RHEA:46563 1.14.19.20 episterol + 2 Fe(II)-[cytochrome b5] + O2 + 2 H+ <=> 5-dehydroepisterol + 2 Fe(III)-[cytochrome b5] + 2 H2O
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Organism Source

Taxonomy Source

  1. Arabidopsis thaliana [ncbi taxid: 3702]
  2. Candida albicans [ncbi taxid: 5476]
  3. Candida utilis [ncbi taxid: ]
  4. Leptosphaeria typhae [ncbi taxid: ]
  5. Mus musculus [ncbi taxid: 10090]
  6. Phycomyces blakesleeanus [ncbi taxid: 4837]
  7. Saccharomyces carlsbergensis [ncbi taxid: ]
  8. Saccharomyces cerevisiae [ncbi taxid: 4932]
  9. Saccharomyces cerevisiae (SM36 mutant strain) [ncbi taxid: ]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-6075 ergosterol biosynthesis I
BioCyc:YEAST_ERGOSTEROL-SYN-PWY superpathway of ergosterol biosynthesis
BioCyc:YEAST_PWY-6075 ergosterol biosynthesis
BioCyc:ARA_PWY-2541 plant sterol biosynthesis
BioCyc:META_ERGOSTEROL-SYN-PWY superpathway of ergosterol biosynthesis I
BioCyc:META_PWY-2541 plant sterol biosynthesis
PlantCyc:RUBBERTREE_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:SPENNELLII_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:SPIRODELA_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:SVIRIDIS_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:MGUTTATUS_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:MOSOBAMBOO_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:MOSS_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:MUSKMELON_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:OEUROPAEA_SYLVESTRIS_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:OGLABERRIMA_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:OILPALM_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:ORUFIPOGON_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:PAPAYA_PWY-2541 phytosterol biosynthesis (plants)
PlantCyc:CROSEUS_PWY-2541 phytosterol biosynthesis (plants)
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