CHEBI:16933 - ergosterol

ChEBI IDCHEBI:16933
ChEBI Nameergosterol
Stars
DefinitionA phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3β-hydroxy group.
Secondary ChEBI IDsCHEBI:4825, CHEBI:14214, CHEBI:23942, CHEBI:42264
Last Modified5 September 2024
DownloadsMolfile
FormulaC28H44O
Net Charge0
Average Mass396.659
Monoisotopic Mass396.33922
SMILES[H][C@@]12CC[C@]([H])([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]1(C)CC[C@@]1([H])C2=CC=C2C[C@@H](O)CC[C@@]21C
InChIInChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
InChIKeyDNVPQKQSNYMLRS-APGDWVJJSA-N
Species of MetaboliteComponentSourceComments
Xylaria (ncbitaxon:37991) - PubMed (21428374) Endolichenic fungi isolated from Leptogium saturninum and EtOAc extract of fermented rice substrate
Microdiplodia (ncbitaxon:371130) - PubMed (21244021) EtOAc extract of an endophytic fungi isolated from Lycium intricatum Strain: 9907
Phomopsis archeri (fungorum:113952) mycelium (BTO:0001436) PubMed (21341709) Endophytic fungus isolated from cortex stem of Vanilla albidia and combined Mycelial extract
Chaetomium arcuatum (ncbitaxon:911086) - CiteXplore (c6148)
Chaetomium globosum (ncbitaxon:38033) - PubMed (12357398)
Chaetomium brasiliense (ncbitaxon:155871) - PubMed (19663417)
Chaetomium longirostre (ncbitaxon:669026)
- PubMed (22004007)
- PubMed (22004007) Ethyl acetate extract of dried fungal biomass
Cordyceps sinensis (ncbitaxon:72228) mycelium (BTO:0001436) PubMed (21848266) Ethanolic extract of dried mycelia
Hypocrella (ncbitaxon:42305) mycelium (BTO:0001436) PubMed (21995505) Fungus was isolated from scale insect Strain: BCC 14524
Aspergillus ochraceus (ncbitaxon:40380) mycelium (BTO:0001436) PubMed (21043476) MeOH(mycelia) & EtOAc(broth) extract of an endophytic fungus isolated from Sargassum kjellmanianum Strain: EN 31
Saccharomyces cerevisiae (ncbitaxon:4932) - PubMed (24678285) Source: yeast.sf.net
Roles Classification
Biological Roles:
Saccharomyces cerevisiae metabolite  Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
ChEBI Ontology
Outgoing Relation(s)
ergosterol (CHEBI:16933) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
ergosterol (CHEBI:16933) has role fungal metabolite (CHEBI:76946)
ergosterol (CHEBI:16933) is a 3β-hydroxy-Δ5-steroid (CHEBI:1722)
ergosterol (CHEBI:16933) is a 3β-sterol (CHEBI:35348)
ergosterol (CHEBI:16933) is a ergostanoid (CHEBI:50403)
ergosterol (CHEBI:16933) is a phytosterols (CHEBI:26125)
Incoming Relation(s)
1-(ergostan-3β-yl)-L-aspartate (CHEBI:195261) has functional parent ergosterol (CHEBI:16933)
ergosterol peroxide (CHEBI:65858) has functional parent ergosterol (CHEBI:16933)
ergosteryl 3-β-D-glucoside (CHEBI:52973) has functional parent ergosterol (CHEBI:16933)
ergosteryl ester (CHEBI:52320) has functional parent ergosterol (CHEBI:16933)
xuezhikang (CHEBI:231891) has part ergosterol (CHEBI:16933)
(22E,24R)-5alpha,6alpha-epoxy3beta,7alpha,14beta-trihydroxy-ergosta-8,22,dien-15-one (CHEBI:231322) is a ergosterol (CHEBI:16933)
(22E,24R)-6alpha-methoxy-7alpha,15beta-dihydroxyergosta-4,8(14),22-triene-3-one (CHEBI:231321) is a ergosterol (CHEBI:16933)
IUPAC Name 
(22E)-ergosta-5,7,22-trien-3β-ol
Synonyms  Source
ErgosterolKEGG COMPOUND
Provitamin D2KEGG COMPOUND
(22E,24S)-24-methylcholesta-5,7,22-trien-3β-olJCBN
ERGOSTEROLPDBeChem
UniProt Name  Source
ergosterolUniProt
Manual XrefsDatabases
C01694KEGG COMPOUND
ERGPDBeChem
LMST01030093LIPID MAPS
DB04038DrugBank
C00003652KNApSAcK
C00023755KNApSAcK
Registry NumbersSources
Beilstein:2338604Beilstein
Reaxys:2338604Reaxys
CAS:57-87-4KEGG COMPOUND
CAS:57-87-4ChemIDplus
CAS:57-87-4NIST Chemistry WebBook