CHEBI:65858 - ergosterol peroxide

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ChEBI Name ergosterol peroxide
ChEBI ID CHEBI:65858
Definition An ergostanoid that is ergosta-6,22-dien-3-ol with a peroxy group between positions 5 and 8 (the 3β,5α,8α,22E stereoisomer). Isolated from Ganoderma lucidum and Cordyceps sinensis, it exhibits antimycobacterial, trypanocidal and antineoplastic activities.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C28H44O3
Net Charge 0
Average Mass 428.64720
Monoisotopic Mass 428.329
InChI InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,24+,25+,26+,27+,28-/m0/s1
InChIKey VXOZCESVZIRHCJ-KGHQQZOUSA-N
SMILES [H][C@@]1(CC[C@]2([H])[C@]1(C)CC[C@]1([H])[C@@]3(C)CC[C@H](O)C[C@@]33OO[C@@]21C=C3)[C@H](C)\C=C\[C@H](C)C(C)C
Metabolite of Species Details
Phomopsis archeri (IF:113952) Found in mycelium (BTO:0001436). Endophytic fungus isolated from cortex stem of Vanilla albidia and combined Mycelial extract See: PubMed
Radermachera boniana (IPNI:110489-1) Found in twig (BTO:0001411). Ethylacetate extract of dried and ground mixture of twigs and leaves See: PubMed
Radermachera boniana (IPNI:110489-1) Found in leaf (BTO:0000713). Ethylacetate extract of dried and ground mixture of twigs and leaves See: PubMed
Sarcodon aspratus (NCBI:155012) See: PubMed
Taiwanofungus camphoratus (NCBI:196114) Found in fruit body (BTO:0000487). Parasitic to the inner heartwood wall of old hollow trunks of Cinnamomum kanehirai, EtOH extract See: PubMed
Breynia fruticosa (NCBI:296042) Found in root (BTO:0001188). 90% Methanolic extract of air-dried, crushed roots See: PubMed
Pisonia aculeata (NCBI:363212) Found in stem (BTO:0001300). Cold methanolic extract of dried stems and roots See: PubMed
Pisonia aculeata (NCBI:363212) Found in root (BTO:0001188). Cold methanolic extract of dried stems and roots See: PubMed
Penicillium commune (NCBI:36653) Found in mycelium (BTO:0001436). Methanolic extract of mycelia and ethyl acetate extract of culture broth of strain QSD 17 See: PubMed
Xylaria (NCBI:37991) Endolichenic fungi isolated from Leptogium saturninum and EtOAc extract of fermented rice substrate See: PubMed
Chaetomium globosum (NCBI:38033) See: PubMed
Aspergillus ochraceus (NCBI:40380) Found in mycelium (BTO:0001436). MeOH(mycelia) & EtOAc(broth) extract of an endophytic fungus isolated from Sargassum kjellmanianum of strain EN 31 See: PubMed
Daedaleopsis confragosa (NCBI:40433) See: PubMed
Daedalea quercina (NCBI:40437) See: PubMed
Ganoderma lucidum (NCBI:5315) Found in fruit body (BTO:0000487). See: PubMed
Chaetomium longirostre (NCBI:669026) See: PubMed
Chaetomium longirostre (NCBI:669026) Ethyl acetate extract of dried fungal biomass See: PubMed
Cordyceps sinensis (NCBI:72228) Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed
Cordyceps sinensis (NCBI:72228) Found in mycelium (BTO:0001436). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimycobacterial drug
A drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy.
trypanocidal drug
A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
Application(s): antimycobacterial drug
A drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy.
trypanocidal drug
A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ergosterol peroxide (CHEBI:65858) has functional parent ergosterol (CHEBI:16933)
ergosterol peroxide (CHEBI:65858) has role antimycobacterial drug (CHEBI:64912)
ergosterol peroxide (CHEBI:65858) has role antineoplastic agent (CHEBI:35610)
ergosterol peroxide (CHEBI:65858) has role metabolite (CHEBI:25212)
ergosterol peroxide (CHEBI:65858) has role trypanocidal drug (CHEBI:36335)
ergosterol peroxide (CHEBI:65858) is a 3β-sterol (CHEBI:35348)
ergosterol peroxide (CHEBI:65858) is a ergostanoid (CHEBI:50403)
ergosterol peroxide (CHEBI:65858) is a organic peroxide (CHEBI:25702)
ergosterol peroxide (CHEBI:65858) is a phytosterols (CHEBI:26125)
IUPAC Name
(3S,5S,8S,9R,10R,13R,14R,17R)-17-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol
Synonyms Sources
(22E,24R)-5α,8α-epidioxyergosta-6,22-dien-3β-ol ChEBI
(24R)-5α,8α-epidioxy-24-methylcholesta-6,22-dien-3β-ol ChEBI
(3β,5α,8α,22E)-5,8-epidioxyergosta-6,22-dien-3-ol ChemIDplus
5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol ChEBI
ergosterol 5α,8α-epidioxide ChemIDplus
ergosterol endoperoxide ChemIDplus
ergosterol-5,8-peroxide ChemIDplus
peroxyergosterol ChemIDplus
Database Links Databases
4508532 Chemspider accession
Ergosterol_peroxide Wikipedia
View more database links
Registry Numbers Types Sources
2061-64-5 CAS Registry Number ChemIDplus
96852 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10423860 PubMed citation Europe PMC
11014261 PubMed citation Europe PMC
15665489 PubMed citation Europe PMC
21341709 PubMed citation Europe PMC
21428374 PubMed citation Europe PMC
21469696 PubMed citation Europe PMC
22083593 PubMed citation Europe PMC
9635497 PubMed citation Europe PMC
Last Modified
22 January 2013