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CHEBI:230243 - verrucarin A

ChEBI IDCHEBI:230243
ChEBI Nameverrucarin A
Stars
DefinitionA trichothecene antibiotic which incorporates a triester macrocyclic structure and an exocyclic methylene epoxide group.
Secondary ChEBI IDCHEBI:9968
Last Modified2 December 2019
DownloadsMolfile
FormulaC27H34O9
Net Charge0
Average Mass502.560
Monoisotopic Mass502.22028
SMILES[H][C@@]12C=C(C)CC[C@@]13COC(=O)[C@@H](O)[C@H](C)CCOC(=O)/C=C/C=C\C(=O)O[C@@H]1C[C@@]([H])(O2)[C@@]2(CO2)[C@]13C
InChIInChI=1S/C27H34O9/c1-16-8-10-26-14-33-24(31)23(30)17(2)9-11-32-21(28)6-4-5-7-22(29)36-18-13-20(35-19(26)12-16)27(15-34-27)25(18,26)3/h4-7,12,17-20,23,30H,8-11,13-15H2,1-3H3/b6-4+,7-5-/t17-,18-,19-,20-,23+,25-,26-,27+/m1/s1
InChIKeyNLUGUZJQJYVUHS-IDXDZYHTSA-N
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
mycotoxin  Poisonous substance produced by fungi.
ChEBI Ontology
Outgoing Relation(s)
verrucarin A (CHEBI:230243) is a epoxide (CHEBI:32955)
verrucarin A (CHEBI:230243) is a macrolide antibiotic (CHEBI:25105)
verrucarin A (CHEBI:230243) is a macrotriolide (CHEBI:145559)
verrucarin A (CHEBI:230243) is a organic heterotetracyclic compound (CHEBI:38163)
verrucarin A (CHEBI:230243) is a trichothecene (CHEBI:55517)
IUPAC Name 
(4S,5R,10E,12Z,16R,16aS,17S,18R,19aR,23aR)-4-hydroxy-5,16a,21-trimethyl-4,5,6,7,16,16a,22,23-octahydro-3H,18H,19aH-spiro[16,18-methano[1,6,12]trioxacyclooctadecino[3,4-d]chromene-17,2'-oxirane]-3,9,14-trione
Synonyms  Source
Verrucarin AKEGG COMPOUND
Muconomycin AKEGG COMPOUND
Manual XrefsDatabases
C09746KEGG COMPOUND
C00003200KNApSAcK
Registry NumbersSources
Beilstein:1612598Beilstein
CAS:3148-09-2KEGG COMPOUND
CAS:3148-09-2ChemIDplus