CHEBI:230243 - verrucarin A

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ChEBI Name verrucarin A
ChEBI ID CHEBI:230243
Definition A trichothecene antibiotic which incorporates a triester macrocyclic structure and an exocyclic methylene epoxide group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:9968
Supplier Information
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Formula C27H34O9
Net Charge 0
Average Mass 502.55350
Monoisotopic Mass 502.22028
InChI InChI=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
InChIKey NLUGUZJQJYVUHS-IDXDZYHTSA-N
SMILES [H][C@]12C[C@H]3OC(=O)\C=C/C=C/C(=O)OCC[C@@H](C)[C@H](O)C(=O)OC[C@@]4(CCC(C)=C[C@@]4([H])O1)[C@]3(C)[C@]21CO1
Roles Classification
Biological Role(s): mycotoxin
Poisonous substance produced by fungi.
(via trichothecene )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via macrolide antibiotic )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
Muconomycin A KEGG COMPOUND
Verrucarin A KEGG COMPOUND
Manual Xrefs Databases
C00003200 KNApSAcK
C09746 KEGG COMPOUND
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Registry Numbers Types Sources
1612598 Beilstein Registry Number Beilstein
3148-09-2 CAS Registry Number KEGG COMPOUND
3148-09-2 CAS Registry Number ChemIDplus
Last Modified
02 December 2019