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CHEBI:66746 - phomacin A

ChEBI IDCHEBI:66746
ChEBI Namephomacin A
Stars
DefinitionA cytochalasin isolated from a fungus Phoma sp. that has been shown to possess potent inhibitory activity against HT-29 colonic adenocarcinoma cells.
Last Modified6 August 2014
DownloadsMolfile
FormulaC25H37NO5
Net Charge0
Average Mass431.573
Monoisotopic Mass431.26717
SMILES[H][C@]12[C@H](CC(C)C)NC(=O)[C@]13OC(=O)/C=C\[C@@H](O)[C@@H](O)[C@@H](C)C/C(C)=C/[C@@]3([H])C=C(C)[C@H]2C
InChIInChI=1S/C25H37NO5/c1-13(2)9-19-22-17(6)15(4)12-18-11-14(3)10-16(5)23(29)20(27)7-8-21(28)31-25(18,22)24(30)26-19/h7-8,11-13,16-20,22-23,27,29H,9-10H2,1-6H3,(H,26,30)/b8-7-,14-11+/t16-,17+,18-,19-,20+,22-,23-,25+/m0/s1
InChIKeyCTCWWHNYPVOMQP-WXZOGCPCSA-N
Species of MetaboliteComponentSourceComments
Phoma (ncbitaxon:37463) - PubMed (11671521)
Roles Classification
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
phomacin A (CHEBI:66746) has role antineoplastic agent (CHEBI:35610)
phomacin A (CHEBI:66746) has role fungal metabolite (CHEBI:76946)
phomacin A (CHEBI:66746) is a cytochalasin (CHEBI:23528)
phomacin A (CHEBI:66746) is a macrolide antibiotic (CHEBI:25105)
phomacin A (CHEBI:66746) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name 
(3Z,5R,6S,7S,9E,10aS,13S,13aS,14S,16aR)-5,6-dihydroxy-7,9,12,13-tetramethyl-14-(2-methylpropyl)-6,7,8,10a,13,13a,14,15-octahydro-2H-oxacyclododecino[2,3-d]isoindole-2,16(5H)-dione
Citations