CHEBI:84057 - trapoxin A

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ChEBI Name trapoxin A
ChEBI ID CHEBI:84057
Definition A homodetic cyclic tetrapeptide constructed from L-phenylalanyl (x2), D-pipecolinyl and L-2-amino-8-oxo-9,10-epoxydecanoyl residues.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C34H42N4O6
Net Charge 0
Average Mass 602.72050
Monoisotopic Mass 602.31044
InChI InChI=1S/C34H42N4O6/c39-29(30-22-44-30)18-9-3-8-16-25-31(40)36-26(20-23-12-4-1-5-13-23)32(41)37-27(21-24-14-6-2-7-15-24)34(43)38-19-11-10-17-28(38)33(42)35-25/h1-2,4-7,12-15,25-28,30H,3,8-11,16-22H2,(H,35,42)(H,36,40)(H,37,41)/t25-,26-,27-,28+,30-/m0/s1
InChIKey GXVXXETYXSPSOA-UFEOFEBPSA-N
SMILES O=C(CCCCC[C@@H]1NC(=O)[C@H]2CCCCN2C(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc2ccccc2)NC1=O)[C@@H]1CO1
Metabolite of Species Details
Helicoma ambiens (NCBI:txid314151) of strain RF-1023 See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 3.5.1.98 (histone deacetylase) inhibitor
An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98).
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing trapoxin A (CHEBI:84057) has role antineoplastic agent (CHEBI:35610)
trapoxin A (CHEBI:84057) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115)
trapoxin A (CHEBI:84057) has role fungal metabolite (CHEBI:76946)
trapoxin A (CHEBI:84057) is a epoxide (CHEBI:32955)
trapoxin A (CHEBI:84057) is a homodetic cyclic peptide (CHEBI:24613)
trapoxin A (CHEBI:84057) is a ketone (CHEBI:17087)
IUPAC Name
(3S,6S,9S,15aR)-6,9-dibenzyl-3-{6-[(2S)-oxiran-2-yl]-6-oxohexyl}octahydro-2H-pyrido[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10(3H,12H)-tetrone
Synonyms Sources
Cyclo((S)-gamma-oxo-L-alpha-aminooxiraneoctanoyl-L-phenylalanyl-L-phenylalanyl-D-2-piperidinecarbonyl) ChemIDplus
Cyclo((S)-phenylalanyl-(S)-phenylalanyl-(R)-pipecolinyl-(2S,9S)-2-amino-8-oxo-9,10-epoxydecanoyl) ChemIDplus
RF 1023A KNApSAcK
Manual Xref Database
C00017061 KNApSAcK
View more database links
Registry Numbers Types Sources
133155-89-2 CAS Registry Number ChemIDplus
8817133 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1930826 PubMed citation Europe PMC
2276972 PubMed citation Europe PMC
Last Modified
15 January 2015