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CHEBI:84057 - trapoxin A

ChEBI IDCHEBI:84057
ChEBI Nametrapoxin A
Stars
DefinitionA homodetic cyclic tetrapeptide constructed from L-phenylalanyl (x2), D-pipecolinyl and L-2-amino-8-oxo-9,10-epoxydecanoyl residues.
Last Modified15 January 2015
SubmitterSteve
DownloadsMolfile
FormulaC34H42N4O6
Net Charge0
Average Mass602.732
Monoisotopic Mass602.31044
SMILES[H][C@]12CCCCN1C(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCCCCC(=O)[C@@H]1CO1)NC2=O
InChIInChI=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
InChIKeyGXVXXETYXSPSOA-UFEOFEBPSA-N
Species of MetaboliteComponentSourceComments
Helicoma ambiens (ncbitaxon:314151) - PubMed (2276972) Strain: RF-1023
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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  Source
RF 1023AKNApSAcK
Cyclo((S)-phenylalanyl-(S)-phenylalanyl-(R)-pipecolinyl-(2S,9S)-2-amino-8-oxo-9,10-epoxydecanoyl)ChemIDplus
Cyclo((S)-gamma-oxo-L-alpha-aminooxiraneoctanoyl-L-phenylalanyl-L-phenylalanyl-D-2-piperidinecarbonyl)ChemIDplus
Manual XrefsDatabases
C00017061KNApSAcK
Registry NumbersSources
Reaxys:8817133Reaxys
CAS:133155-89-2ChemIDplus
Citations