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CHEBI:8047 - phaseolotoxin

ChEBI IDCHEBI:8047
ChEBI Namephaseolotoxin
Stars
DefinitionA tripeptide resulting from the formal condensation of the carboxy group of N5-[amino(sulfoamino)phosphoryl]-L-ornithine with the N-terminal amino group of L-alanyl-L-arginine. A toxin produced by cultured Pseudomonas syringae, the causal agent of halo blight disease in bean plants.
Last Modified29 January 2019
DownloadsMolfile
FormulaC14H32N9O8PS
Net Charge0
Average Mass517.506
Monoisotopic Mass517.18322
SMILESC[C@H](NC(=O)[C@@H](N)CCCNP(N)(=O)NS(=O)(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O
InChIInChI=1S/C14H32N9O8PS/c1-8(11(24)22-10(13(26)27)5-3-6-19-14(16)17)21-12(25)9(15)4-2-7-20-32(18,28)23-33(29,30)31/h8-10H,2-7,15H2,1H3,(H,21,25)(H,22,24)(H,26,27)(H4,16,17,19)(H,29,30,31)(H4,18,20,23,28)/t8-,9-,10-,32?/m0/s1
InChIKeyJXFJDYCRCSOLAG-SKTDGYGZSA-N
Species of MetaboliteComponentSourceComments
Pseudomonas syringae (ncbitaxon:317)
- DOI (10.1016/0040-4039(84)80033-7)
- Article (J. Gen. Plant Pathol., 2018, 84, 137-141) Strain: Pseudomonas syringae pv. phaseolicola NPS312
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
EC 2.1.3.3 (ornithine carbamoyltransferase) inhibitor  Any EC 2.1.3.* (carboxy- and carbamoyltransferases) inhibitor that inhibits the action of ornithine carbamoyltransferase (EC 2.1.3.3).
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
phaseolotoxin (CHEBI:8047) has functional parent sulfamic acid (CHEBI:9330)
phaseolotoxin (CHEBI:8047) has role antineoplastic agent (CHEBI:35610)
phaseolotoxin (CHEBI:8047) has role bacterial metabolite (CHEBI:76969)
phaseolotoxin (CHEBI:8047) has role EC 2.1.3.3 (ornithine carbamoyltransferase) inhibitor (CHEBI:143003)
phaseolotoxin (CHEBI:8047) is a guanidines (CHEBI:24436)
phaseolotoxin (CHEBI:8047) is a tripeptide (CHEBI:47923)
IUPAC Name 
N5-[amino(sulfoamino)phosphoryl]-L-ornithyl-L-alanyl-L-arginine
Synonyms  Source
N5-[amino(sulfoamino)phosphinyl]-L-ornithyl-L-alanyl-N6-(aminoiminomethyl)-L-lysineKEGG COMPOUND
Nδ-(N'-sulphodiaminophosphinyl)-ornithyl-alanyl-homoarginineChemIDplus
phaseolotoxin AChemIDplus
Manual XrefsDatabases
C08440KEGG COMPOUND
C00001520KNApSAcK
FDB001499FooDB
Registry NumbersSources
CAS:62249-77-8KEGG COMPOUND
CAS:62249-77-8ChemIDplus
Citations