CHEBI:8047 - phaseolotoxin

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ChEBI Name phaseolotoxin
ChEBI ID CHEBI:8047
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C14H32N9O8PS
Net Charge 0
Average Mass 517.500
Monoisotopic Mass 517.18322
InChI InChI=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
InChIKey JXFJDYCRCSOLAG-SKTDGYGZSA-N
SMILES [C@H](NC([C@@H](NC([C@H](CCCNP(NS(O)(=O)=O)(=O)N)N)=O)C)=O)(CCCNC(N)=N)C(O)=O
Metabolite of Species Details
Pseudomonas syringae (NCBI:txid317) See: DOI
Pseudomonas syringae (NCBI:txid317) of strain Pseudomonas syringae pv. phaseolicola NPS312 See: J. Gen. Plant Pathol., 2018, 84, 137-141
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): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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).
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
N5-[amino(sulfoamino)phosphinyl]-L-ornithyl-L-alanyl-N6-(aminoiminomethyl)-L-lysine KEGG COMPOUND
Nδ-(N'-sulphodiaminophosphinyl)-ornithyl-alanyl-homoarginine ChemIDplus
phaseolotoxin A ChemIDplus
Manual Xrefs Databases
C00001520 KNApSAcK
C08440 KEGG COMPOUND
FDB001499 FooDB
View more database links
Registry Numbers Types Sources
62249-77-8 CAS Registry Number KEGG COMPOUND
62249-77-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14687626 PubMed citation Europe PMC
21542933 PubMed citation Europe PMC
26256666 PubMed citation Europe PMC
28570637 PubMed citation Europe PMC
29132716 PubMed citation Europe PMC
496962 PubMed citation Europe PMC
IND605901583 Agricola citation Europe PMC
IND606053992 Agricola citation Europe PMC
Last Modified
29 January 2019
General Comment
2019-01-29 For revision of the structure, see Tetrahedron Lett., 1984, 25, 3931-3934. For other relevant articles, see Mitchell, R.E. (1989) Current research into chemical synthesis of phaseolotoxin. in: Graniti A., Durbin R.D., Ballio A. (eds) Phytotoxins and Plant Pathogenesis, 27, 1-6.