CHEBI:80033 - syringolin A

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ChEBI Name syringolin A
ChEBI ID CHEBI:80033
Definition A syrbactin that has a (3E,9E)-2,7-dioxo-1,6-diazacyclododeca-3,9-diene skeleton that is substituted by an isopropyl group at position 5 and by a [(2S)-2-({[(1S)-1-carboxy-2-methylpropyl]carbamoyl}amino)-3-methylbutanoyl]nitrilo group at the 8-pro-S position. It is produced by the pathogenic bacterium Pseudomonas syringae pv. syringae.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H39N5O6
Net Charge 0
Average Mass 493.59640
Monoisotopic Mass 493.29003
InChI InChI=1S/C24H39N5O6/c1-13(2)16-10-11-18(30)25-12-8-7-9-17(21(31)26-16)27-22(32)19(14(3)4)28-24(35)29-20(15(5)6)23(33)34/h7,9-11,13-17,19-20H,8,12H2,1-6H3,(H,25,30)(H,26,31)(H,27,32)(H,33,34)(H2,28,29,35)/b9-7+,11-10+/t16-,17+,19+,20+/m1/s1
InChIKey RUWSLQOIGKYPEZ-YPXRAQKDSA-N
SMILES CC(C)[C@H](NC(=O)N[C@@H](C(C)C)C(=O)N[C@H]1\C=C\CCNC(=O)\C=C\[C@@H](NC1=O)C(C)C)C(O)=O
Metabolite of Species Details
Pseudomonas syringae pv. syringae (NCBI:txid1365665) of strain B301D-R See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via syrbactin )
Application(s): proteasome inhibitor
A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
(via syrbactin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing syringolin A (CHEBI:80033) has role bacterial metabolite (CHEBI:76969)
syringolin A (CHEBI:80033) is a homodetic cyclic peptide (CHEBI:24613)
syringolin A (CHEBI:80033) is a monocarboxylic acid (CHEBI:25384)
syringolin A (CHEBI:80033) is a syrbactin (CHEBI:82671)
syringolin A (CHEBI:80033) is a ureas (CHEBI:47857)
IUPAC Name
(2S)-2-({[(2S)-1-{[(3E,5S,8S,9E)-5-isopropyl-2,7-dioxo-1,6-diazacyclododeca-3,9-dien-8-yl]amino}-3-methyl-1-oxobutan-2-yl]carbamoyl}amino)-3-methylbutanoic acid
Manual Xrefs Databases
C00029068 KNApSAcK
C15701 KEGG COMPOUND
SRG PDBeChem
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Citations Waiting for Citations Types Sources
17109642 PubMed citation Europe PMC
18401409 PubMed citation Europe PMC
19746508 PubMed citation Europe PMC
19863801 PubMed citation Europe PMC
19968303 PubMed citation Europe PMC
20426399 PubMed citation Europe PMC
20597471 PubMed citation Europe PMC
20831408 PubMed citation Europe PMC
21045122 PubMed citation Europe PMC
24668894 PubMed citation Europe PMC
24727275 PubMed citation Europe PMC
Last Modified
06 March 2015