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CHEBI:80033 - syringolin A

ChEBI IDCHEBI:80033
ChEBI Namesyringolin A
Stars
DefinitionA 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.
Last Modified6 March 2015
DownloadsMolfile
FormulaC24H39N5O6
Net Charge0
Average Mass493.605
Monoisotopic Mass493.29003
SMILES[H][C@]1(NC(=O)[C@@H](NC(=O)N[C@H](C(=O)O)C(C)C)C(C)C)/C=C/CCNC(=O)/C=C/[C@H](C(C)C)NC1=O
InChIInChI=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
InChIKeyRUWSLQOIGKYPEZ-YPXRAQKDSA-N
Species of MetaboliteComponentSourceComments
Pseudomonas syringae pv. syringae (ncbitaxon:1365665) - PubMed (14714872) Strain: B301D-R
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
Application:
proteasome inhibitor  A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
ChEBI Ontology
Outgoing Relation(s)
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 XrefsDatabases
C15701KEGG COMPOUND
C00029068KNApSAcK
SRGPDBeChem
Citations