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CHEBI:84585 - vibrioferrin

ChEBI IDCHEBI:84585
ChEBI Namevibrioferrin
Stars
DefinitionA tricarboxylic acid that is citric acid in which the pro-R carboxy group has been esterified with the primary hydroxy group of 2-hydroxy-1-{(2S)-1-[(2-hydroxyethyl)amino]-1-oxopropan-2-yl}-5-oxoproline. It is a siderophore isolated from bacteria closely associated or symbiotic with toxic, bloom-forming dinoflagellates.
Last Modified4 December 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC16H22N2O12
Net Charge0
Average Mass434.354
Monoisotopic Mass434.11727
SMILESC[C@@H](C(=O)NCCOC(=O)C[C@](O)(CC(=O)O)C(=O)O)N1C(=O)CCC1(O)C(=O)O
InChIInChI=1S/C16H22N2O12/c1-8(18-9(19)2-3-16(18,29)14(26)27)12(23)17-4-5-30-11(22)7-15(28,13(24)25)6-10(20)21/h8,28-29H,2-7H2,1H3,(H,17,23)(H,20,21)(H,24,25)(H,26,27)/t8-,15+,16?/m0/s1
InChIKeyIGQXNKDXMPSELX-BIAKFKOBSA-N
Species of MetaboliteComponentSourceComments
Vibrio alginolyticus (ncbitaxon:663) - PubMed (22146715)
Vibrio parahaemolyticus (ncbitaxon:670) - DOI (DOI: 10.1111/j.1574-6968.1992.tb05311.x) Strain: AQ 3354
Roles Classification
Chemical Roles:
siderophore  Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
siderophore  Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
ChEBI Ontology
Outgoing Relation(s)
vibrioferrin (CHEBI:84585) has functional parent citric acid (CHEBI:30769)
vibrioferrin (CHEBI:84585) has role marine metabolite (CHEBI:76507)
vibrioferrin (CHEBI:84585) has role siderophore (CHEBI:26672)
vibrioferrin (CHEBI:84585) is a N-acyl hemiaminal (CHEBI:142734)
vibrioferrin (CHEBI:84585) is a carboxylic ester (CHEBI:33308)
vibrioferrin (CHEBI:84585) is a pyrrolidin-2-ones (CHEBI:74223)
vibrioferrin (CHEBI:84585) is a tertiary alcohol (CHEBI:26878)
vibrioferrin (CHEBI:84585) is a tricarboxylic acid (CHEBI:27093)
vibrioferrin (CHEBI:84585) is conjugate acid of vibrioferrin(3−) (CHEBI:84630)
Incoming Relation(s)
vibrioferrin(3−) (CHEBI:84630) is conjugate base of vibrioferrin (CHEBI:84585)
IUPAC Name 
(2R)-2-[2-(2-{[(2S)-2-(2-carboxy-2-hydroxy-5-oxopyrrolidin-1-yl)propanoyl]amino}ethoxy)-2-oxoethyl]-2-hydroxysuccinic acid
Registry NumbersSources
Reaxys:8368063Reaxys
CAS:157568-17-7ChemIDplus
Citations