CHEBI:84585 - vibrioferrin

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ChEBI Name vibrioferrin
ChEBI ID CHEBI:84585
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C16H22N2O12
Net Charge 0
Average Mass 434.35210
Monoisotopic Mass 434.11727
InChI InChI=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
InChIKey IGQXNKDXMPSELX-BIAKFKOBSA-N
SMILES C[C@H](N1C(=O)CCC1(O)C(O)=O)C(=O)NCCOC(=O)C[C@](O)(CC(O)=O)C(O)=O
Metabolite of Species Details
Vibrio alginolyticus (NCBI:txid663) See: PubMed
Vibrio parahaemolyticus (NCBI:txid670) of strain AQ 3354 See: DOI
Roles Classification
Chemical Role(s): siderophore
Any of low-molecular-mass iron(3)-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 (Bronsted base).
(via oxoacid )
Biological Role(s): siderophore
Any of low-molecular-mass iron(3)-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.
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ChEBI Ontology
Outgoing 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 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 Numbers Types Sources
157568-17-7 CAS Registry Number ChemIDplus
8368063 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10553685 PubMed citation Europe PMC
14617658 PubMed citation Europe PMC
17116982 PubMed citation Europe PMC
19821595 PubMed citation Europe PMC
22092766 PubMed citation Europe PMC
22146715 PubMed citation Europe PMC
23772063 PubMed citation Europe PMC
7961600 PubMed citation Europe PMC
Last Modified
04 December 2018