CHEBI:84711 - staphyloferrin A

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ChEBI Name staphyloferrin A
ChEBI ID CHEBI:84711
Definition A D-ornithine derivative obtained by formal condensation of the terminal carboxy groups of two citric acid units with the two amino groups of D-ornithine.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C17H24N2O14
Net Charge 0
Average Mass 480.37750
Monoisotopic Mass 480.12275
InChI InChI=1S/C17H24N2O14/c20-9(4-16(32,14(28)29)6-11(22)23)18-3-1-2-8(13(26)27)19-10(21)5-17(33,15(30)31)7-12(24)25/h8,32-33H,1-7H2,(H,18,20)(H,19,21)(H,22,23)(H,24,25)(H,26,27)(H,28,29)(H,30,31)/t8-,16?,17?/m1/s1
InChIKey VJSIXUQLTJCRCS-PJPOUAMNSA-N
SMILES OC(=O)CC(O)(CC(=O)NCCC[C@@H](NC(=O)CC(O)(CC(O)=O)C(O)=O)C(O)=O)C(O)=O
Metabolite of Species Details
Staphylococcus hyicus (NCBI:txid1284) of strain DSM 20459 See: PubMed
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.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing staphyloferrin A (CHEBI:84711) has functional parent citric acid (CHEBI:30769)
staphyloferrin A (CHEBI:84711) has role bacterial metabolite (CHEBI:76969)
staphyloferrin A (CHEBI:84711) has role siderophore (CHEBI:26672)
staphyloferrin A (CHEBI:84711) is a D-ornithine derivative (CHEBI:84714)
staphyloferrin A (CHEBI:84711) is a pentacarboxylic acid (CHEBI:35743)
staphyloferrin A (CHEBI:84711) is a tertiary alcohol (CHEBI:26878)
staphyloferrin A (CHEBI:84711) is a tricarboxylic acid amide (CHEBI:50665)
staphyloferrin A (CHEBI:84711) is conjugate acid of staphyloferrin A(5−) (CHEBI:142973)
Incoming N5-[(S)-citryl]-D-ornithine(2−) (CHEBI:142972) has functional parent staphyloferrin A (CHEBI:84711)
staphyloferrin A(5−) (CHEBI:142973) is conjugate base of staphyloferrin A (CHEBI:84711)
IUPAC Name
2-[2-({(1R)-1-carboxy-4-[(3,4-dicarboxy-3-hydroxybutanoyl)amino]butyl}amino)-2-oxoethyl]-2-hydroxysuccinic acid
Synonym Source
N2,N5-di-(1-oxo-3-hydroxy-3,4-dicarboxybutyl)-D-ornithine ChEBI
Manual Xref Database
CPD-12589 MetaCyc
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Registry Numbers Types Sources
127902-98-1 CAS Registry Number ChemIDplus
26649296 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
2139423 PubMed citation Europe PMC
23575952 PubMed citation Europe PMC
2379505 PubMed citation Europe PMC
24500249 PubMed citation Europe PMC
25050909 PubMed citation Europe PMC
Last Modified
05 February 2015