CHEBI:74252 - rhizobactin 1021

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ChEBI Name rhizobactin 1021
ChEBI ID CHEBI:74252
Definition A hydoxy monocarboxylic acid that is citric acid in which the two carboxy groups attached to methylene groups have each been converted to the carboxamide arising by formal condensation with the primary amino group of N-hydroxypropane-1,3-diamine and in which the nitrogen of one of the hydroxylamino groups has been acetylated while the other has been acylated with a (2E)-dec-2-enoyl group. Rhizobactin 1021 is a siderophore obtained fromj the nitrogen-fixing alfalfa symbiont Rhizobium meliloti 1021.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H42N4O9
Net Charge 0
Average Mass 530.61170
Monoisotopic Mass 530.29518
InChI InChI=1S/C24H42N4O9/c1-3-4-5-6-7-8-9-12-22(32)28(37)16-11-14-26-21(31)18-24(35,23(33)34)17-20(30)25-13-10-15-27(36)19(2)29/h9,12,35-37H,3-8,10-11,13-18H2,1-2H3,(H,25,30)(H,26,31)(H,33,34)/b12-9+
InChIKey WRSKPFYPBJAAEG-FMIVXFBMSA-N
SMILES CCCCCCC\C=C\C(=O)N(O)CCCNC(=O)CC(O)(CC(=O)NCCCN(O)C(C)=O)C(O)=O
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.
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ChEBI Ontology
Outgoing rhizobactin 1021 (CHEBI:74252) has functional parent citric acid (CHEBI:30769)
rhizobactin 1021 (CHEBI:74252) has role siderophore (CHEBI:26672)
rhizobactin 1021 (CHEBI:74252) is a hydroxamic acid (CHEBI:24650)
rhizobactin 1021 (CHEBI:74252) is a hydroxy monocarboxylic acid (CHEBI:35868)
rhizobactin 1021 (CHEBI:74252) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
4-({3-[acetyl(hydroxy)amino]propyl}amino)-2-[2-({3-[(2E)-dec-2-enoyl(hydroxy)amino]propyl}amino)-2-oxoethyl]-2-hydroxy-4-oxobutanoic acid
Synonym Source
rhizobactin-1021 ChEBI
Manual Xref Database
CPD-1021 MetaCyc
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Registry Number Type Source
6357985 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11274118 PubMed citation Europe PMC
15126460 PubMed citation Europe PMC
15899411 PubMed citation Europe PMC
15990296 PubMed citation Europe PMC
20210991 PubMed citation Europe PMC
IND22062799 Agricola citation Europe PMC
Last Modified
21 June 2013
General Comment
2013-06-21 For isolation and structure, see Persmark, M. et al., J. Am. Chem. Soc., 1993, 115(10), 3950-3956.