rhizobactin 1021 (CHEBI:74252)

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CHEBI:74252 - rhizobactin 1021

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ChEBI ID	CHEBI:74252
ChEBI Name	rhizobactin 1021
Stars
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.
Last Modified	21 June 2013
Submitter	Gareth Owen
Downloads	Molfile

Formula	C24H42N4O9
Net Charge	0
Average Mass	530.619
Monoisotopic Mass	530.29518
SMILES	CCCCCCC/C=C/C(=O)N(O)CCCNC(=O)CC(O)(CC(=O)NCCCN(O)C(C)=O)C(=O)O
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

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 Role:	siderophore Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.

ChEBI Ontology

Outgoing Relation(s)
	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 Xrefs	Databases
CPD-1021	MetaCyc

Registry Numbers	Sources
Reaxys:6357985	Reaxys

Citations