CHEBI:25520 - nicotianamine

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ChEBI Name nicotianamine
ChEBI ID CHEBI:25520
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C12H21N3O6
Net Charge 0
Average Mass 303.31160
Monoisotopic Mass 303.14304
InChI InChI=1S/C12H21N3O6/c13-7(10(16)17)1-4-14-8(11(18)19)2-5-15-6-3-9(15)12(20)21/h7-9,14H,1-6,13H2,(H,16,17)(H,18,19)(H,20,21)
InChIKey KRGPXXHMOXVMMM-UHFFFAOYSA-N
SMILES NC(CCNC(CCN1CCC1C(O)=O)C(O)=O)C(O)=O
Roles Classification
Chemical Role(s): phytosiderophore
Any of low-molecular-mass iron(3)-chelating compounds produced by plants for the purpose of the transport and sequestration of iron.
(via mugineic acids )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): phytosiderophore
Any of low-molecular-mass iron(3)-chelating compounds produced by plants for the purpose of the transport and sequestration of iron.
(via mugineic acids )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nicotianamine (CHEBI:25520) is a mugineic acids (CHEBI:25427)
Incoming (R,R,R)-nicotianamine (CHEBI:38113) is a nicotianamine (CHEBI:25520)
(R,S,S)-nicotianamine (CHEBI:38114) is a nicotianamine (CHEBI:25520)
(S,R,R)-nicotianamine (CHEBI:38115) is a nicotianamine (CHEBI:25520)
(S,S,S)-nicotianamine (CHEBI:17721) is a nicotianamine (CHEBI:25520)
IUPAC Name
1-{3-[(3-amino-3-carboxypropyl)amino]-3-carboxypropyl}azetidine-2-carboxylic acid
Synonym Source
N-(N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid ChemIDplus
Registry Number Type Source
34441-14-0 CAS Registry Number ChemIDplus
Last Modified
10 March 2014
General Comment
2007-05-01 The non-stereospecific name 'nicotianamine' is used in the literature as a synonym for the naturally occurring (S,S,S) stereoisomer.