(S,S,S)-nicotianamine (CHEBI:17721)

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ChEBI Name	(S,S,S)-nicotianamine

ChEBI ID	CHEBI:17721

ChEBI ASCII Name	(S,S,S)-nicotianamine

Definition	The (S,S,S)-stereoisomer of nicotianamine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:7555, CHEBI:14644

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Formulae

C12H21N3O6
C12H21N3O6

Net Charge

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)/t7-,8-,9-/m0/s1

InChIKey

KRGPXXHMOXVMMM-CIUDSAMLSA-N

SMILES

N[C@@H](CCN[C@@H](CCN1CC[C@H]1C(O)=O)C(O)=O)C(O)=O

Roles Classification
Chemical Role(s):	chelator A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate. 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):	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. 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 )

Application(s):	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).

ChEBI Ontology
Outgoing	(S,S,S)-nicotianamine (CHEBI:17721) has functional parent (S)-azetidine-2-carboxylic acid (CHEBI:6198) (S,S,S)-nicotianamine (CHEBI:17721) has role chelator (CHEBI:38161) (S,S,S)-nicotianamine (CHEBI:17721) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457) (S,S,S)-nicotianamine (CHEBI:17721) has role plant metabolite (CHEBI:76924) (S,S,S)-nicotianamine (CHEBI:17721) is a nicotianamine (CHEBI:25520) (S,S,S)-nicotianamine (CHEBI:17721) is conjugate acid of (S,S,S)-nicotianamine monoanion (CHEBI:62921) (S,S,S)-nicotianamine (CHEBI:17721) is enantiomer of (R,R,R)-nicotianamine (CHEBI:38113) (S,S,S)-nicotianamine (CHEBI:17721) is tautomer of (S,S,S)-nicotianamine trizwitterion (CHEBI:58249)

Incoming	(S,S,S)-nicotianamine monoanion (CHEBI:62921) is conjugate base of (S,S,S)-nicotianamine (CHEBI:17721) (R,R,R)-nicotianamine (CHEBI:38113) is enantiomer of (S,S,S)-nicotianamine (CHEBI:17721) (S,S,S)-nicotianamine trizwitterion (CHEBI:58249) is tautomer of (S,S,S)-nicotianamine (CHEBI:17721)

IUPAC Name

(2S)-1-[(3S)-3-{[(3S)-3-amino-3-carboxypropyl]amino}-3-carboxypropyl]azetidine-2-carboxylic acid

Synonym	Source
Nicotianamine	KEGG COMPOUND

Last Modified

28 July 2014

General Comment
2007-04-23	The non-stereospecific name 'nicotianamine' is used in the literature as a synonym for the naturally occurring stereoisomer.