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

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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 0
Average Mass 303.31160
Monoisotopic Mass 303.143
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).
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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
Manual Xrefs Databases
C00016287 KNApSAcK
C05324 KEGG COMPOUND
CPD-463 MetaCyc
Nicotianamine Wikipedia
View more database links
Registry Numbers Types Sources
34441-14-0 CAS Registry Number KEGG COMPOUND
34441-14-0 CAS Registry Number ChemIDplus
8163098 Beilstein Registry Number Beilstein
8163098 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16245165 PubMed citation Europe PMC
18823453 PubMed citation Europe PMC
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.