Nicotianamine

Nicotianamine is a metal-chelating molecule ubiquitous in higher plants.[1] Biochemically, it is synthesized by the enzyme nicotianamine synthase, which uses three molecules of S-adenosylmethionine.[2]

Nicotianamine

Names
IUPAC name 1-{3-[(3-amino-3-carboxypropyl)amino]-3-carboxypropyl}azetidine-2-carboxylic acid
Identifiers
CAS Number	34441-14-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17721
ChemSpider	8058557
PubChem CID	7705
UNII	2OGX6YHQ1F
CompTox Dashboard (EPA)	DTXSID8037677
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 Key: KRGPXXHMOXVMMM-CIUDSAMLSA-N
SMILES C1CN([C@@H]1C(=O)O)CC[C@@H](C(=O)O)NCC[C@@H](C(=O)O)N
Properties
Chemical formula	C12H21N3O6
Molar mass	303.31164 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References

1. Takahashi M, Terada Y, Nakai I, Nakanishi H, Yoshimura E, Mori S, Nishizawa NK (2003). "Role of nicotianamine in the intracellular delivery of metals and plant reproductive development". The Plant Cell. 15 (6): 1263–80. doi:10.1105/tpc.010256. PMC 156365. PMID 12782722.
2. Zheng L, Cheng Z, Ai C, Jiang X, Bei X, Zheng Y, Glahn RP, Welch RM, Miller DD, Lei XG, Shou H (2010). "Nicotianamine, a novel enhancer of rice iron bioavailability to humans". PLOS ONE. 5 (4): e10190. Bibcode:2010PLoSO...510190Z. doi:10.1371/journal.pone.0010190. PMC 2855712. PMID 20419136.