Nicotianamine

Nicotianamine
Names
	Systematic IUPAC name (2S)-1-[(3S)-3-{[(3S)-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

Nicotianamine is a metal-chelating molecule ubiquitous in higher plants.^[1] It is also used as a precursor for the synthesis of phytosiderophores which play a key role in iron uptake from the soil in graminaceous plants.^[2] Biochemically, it is synthesized by the enzyme nicotianamine synthase, which uses three molecules of S-adenosylmethionine.^[3]

References

[1]

[2]

[3]

Names

Systematic IUPAC name (2S)-1-[(3S)-3-{[(3S)-3-Amino-3-carboxypropyl]amino}-3-carboxypropyl]azetidine-2-carboxylic acid
Identifiers
CAS Number	34441-14-0^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17721
ChemSpider	8058557
PubChem CID	7705
UNII	2OGX6YHQ1F^Y
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