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

• ChemBase ID: 175103
• Molecular Formular: C12H21N3O6
• Molecular Mass: 303.31164
• Monoisotopic Mass: 303.14303541
• SMILES: [C@@H]1(CCN1CC[C@H](NCC[C@H](N)C(=O)O)C(=O)O)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CCN[C@H](C(=O)O)CCN1CC[C@@H]1C(=O)O
• 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-XHNCKOQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-[(3S)-3-{[(3S)-3-amino-3-carboxypropyl]amino}-3-carboxypropyl]azetidine-2-carboxylic acid
• IUPAC Traditional name: (R,S,S)-nicotianamine
• Synonyms: (αS,2S)-α-[[(3S)-3-Amino-3-carboxypropyl]amino]-2-carboxy-1-azetidinebutanoic Acid; [2S-[1[αR*(R*)],2R*]]-α-[(3-Amino-3-carboxypropyl)amino]-2-carboxy-1-azetidinebutanoic Acid; Nicotianamine

Database IDs

• CAS Number: 34441-14-0
• PubChem SID: 164231013
• PubChem CID: 13892427

CALCULATED PROPERTIES

• Acid pKa: 1.0491163
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -9.319115
• LogD (pH = 7.4): -9.492592
• Log P: -9.317677
• Molar Refractivity: 70.7792 cm^3
• Polarizability: 28.420774 Å^3
• Polar Surface Area: 153.19 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Beige Solid
• Melting Point: >220°C dec.

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N408500

Phytosiderophores are produced in higher plants as iron chelating amino acids that promote uptake of iron from soil.

REFERENCES

• Klair, S., et al.: J. Plant Nutr., 19, 1295 (1996)