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

• ChemBase ID: 165995
• Molecular Formular: C12H20N2O7
• Molecular Mass: 304.2964
• Monoisotopic Mass: 304.12705099
• SMILES: [C@@H]1(CCN1CC[C@H](NCC[C@H](O)C(=O)O)C(=O)O)C(=O)O
• Canonical SMILES: O[C@H](C(=O)O)CCN[C@H](C(=O)O)CCN1CC[C@@H]1C(=O)O
• InChI: InChI=1S/C12H20N2O7/c15-9(12(20)21)1-4-13-7(10(16)17)2-5-14-6-3-8(14)11(18)19/h7-9,13,15H,1-6H2,(H,16,17)(H,18,19)(H,20,21)/t7-,8+,9-/m0/s1
• InChIKey: CUZKLRTTYZOCSD-YIZRAAEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-[(3S)-3-carboxy-3-{[(3S)-3-carboxy-3-hydroxypropyl]amino}propyl]azetidine-2-carboxylic acid
• IUPAC Traditional name: (2R)-1-[(3S)-3-carboxy-3-{[(3S)-3-carboxy-3-hydroxypropyl]amino}propyl]azetidine-2-carboxylic acid
• Synonyms: (αS,2S)-2-Carboxy-α-[[(3S)-3-carboxy-3-hydroxypropyl]amino]-1-azetidinebutanoic Acid; 2'-Dehydroxymugineic Acid; DMA; 2'-Deoxymugineic Acid

Database IDs

• CAS Number: 74235-24-8
• PubChem SID: 162260128
• PubChem CID: 13071820

CALCULATED PROPERTIES

• Acid pKa: 1.0490516
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -8.813163
• LogD (pH = 7.4): -10.370452
• Log P: -7.064278
• Molar Refractivity: 69.1217 cm^3
• Polarizability: 27.590893 Å^3
• Polar Surface Area: 147.4 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: >165°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D243250

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)