(2S)-6-{[(benzyloxy)carbonyl]amino}-2-[bis(carboxymethyl)amino]hexanoic acid

• ChemBase ID: 163628
• Molecular Formular: C18H24N2O8
• Molecular Mass: 396.39176
• Monoisotopic Mass: 396.15326574
• SMILES: C(CCC[C@H](N(CC(=O)O)CC(=O)O)C(=O)O)NC(=O)OCc1ccccc1
• Canonical SMILES: O=C(OCc1ccccc1)NCCCC[C@@H](C(=O)O)N(CC(=O)O)CC(=O)O
• InChI: InChI=1S/C18H24N2O8/c21-15(22)10-20(11-16(23)24)14(17(25)26)8-4-5-9-19-18(27)28-12-13-6-2-1-3-7-13/h1-3,6-7,14H,4-5,8-12H2,(H,19,27)(H,21,22)(H,23,24)(H,25,26)/t14-/m0/s1
• InChIKey: RKSASMXBVVMAAS-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-{[(benzyloxy)carbonyl]amino}-2-[bis(carboxymethyl)amino]hexanoic acid
• IUPAC Traditional name: (2S)-6-{[(benzyloxy)carbonyl]amino}-2-[bis(carboxymethyl)amino]hexanoic acid
• Synonyms: N2,N2-Bis(carboxymethyl)-N6-[(phenylmethoxy)carbonyl]lysine; N-(5-Carbobenzyloxyamino)-1-carboxypentyl)iminodiacetic Acid; N6-Carbobenzyloxy-N2,N2-bis(carboxymethyl)lysine; N2,N2-Bis(carboxymethyl)-N6-[(phenylmethoxy)carbonyl]-L-lysine; N6-Carbobenzyloxy-N2,N2-bis(carboxymethyl)-L-lysine

Database IDs

• CAS Number: 113231-04-2; 209052-01-7
• PubChem SID: 162257763
• PubChem CID: 7072723

CALCULATED PROPERTIES

• Acid pKa: 3.0061226
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.012129
• LogD (pH = 7.4): -8.314079
• Log P: 0.19809338
• Molar Refractivity: 95.728 cm^3
• Polarizability: 37.589073 Å^3
• Polar Surface Area: 153.47 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 165-170°C; 173-175°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C175935

It is used in the synthesis of nickel-chelating fluorinated lipids for protein monolayer crystallizations.

Toronto Research Chemicals - C175930

It is used in the synthesis of nickel-chelating fluorinated lipids for protein monolayer crystallizations.

REFERENCES

• Vince, R., et al.: J. Med. Chem., 14, 402 (1971)
• Melander, W., et al.: Arch. Biochem. Biophys., 183, 200 (1971)
• Vince, R., et al.: J. Med. Chem., 14, 402 (1971)
• Melander, W., et al.: Arch. Biochem. Biophys., 183, 200 (1971)