(2R)-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)propanoic acid

• ChemBase ID: 169465
• Molecular Formular: C9H17NO7
• Molecular Mass: 251.23378
• Monoisotopic Mass: 251.10050189
• SMILES: [C@@H]1([C@H]([C@@H](C(OC1)(O)CN[C@H](C)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@H](NCC1(O)OC[C@H]([C@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C9H17NO7/c1-4(8(14)15)10-3-9(16)7(13)6(12)5(11)2-17-9/h4-7,10-13,16H,2-3H2,1H3,(H,14,15)/t4-,5-,6-,7+,9?/m1/s1
• InChIKey: UEKCFAIUNCFLEA-XGVUHEBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)propanoic acid
• IUPAC Traditional name: (2R)-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)propanoic acid
• Synonyms: N-(1-Deoxy-D-fructos-1-yl)-L-alanine; (S)-1-[(1-Carboxyethyl)amino]-1-deoxy-D-fructose; 1-Alanino-1-deoxy-D-fructose; 1-Deoxy-1-L-alanine-D-fructose; N-(1-Deoxy-D-fructosyl)-L-alanine; Fructose-alanine (mixture of diastereomers)

Database IDs

• CAS Number: 16124-24-6
• PubChem SID: 162263597
• PubChem CID: 71316979

CALCULATED PROPERTIES

• Acid pKa: 1.4463695
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -4.8553042
• LogD (pH = 7.4): -4.8835692
• Log P: -4.8551173
• Molar Refractivity: 53.3714 cm^3
• Polarizability: 22.099394 Å^3
• Polar Surface Area: 139.48 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: 138-140°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F792520

An Amadori compound having the potential to alter cellular adhesion, inhibit cancer metastasis and induce apoptosis.

REFERENCES

• Hofmann, T., et al.: J. Agric. Food Chem., 47, 379 (1999)