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

• ChemBase ID: 169468
• Molecular Formular: C15H21NO7
• Molecular Mass: 327.32974
• Monoisotopic Mass: 327.13180202
• SMILES: [C@@H]1([C@H]([C@@H](C(OC1)(O)CN[C@H](Cc1ccccc1)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@@H](Cc1ccccc1)NCC1(O)OC[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H21NO7/c17-11-7-23-15(22,13(19)12(11)18)8-16-10(14(20)21)6-9-4-2-1-3-5-9/h1-5,10-13,16-19,22H,6-8H2,(H,20,21)/t10-,11-,12-,13+,15?/m1/s1
• InChIKey: CPXVOVGNKRERLG-PSSVGPPCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-phenyl-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)propanoic acid
• IUPAC Traditional name: (2R)-3-phenyl-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)propanoic acid
• Synonyms: N-(1-Deoxy-D-fructos-1-yl)-L-phenylalanine; (S)-1-[(1-Carboxy-2-phenylethyl)amino]-1-deoxy-D-fructose; 1-[(α-Carboxyphenethyl)amino]-1-deoxy-fructose; N-(1'-Carboxy-2'-phenylethyl)amino-1-deoxyfructose; Fructose-phenylalanine (mixture of diastereomers)

Database IDs

• CAS Number: 31105-03-0
• PubChem SID: 162263600
• PubChem CID: 71316982

CALCULATED PROPERTIES

• Acid pKa: 1.5990334
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.1989434
• LogD (pH = 7.4): -3.2200546
• Log P: -3.1988516
• Molar Refractivity: 77.9904 cm^3
• Polarizability: 31.524578 Å^3
• Polar Surface Area: 139.48 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F792560

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

REFERENCES

• Horiuchi, T., et al.: Agric. Biol. Chem., 55, 333 (1991)
• Glinsky, G., et al.: Cancer Res., 56, 5319 (1991)