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

• ChemBase ID: 169471
• Molecular Formular: C11H21NO7
• Molecular Mass: 279.28694
• Monoisotopic Mass: 279.13180202
• SMILES: [C@@H]1([C@H]([C@@H](C(OC1)(O)CN[C@H](C(C)C)C(=O)O)O)O)O
• Canonical SMILES: CC([C@H](C(=O)O)NCC1(O)OC[C@H]([C@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C11H21NO7/c1-5(2)7(10(16)17)12-4-11(18)9(15)8(14)6(13)3-19-11/h5-9,12-15,18H,3-4H2,1-2H3,(H,16,17)/t6-,7-,8-,9+,11?/m1/s1
• InChIKey: LXTJQOKOTMRERV-MUSVHDJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-methyl-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid
• IUPAC Traditional name: (2R)-3-methyl-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)butanoic acid
• Synonyms: N-(1-Deoxy-D-fructos-1-yl)-L-valine; D-1-[(L-1-Carboxy-2-methylpropyl)amino]-1-deoxy-fructose; 1-Deoxy-1-L-valino-D-fructose; 1-L-Valine-1-deoxy-D-fructose; Fructosyl-valine; N-Fructosyl Valine; Fructose Valine (mixture of diastereomers)

Database IDs

• CAS Number: 10003-64-2
• PubChem SID: 162263603
• PubChem CID: 71316985

CALCULATED PROPERTIES

• Acid pKa: 1.596458
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.9684277
• LogD (pH = 7.4): -3.983744
• Log P: -3.9683883
• Molar Refractivity: 62.367 cm^3
• Polarizability: 25.714369 Å^3
• Polar Surface Area: 139.48 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Beige Solid
• Melting Point: 138-140°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F792595

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)
• Sosnovsky, G., et al.: J. Pharm. Sci., 82, 649 (1991)
• Glinsky, G., et al.: Cancer Res., 56, 5319 (1991)