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

• ChemBase ID: 169467
• Molecular Formular: C12H23NO7
• Molecular Mass: 293.31352
• Monoisotopic Mass: 293.14745208
• SMILES: [C@@H]1([C@H]([C@@H](C(OC1)(O)CN[C@H](CC(C)C)C(=O)O)O)O)O
• Canonical SMILES: CC(C[C@H](C(=O)O)NCC1(O)OC[C@H]([C@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C12H23NO7/c1-6(2)3-7(11(17)18)13-5-12(19)10(16)9(15)8(14)4-20-12/h6-10,13-16,19H,3-5H2,1-2H3,(H,17,18)/t7-,8-,9-,10+,12?/m1/s1
• InChIKey: ZVFBUGZJZNDPOS-OQQZPARHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-4-methyl-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)pentanoic acid
• IUPAC Traditional name: (2R)-4-methyl-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)pentanoic acid
• Synonyms: N-(1-Deoxy-D-fructos-1-yl)-L-leucine; (S)-1-[(1-Carboxy-3-methylbutyl)amino]-1-deoxy-D-fructose; D-1-[(L-1-Carboxy-3-methylbutyl)amino]-1-deoxy-fructose; 1-Deoxy-1-L-leucino-D-fructose; Fructoseleucine; Fructose-leucine (mixture of diastereomers)

Database IDs

• CAS Number: 34393-18-5
• PubChem SID: 162263599
• PubChem CID: 71316981

CALCULATED PROPERTIES

• Acid pKa: 1.6700094
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.6013098
• LogD (pH = 7.4): -3.6186895
• Log P: -3.6012697
• Molar Refractivity: 67.045 cm^3
• Polarizability: 27.527864 Å^3
• Polar Surface Area: 139.48 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >100°C (dec.)

Safety Information

• Storage Condition: Refrigerator, under inert atmosphere

DETAILS

Toronto Research Chemicals - F792540

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)