(2R)-3-(1H-indol-3-yl)-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)propanoic acid

• ChemBase ID: 169470
• Molecular Formular: C17H22N2O7
• Molecular Mass: 366.36578
• Monoisotopic Mass: 366.14270105
• SMILES: [C@@H]1([C@H]([C@@H](C(OC1)(O)CN[C@H](Cc1c[nH]c2c1cccc2)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NCC1(O)OC[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C17H22N2O7/c20-13-7-26-17(25,15(22)14(13)21)8-19-12(16(23)24)5-9-6-18-11-4-2-1-3-10(9)11/h1-4,6,12-15,18-22,25H,5,7-8H2,(H,23,24)/t12-,13-,14-,15+,17?/m1/s1
• InChIKey: OUEOJKVGJOCAHT-WQYWAISESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 25020-15-9
• PubChem SID: 162263602
• PubChem CID: 71316984

CALCULATED PROPERTIES

• Acid pKa: 1.6867067
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -3.100321
• LogD (pH = 7.4): -3.1171038
• Log P: -3.100291
• Molar Refractivity: 89.0769 cm^3
• Polarizability: 36.655144 Å^3
• Polar Surface Area: 155.27 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Light Tan to Yellow Solid
• Melting Point: >125°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F792580

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)