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

• ChemBase ID: 169466
• Molecular Formular: C10H18N2O8
• Molecular Mass: 294.25852
• Monoisotopic Mass: 294.10631555
• SMILES: [C@@H]1([C@H]([C@@H](C(OC1)(O)CN[C@H](CC(=O)N)C(=O)O)O)O)O
• Canonical SMILES: NC(=O)C[C@H](C(=O)O)NCC1(O)OC[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C10H18N2O8/c11-6(14)1-4(9(17)18)12-3-10(19)8(16)7(15)5(13)2-20-10/h4-5,7-8,12-13,15-16,19H,1-3H2,(H2,11,14)(H,17,18)/t4-,5-,7-,8+,10?/m1/s1
• InChIKey: AOBQWGHMIKNEHI-CWOUCCJVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-carbamoyl-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)propanoic acid
• IUPAC Traditional name: (2R)-3-carbamoyl-2-({[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}amino)propanoic acid
• Synonyms: N2-(1-Deoxy-D-fructos-1-yl)-L-asparagine; (S)-1-[(3-Amino-1-carboxy-3-oxopropyl)amino]-1-deoxy-D-fructose; 1-[(2-Carbamoyl-1-carboxyethyl)amino]-1-deoxy-fructose; 1-Deoxy-1-L-asparagino-D-fructose; N-(1-Deoxy-D-fructosyl)-L-asparagine; Fructose-asparagine(Mixture of diastereomers)

Database IDs

• CAS Number: 34393-27-6
• PubChem SID: 162263598
• PubChem CID: 71316980

CALCULATED PROPERTIES

• Acid pKa: 1.3522668
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -6.3007803
• LogD (pH = 7.4): -6.3881173
• Log P: -6.299974
• Molar Refractivity: 61.229 cm^3
• Polarizability: 25.260098 Å^3
• Polar Surface Area: 182.57 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Pale Yellow Solid
• Melting Point: >190°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - F792525

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