(2R)-1-{[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}pyrrolidine-2-carboxylic acid

• ChemBase ID: 169469
• Molecular Formular: C11H19NO7
• Molecular Mass: 277.27106
• Monoisotopic Mass: 277.11615195
• SMILES: [C@@H]1([C@H]([C@@H](C(OC1)(O)CN1[C@H](CCC1)C(=O)O)O)O)O
• Canonical SMILES: O[C@@H]1COC([C@H]([C@@H]1O)O)(O)CN1CCC[C@@H]1C(=O)O
• InChI: InChI=1S/C11H19NO7/c13-7-4-19-11(18,9(15)8(7)14)5-12-3-1-2-6(12)10(16)17/h6-9,13-15,18H,1-5H2,(H,16,17)/t6-,7-,8-,9+,11?/m1/s1
• InChIKey: WDZMFMTVJVHSKA-MUSVHDJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-{[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2R)-1-{[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}pyrrolidine-2-carboxylic acid
• Synonyms: 1-(1-Deoxy-D-fructos-1-yl)-L-proline; (S)-1-(2-Carboxy-1-pyrrolidinyl)-1-deoxy-D-fructose; 1-Deoxy-1-L-proline-D-fructose; 1-Deoxy-1-L-prolino-D-fructose; Fructose-proline (mixture of diastereomers)

Database IDs

• CAS Number: 29118-61-4
• PubChem SID: 162263601
• PubChem CID: 71316983

CALCULATED PROPERTIES

• Acid pKa: 2.8670459
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.5018945
• LogD (pH = 7.4): -5.0345583
• Log P: -4.490902
• Molar Refractivity: 61.4585 cm^3
• Polarizability: 25.018394 Å^3
• Polar Surface Area: 130.69 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: 48-50°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - F792565

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)