(2R)-2-[(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanamido]pentanedioic acid

• ChemBase ID: 169650
• Molecular Formular: C11H19NO10
• Molecular Mass: 325.26926
• Monoisotopic Mass: 325.10089581
• SMILES: C(C[C@@H](NC(=O)[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)C(=O)O)C(=O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]([C@H](C(=O)N[C@@H](C(=O)O)CCC(=O)O)O)O)O)O
• InChI: InChI=1S/C11H19NO10/c13-3-5(14)7(17)8(18)9(19)10(20)12-4(11(21)22)1-2-6(15)16/h4-5,7-9,13-14,17-19H,1-3H2,(H,12,20)(H,15,16)(H,21,22)/t4-,5-,7-,8+,9-/m1/s1
• InChIKey: RALMEYHIPGGEHB-WPRMSWRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanamido]pentanedioic acid
• IUPAC Traditional name: (2R)-2-[(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanamido]pentanedioic acid
• Synonyms: N-D-Gluconoyl-L-glutamic Acid

Database IDs

• CAS Number: 93980-76-8
• PubChem SID: 162263782
• PubChem CID: 71317082

CALCULATED PROPERTIES

• Acid pKa: 3.2027721
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -8.1148205
• LogD (pH = 7.4): -10.956094
• Log P: -4.299414
• Molar Refractivity: 66.3588 cm^3
• Polarizability: 26.915358 Å^3
• Polar Surface Area: 204.85 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G417500

It is used in the synthesis of glyconyl peptides.

REFERENCES

• Doherty, D.G., et al.: J. Biol. Chem., 201, 857 (1953)