(2S)-5-oxopyrrolidine-2-carboxylic acid; 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol

• ChemBase ID: 172799
• Molecular Formular: C13H18N2O6
• Molecular Mass: 298.29182
• Monoisotopic Mass: 298.11648631
• SMILES: c1c(c(c(c(n1)C)O)CO)CO.N1C(=O)CC[C@H]1C(=O)O
• Canonical SMILES: O=C1CC[C@H](N1)C(=O)O.OCc1c(CO)cnc(c1O)C
• InChI: InChI=1S/C8H11NO3.C5H7NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5;7-4-2-1-3(6-4)5(8)9/h2,10-12H,3-4H2,1H3;3H,1-2H2,(H,6,7)(H,8,9)/t;3-/m.0/s1
• InChIKey: RYKKQQUKJJGFMN-HVDRVSQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-oxopyrrolidine-2-carboxylic acid; 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
• IUPAC Traditional name: pyridoxine; pyroglutamic acid
• Synonyms: 5-Hydroxy-6-methyl-3,4-pyridinedimethanol, 5-Oxo-L-proline; Metadoxil; Metasin; Metadoxine

Database IDs

• CAS Number: 74536-44-0
• PubChem SID: 164228709
• PubChem CID: 115198

CALCULATED PROPERTIES

• Acid pKa: 9.39743
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.2796693
• LogD (pH = 7.4): -0.96294767
• Log P: -0.9513213
• Molar Refractivity: 44.1053 cm^3
• Polarizability: 16.756275 Å^3
• Polar Surface Area: 73.58 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 102-104°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M258765

Used for treating patients for liver functional disorders in performing stomatologic interventions and in treatment of acute and chronic alcoholism.

REFERENCES

• Reddy, B., et al.: Cancer Res., 53, 3493 (1993)
• Kim, S., et al.: J. Pharm. Pharmacol., 47, 678 (1993)
• Kono, H., et al.: J. Pharmacol. Exp. Ther., 293, 296 (1993)
• Zang, M., et al.: J. Biol. Chem., 279, 47898 (1993)
• Gonzalez, F., et al.: Mutat. Res., 56