2-{[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl](methyl)amino}butanedioic acid

• ChemBase ID: 177845
• Molecular Formular: C13H17NO6
• Molecular Mass: 283.27718
• Monoisotopic Mass: 283.10558727
• SMILES: c1(cccc(c1)[C@H](CN(C(CC(=O)O)C(=O)O)C)O)O
• Canonical SMILES: OC(=O)CC(N(C[C@@H](c1cccc(c1)O)O)C)C(=O)O
• InChI: InChI=1S/C13H17NO6/c1-14(10(13(19)20)6-12(17)18)7-11(16)8-3-2-4-9(15)5-8/h2-5,10-11,15-16H,6-7H2,1H3,(H,17,18)(H,19,20)/t10?,11-/m0/s1
• InChIKey: NILXUFZCPICFBR-DTIOYNMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl](methyl)amino}butanedioic acid
• IUPAC Traditional name: 2-{[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl](methyl)amino}butanedioic acid
• Synonyms: N-[(2R)-2-Hydroxy-2-(3-hydroxyphenyl)ethyl]-N-methylaspartic Acid; N-(2-Succinyl) Phenylephrine(Mixture of Diastereomers)

Database IDs

• CAS Number: 915278-80-7
• PubChem SID: 164233755
• PubChem CID: 71752228

CALCULATED PROPERTIES

• Acid pKa: 1.1294371
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -3.2594676
• LogD (pH = 7.4): -5.0421705
• Log P: -2.3589356
• Molar Refractivity: 69.158 cm^3
• Polarizability: 27.112646 Å^3
• Polar Surface Area: 118.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S688850

The major degradation product identified in Acetaminophen, Phenylephrine hydrochloride, and Chlorpheniramine maleate.

REFERENCES

• Wong, J., et al.: Anal. Chem., 78, 7891 (2006)