(2E)-2-{[(2S)-2-carboxy-2-(2-phenoxyacetamido)ethoxy]imino}pentanedioic acid

• ChemBase ID: 6017
• Molecular Formular: C16H18N2O9
• Molecular Mass: 382.32212
• Monoisotopic Mass: 382.10123017
• SMILES: OC(=O)CC/C(=N\OC[C@@H](C(=O)O)NC(=O)COc1ccccc1)/C(=O)O
• Canonical SMILES: OC(=O)[C@@H](NC(=O)COc1ccccc1)CO/N=C(/C(=O)O)\CCC(=O)O
• InChI: InChI=1S/C16H18N2O9/c19-13(9-26-10-4-2-1-3-5-10)17-12(16(24)25)8-27-18-11(15(22)23)6-7-14(20)21/h1-5,12H,6-9H2,(H,17,19)(H,20,21)(H,22,23)(H,24,25)/b18-11+/t12-/m0/s1
• InChIKey: LDNKNKRRFZRLIG-HWQJWEFDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-{[(2S)-2-carboxy-2-(2-phenoxyacetamido)ethoxy]imino}pentanedioic acid
• IUPAC Traditional name: (2E)-2-{[(2S)-2-carboxy-2-(2-phenoxyacetamido)ethoxy]imino}pentanedioic acid
• Synonyms: (2E)-2-({(2S)-2-CARBOXY-2-[(PHENOXYACETYL)AMINO]ETHOXY}IMINO)PENTANEDIOIC ACID

Database IDs

• PubChem SID: 160969442; 99444872
• PubChem CID: 16741209

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.8308423
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -5.5804353
• LogD (pH = 7.4): -9.544656
• Log P: 0.50688314
• Molar Refractivity: 86.3726 cm^3
• Polarizability: 33.94268 Å^3
• Polar Surface Area: 171.82 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.1
• LOG S: -3.59
• Solubility (Water): 9.79e-02 g/l

DETAILS

DrugBank - DB08401

Drug information: experimental