2-{4-[(2R)-2-({[(1R)-1-carboxy-2-phenylethyl]carbamoyl}amino)-2-(pentylcarbamoyl)ethyl]phenoxy}propanedioic acid

• ChemBase ID: 2174
• Molecular Formular: C27H33N3O9
• Molecular Mass: 543.56562
• Monoisotopic Mass: 543.22167965
• SMILES: CCCCCNC(=O)[C@@H](Cc1ccc(OC(C(=O)O)C(=O)O)cc1)NC(=O)N[C@H](Cc1ccccc1)C(=O)O
• Canonical SMILES: CCCCCNC(=O)[C@@H](Cc1ccc(cc1)OC(C(=O)O)C(=O)O)NC(=O)N[C@@H](C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C27H33N3O9/c1-2-3-7-14-28-23(31)20(15-18-10-12-19(13-11-18)39-22(25(34)35)26(36)37)29-27(38)30-21(24(32)33)16-17-8-5-4-6-9-17/h4-6,8-13,20-22H,2-3,7,14-16H2,1H3,(H,28,31)(H,32,33)(H,34,35)(H,36,37)(H2,29,30,38)/t20-,21-/m1/s1
• InChIKey: BKONADSQADEJJP-NHCUHLMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[(2R)-2-({[(1R)-1-carboxy-2-phenylethyl]carbamoyl}amino)-2-(pentylcarbamoyl)ethyl]phenoxy}propanedioic acid
• IUPAC Traditional name: 2-{4-[(2R)-2-({[(1R)-1-carboxy-2-phenylethyl]carbamoyl}amino)-2-(pentylcarbamoyl)ethyl]phenoxy}propanedioic acid
• Synonyms: 2-{4-[(2s)-2-[({[(1s)-1-Carboxy-2-Phenylethyl]Amino}Carbonyl)Amino]-3-Oxo-3-(Pentylamino)Propyl]Phenoxy}Malonic Acid

Database IDs

• PubChem SID: 46506177; 160965628
• PubChem CID: 46936382

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.3167417
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.2056513
• LogD (pH = 7.4): -5.9410872
• Log P: 2.9894974
• Molar Refractivity: 137.0524 cm^3
• Polarizability: 53.465603 Å^3
• Polar Surface Area: 191.36 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.05
• LOG S: -4.98
• Solubility (Water): 5.67e-03 g/l

DETAILS

DrugBank - DB02436

Drug information: experimental