(2R)-2-[(4-carbamimidoylphenyl)amino]-2-{5-ethoxy-2-fluoro-3-[(3R)-oxolan-3-yloxy]phenyl}acetic acid

• ChemBase ID: 4155
• Molecular Formular: C21H24FN3O5
• Molecular Mass: 417.4307632
• Monoisotopic Mass: 417.1699991
• SMILES: N=C(N)c1ccc(N[C@@H](C(=O)O)c2c(F)c(O[C@@H]3CCOC3)cc(OCC)c2)cc1
• Canonical SMILES: CCOc1cc([C@H](C(=O)O)Nc2ccc(cc2)C(=N)N)c(c(c1)O[C@H]1COCC1)F
• InChI: InChI=1S/C21H24FN3O5/c1-2-29-15-9-16(18(22)17(10-15)30-14-7-8-28-11-14)19(21(26)27)25-13-5-3-12(4-6-13)20(23)24/h3-6,9-10,14,19,25H,2,7-8,11H2,1H3,(H3,23,24)(H,26,27)/t14-,19-/m1/s1
• InChIKey: PGYOHIAQCFZQDK-AUUYWEPGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(4-carbamimidoylphenyl)amino]-2-{5-ethoxy-2-fluoro-3-[(3R)-oxolan-3-yloxy]phenyl}acetic acid
• IUPAC Traditional name: (R)-[(4-carbamimidoylphenyl)amino]({5-ethoxy-2-fluoro-3-[(3R)-oxolan-3-yloxy]phenyl})acetic acid
• Synonyms: (2R)-({4-[AMINO(IMINO)METHYL]PHENYL}AMINO){5-ETHOXY-2-FLUORO-3-[(3R)-TETRAHYDROFURAN-3-YLOXY]PHENYL}ACETICACID

Database IDs

• PubChem SID: 160967587; 46505729
• PubChem CID: 6852220

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7787123
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.21454158
• LogD (pH = 7.4): 0.2212823
• Log P: 0.22133793
• Molar Refractivity: 119.8683 cm^3
• Polarizability: 41.06607 Å^3
• Polar Surface Area: 126.89 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.01
• LOG S: -4.15
• Solubility (Water): 2.96e-02 g/l

DETAILS

DrugBank - DB04590

Drug information: experimental