(2S)-2-amino-3-(2,4-dihydroxy-5-{[(2E)-1-(naphthalen-2-yloxy)-4-oxobut-2-en-2-yl]amino}phenyl)propanoic acid

• ChemBase ID: 2243
• Molecular Formular: C23H22N2O6
• Molecular Mass: 422.43058
• Monoisotopic Mass: 422.14778643
• SMILES: N[C@@H](Cc1c(O)cc(O)c(c1)N/C(=C/C=O)/COc1ccc2ccccc2c1)C(=O)O
• Canonical SMILES: O=C/C=C(/Nc1cc(C[C@@H](C(=O)O)N)c(cc1O)O)\COc1ccc2c(c1)cccc2
• InChI: InChI=1S/C23H22N2O6/c24-19(23(29)30)10-16-11-20(22(28)12-21(16)27)25-17(7-8-26)13-31-18-6-5-14-3-1-2-4-15(14)9-18/h1-9,11-12,19,25,27-28H,10,13,24H2,(H,29,30)/b17-7+/t19-/m0/s1
• InChIKey: PZWMZAFFUAWVDN-CQXYXCHQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(2,4-dihydroxy-5-{[(2E)-1-(naphthalen-2-yloxy)-4-oxobut-2-en-2-yl]amino}phenyl)propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-(2,4-dihydroxy-5-{[(2E)-1-(naphthalen-2-yloxy)-4-oxobut-2-en-2-yl]amino}phenyl)propanoic acid
• Synonyms: 2-Hydroxy-5-({1-[(2-Naphthyloxy)Methyl]-3-Oxoprop-1-Enyl}Amino)Tyrosine

Database IDs

• PubChem SID: 46507750; 160965696
• PubChem CID: 17754104

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.6904135
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.19783612
• LogD (pH = 7.4): -0.2101396
• Log P: -0.19785586
• Molar Refractivity: 117.4272 cm^3
• Polarizability: 45.201202 Å^3
• Polar Surface Area: 142.11 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.7
• LOG S: -4.77
• Solubility (Water): 7.14e-03 g/l

DETAILS

DrugBank - DB02511

Drug information: experimental