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

• ChemBase ID: 2268
• Molecular Formular: C20H22N2O6
• Molecular Mass: 386.39848
• Monoisotopic Mass: 386.14778643
• SMILES: Cc1ccc(OC/C(=C/C=O)/Nc2cc(C[C@H](N)C(=O)O)c(O)cc2O)cc1
• Canonical SMILES: O=C/C=C(\Nc1cc(C[C@@H](C(=O)O)N)c(cc1O)O)/COc1ccc(cc1)C
• InChI: InChI=1S/C20H22N2O6/c1-12-2-4-15(5-3-12)28-11-14(6-7-23)22-17-9-13(8-16(21)20(26)27)18(24)10-19(17)25/h2-7,9-10,16,22,24-25H,8,11,21H2,1H3,(H,26,27)/b14-6-/t16-/m0/s1
• InChIKey: FSNBWEOGSXUNGF-VCXBKZMZSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 46509095; 160965721
• PubChem CID: 46936418

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.6904135
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.67389154
• LogD (pH = 7.4): -0.68619496
• Log P: -0.6739112
• Molar Refractivity: 106.0182 cm^3
• Polarizability: 39.507492 Å^3
• Polar Surface Area: 142.11 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.37
• LOG S: -4.05
• Solubility (Water): 3.42e-02 g/l

DETAILS

DrugBank - DB02537

Drug information: experimental