methyl 3-(1H-indol-3-yl)-2-[(E)-(phenylmethylidene)amino]propanoate

• ChemBase ID: 179362
• Molecular Formular: C19H18N2O2
• Molecular Mass: 306.35842
• Monoisotopic Mass: 306.13682783
• SMILES: c1ccc2c(c1)c(c[nH]2)CC(/N=C/c1ccccc1)C(=O)OC
• Canonical SMILES: COC(=O)C(Cc1c[nH]c2c1cccc2)/N=C/c1ccccc1
• InChI: InChI=1S/C19H18N2O2/c1-23-19(22)18(20-12-14-7-3-2-4-8-14)11-15-13-21-17-10-6-5-9-16(15)17/h2-10,12-13,18,21H,11H2,1H3/b20-12+
• InChIKey: LFMPJRXYSNSSJV-UDWIEESQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-(1H-indol-3-yl)-2-[(E)-(phenylmethylidene)amino]propanoate
• IUPAC Traditional name: methyl 3-(1H-indol-3-yl)-2-[(E)-(phenylmethylidene)amino]propanoate
• Synonyms: N-(Phenylmethylene)-D,L-tryptophan Methyl Ester; N-Benzylidenetryptophan Methyl Ester; D,L-Tryptophan Methyl Ester Benzaldimine

Database IDs

• CAS Number: 19779-75-0
• PubChem SID: 164235272
• PubChem CID: 2728112

CALCULATED PROPERTIES

• Acid pKa: 16.138514
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.8623712
• LogD (pH = 7.4): 3.8697212
• Log P: 3.8698156
• Molar Refractivity: 90.6489 cm^3
• Polarizability: 35.84981 Å^3
• Polar Surface Area: 54.45 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Light Yellow Solid
• Melting Point: 125-126°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T894850

Optically active α-amino acid derivative.

REFERENCES

• Madalengoitia, J., et al.: Biochem. Med. Chem., 5, 1807 (1997)