benzyl N-[(1S)-1-carbamoyl-2-(1H-indol-3-yl)-2-oxoethyl]carbamate

• ChemBase ID: 161706
• Molecular Formular: C19H17N3O4
• Molecular Mass: 351.35598
• Monoisotopic Mass: 351.12190604
• SMILES: c1ccc2c(c1)c(c[nH]2)C(=O)[C@@H](C(=O)N)NC(=O)OCc1ccccc1
• Canonical SMILES: O=C(N[C@@H](C(=O)c1c[nH]c2c1cccc2)C(=O)N)OCc1ccccc1
• InChI: InChI=1S/C19H17N3O4/c20-18(24)16(22-19(25)26-11-12-6-2-1-3-7-12)17(23)14-10-21-15-9-5-4-8-13(14)15/h1-10,16,21H,11H2,(H2,20,24)(H,22,25)/t16-/m0/s1
• InChIKey: DFBNEEDBMWALFX-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-carbamoyl-2-(1H-indol-3-yl)-2-oxoethyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-carbamoyl-2-(1H-indol-3-yl)-2-oxoethyl]carbamate
• Synonyms: (L)-N-Benzyloxycarbonyl-β-oxo-tryptophaneamide

Database IDs

• CAS Number: 255371-72-3
• PubChem SID: 162255841
• PubChem CID: 57347582

CALCULATED PROPERTIES

• Acid pKa: 12.715821
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 2.0555117
• LogD (pH = 7.4): 2.0555098
• Log P: 2.0555117
• Molar Refractivity: 94.3893 cm^3
• Polarizability: 37.49611 Å^3
• Polar Surface Area: 114.28 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetic Acid; DMF; DMSO; Hot Methanol
• Melting Point: 186-188°C

DETAILS

Toronto Research Chemicals - B285925

An amino acid amide.

REFERENCES

• Smith, E.L., and Polglase, W.J.: J. Biol. Chem., 180, 1209 (1949)