benzyl N-[(1S)-2-(4-hydroxyphenyl)-1-{[(2S)-3-oxobutan-2-yl]carbamoyl}ethyl]carbamate

• ChemBase ID: 6377
• Molecular Formular: C21H24N2O5
• Molecular Mass: 384.42566
• Monoisotopic Mass: 384.16852188
• SMILES: C(=O)(N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](C)C(=O)C)OCc1ccccc1
• Canonical SMILES: O=C(N[C@H](C(=O)N[C@H](C(=O)C)C)Cc1ccc(cc1)O)OCc1ccccc1
• InChI: InChI=1S/C21H24N2O5/c1-14(15(2)24)22-20(26)19(12-16-8-10-18(25)11-9-16)23-21(27)28-13-17-6-4-3-5-7-17/h3-11,14,19,25H,12-13H2,1-2H3,(H,22,26)(H,23,27)/t14-,19-/m0/s1
• InChIKey: CLDDOKCDXBMMKZ-LIRRHRJNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-2-(4-hydroxyphenyl)-1-{[(2S)-3-oxobutan-2-yl]carbamoyl}ethyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-2-(4-hydroxyphenyl)-1-{[(2S)-3-oxobutan-2-yl]carbamoyl}ethyl]carbamate
• Synonyms: BENZOYL-TYROSINE-ALANINE-METHYL KETONE

Database IDs

• PubChem SID: 162103398
• PubChem CID: 46937178

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.503573
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.7297244
• LogD (pH = 7.4): 2.7263792
• Log P: 2.729767
• Molar Refractivity: 103.6257 cm^3
• Polarizability: 40.29695 Å^3
• Polar Surface Area: 104.73 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.47
• LOG S: -4.33
• Solubility (Water): 1.82e-02 g/l

DETAILS

DrugBank - DB08775

Drug information: experimental