sodium 4-[(2S)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoate

• ChemBase ID: 132931
• Molecular Formular: C23H19N2NaO5
• Molecular Mass: 426.39713
• Monoisotopic Mass: 426.119166
• SMILES: c1ccc(cc1)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)Nc1ccc(cc1)C(=O)[O-].[Na+]
• Canonical SMILES: O=C([C@@H](NC(=O)c1ccccc1)Cc1ccc(cc1)O)Nc1ccc(cc1)C(=O)[O-].[Na+]
• InChI: InChI=1S/C23H20N2O5.Na/c26-19-12-6-15(7-13-19)14-20(25-21(27)16-4-2-1-3-5-16)22(28)24-18-10-8-17(9-11-18)23(29)30;/h1-13,20,26H,14H2,(H,24,28)(H,25,27)(H,29,30);/q;+1/p-1/t20-;/m0./s1
• InChIKey: HEJYVLSWQWPKPQ-BDQAORGHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 4-[(2S)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoate
• IUPAC Traditional name: sodium 4-[(2S)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoate
• Synonyms: N-Benzoyl-L-tyrosyl-4-aminobenzoic acid sodium salt; Bentiromide; N-Benzoyl-L-tyrosine p-amidobenzoic acid sodium salt

Database IDs

• CAS Number: 41748-47-4
• EC Number: 255-530-7
• MDL Number: MFCD00042647
• PubChem SID: 162227208; 24848007
• PubChem CID: 23680486

CALCULATED PROPERTIES

• Acid pKa: 4.157471
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.1798987
• LogD (pH = 7.4): 0.47363257
• Log P: 3.5389557
• Molar Refractivity: 123.5821 cm^3
• Polarizability: 41.927135 Å^3
• Polar Surface Area: 118.56 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: powder
• Melting Point: ~210 °C (dec.)
• Optical Rotation: [α]20/D +45±2°, c = 1% in DMF/H2O 1:1

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1; 3
• Risk Statements: 36/38
• Safety Statements: 26-36
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, HPLC)
• Quality: lyophilized
• Linear Formula: C23H19N2O5Na

DETAILS

Sigma Aldrich - 13135

Other Notes
Hydrolysis of benzol-tyrosyl-p-aminobenzoic acid by a human intestinal microvillar peptidase1; Substrate for the assay of chymotrypsin in crude biological materials.2