4-{[(1S)-1-[(9-oxo-9,10-dihydroacridin-2-yl)carbamoyl]-2-phenylethyl]carbamoyl}butanoic acid

• ChemBase ID: 157996
• Molecular Formular: C27H25N3O5
• Molecular Mass: 471.5045
• Monoisotopic Mass: 471.17942092
• SMILES: c1ccc(cc1)C[C@@H](C(=O)Nc1ccc2c(c1)c(=O)c1ccccc1[nH]2)NC(=O)CCCC(=O)O
• Canonical SMILES: O=C(N[C@H](C(=O)Nc1ccc2c(c1)c(=O)c1c([nH]2)cccc1)Cc1ccccc1)CCCC(=O)O
• InChI: InChI=1S/C27H25N3O5/c31-24(11-6-12-25(32)33)30-23(15-17-7-2-1-3-8-17)27(35)28-18-13-14-22-20(16-18)26(34)19-9-4-5-10-21(19)29-22/h1-5,7-10,13-14,16,23H,6,11-12,15H2,(H,28,35)(H,29,34)(H,30,31)(H,32,33)/t23-/m0/s1
• InChIKey: ARQVOICOWZVNEP-QHCPKHFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(1S)-1-[(9-oxo-9,10-dihydroacridin-2-yl)carbamoyl]-2-phenylethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: 4-{[(1S)-1-[(9-oxo-10H-acridin-2-yl)carbamoyl]-2-phenylethyl]carbamoyl}butanoic acid
• Synonyms: N-(N-Glutaryl-L-phenylalanyl)-2-aminoacridone

Database IDs

• CAS Number: 115930-63-7
• MDL Number: MFCD01863061
• PubChem SID: 162252132; 24873119
• PubChem CID: 16213677

CALCULATED PROPERTIES

• Acid pKa: 4.0676455
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 3.3815699
• LogD (pH = 7.4): 1.7072254
• Log P: 4.826228
• Molar Refractivity: 131.3354 cm^3
• Polarizability: 49.63739 Å^3
• Polar Surface Area: 124.6 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble
• Melting Point: 272 °C(lit.)
• Fluorescence: λex 398 nm; λem 440 nm in 0.1 M Tris pH 8.0 (fluoroescence decreases upon cleavage with α-chymotrypsin)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C27H25N3O5

DETAILS

Sigma Aldrich - 49742

Analysis Note
In addition to the emission maximum at 440 nm, there is a lower maxima at 463 nm.
Application
suitable as spectrophotometric substrate for α-chymotrypsin (linear increase in absorbance at 450 nm)
Other Notes
Substrate for the continuous assay of α-chymotrypsin at wavelengths 450/570nm1