4-{[(1S)-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]-2-phenylethyl]carbamoyl}butanoic acid

• ChemBase ID: 132311
• Molecular Formular: C24H24N2O6
• Molecular Mass: 436.45716
• Monoisotopic Mass: 436.1634365
• SMILES: Cc1cc(=O)oc2c1ccc(c2)NC(=O)[C@H](Cc1ccccc1)NC(=O)CCCC(=O)O
• Canonical SMILES: O=C(N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)Cc1ccccc1)CCCC(=O)O
• InChI: InChI=1S/C24H24N2O6/c1-15-12-23(30)32-20-14-17(10-11-18(15)20)25-24(31)19(13-16-6-3-2-4-7-16)26-21(27)8-5-9-22(28)29/h2-4,6-7,10-12,14,19H,5,8-9,13H2,1H3,(H,25,31)(H,26,27)(H,28,29)/t19-/m0/s1
• InChIKey: OTPFOMJAYSBYOD-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(1S)-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]-2-phenylethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: 4-{[(1S)-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]-2-phenylethyl]carbamoyl}butanoic acid
• Synonyms: Glut-Phe-AMC; N-Glutaryl-L-phenylalanine-4-methyl-7-coumarinylamide; Glutaryl-L-phenylalanine 7-amido-4-methylcoumarin

Database IDs

• CAS Number: 58632-47-6
• EC Number: 261-369-3
• MDL Number: MFCD00038083
• PubChem SID: 24873113; 24895269; 162226588
• PubChem CID: 13819625

CALCULATED PROPERTIES

• Acid pKa: 4.03676
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.235478
• LogD (pH = 7.4): -0.42791083
• Log P: 2.7097034
• Molar Refractivity: 118.1043 cm^3
• Polarizability: 44.818943 Å^3
• Polar Surface Area: 121.8 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +48.0±1°, c = 1% in methanol
• Fluorescence: λex 325 nm; λem 395 nm in H2O; λex 380 nm; λem 460 nm (Reaction product)

Safety Information

• German water hazard class: 3
• 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% (HPLC)
• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C24H24N2O6

DETAILS

Sigma Aldrich - 49737

Other Notes
Sensitive fluorogenic substrate for chymotrypsin1,2