(3S)-3-[(2S)-2-[(2S)-2-acetamido-3-methylbutanamido]propanamido]-3-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}propanoic acid

• ChemBase ID: 153579
• Molecular Formular: C24H27F3N4O8
• Molecular Mass: 556.4883896
• Monoisotopic Mass: 556.1780985
• SMILES: C[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(cc(=O)oc2c1)C(F)(F)F)NC(=O)[C@H](C(C)C)NC(=O)C
• Canonical SMILES: OC(=O)C[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)C)C
• InChI: InChI=1S/C24H27F3N4O8/c1-10(2)20(29-12(4)32)23(38)28-11(3)21(36)31-16(9-18(33)34)22(37)30-13-5-6-14-15(24(25,26)27)8-19(35)39-17(14)7-13/h5-8,10-11,16,20H,9H2,1-4H3,(H,28,38)(H,29,32)(H,30,37)(H,31,36)(H,33,34)/t11-,16-,20-/m0/s1
• InChIKey: SUKBHHDBYOSKMD-QUGJLEDBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-acetamido-3-methylbutanamido]propanamido]-3-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-acetamido-3-methylbutanamido]propanamido]-3-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}propanoic acid
• Synonyms: Ac-VAD-AFC; N-Acetyl-Val-Ala-Asp-7-amido-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD02259218
• PubChem SID: 162247718
• PubChem CID: 71311681

CALCULATED PROPERTIES

• Acid pKa: 3.6620889
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.5144229
• LogD (pH = 7.4): -2.9993737
• Log P: 0.321018
• Molar Refractivity: 128.5493 cm^3
• Polarizability: 48.32918 Å^3
• Polar Surface Area: 180.0 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• German water hazard class: 3
• Safety Statements: 22-24/25
• Storage Temperature: -20°C

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C24H27F3N4O8

DETAILS

Sigma Aldrich - A0723

Substrates
General class of fluorogenic caspase substrates.