(4S)-4-{[(1S)-3-carboxy-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}propyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid

• ChemBase ID: 106361
• Molecular Formular: C32H38F3N5O13
• Molecular Mass: 757.6650296
• Monoisotopic Mass: 757.24182096
• SMILES: CC(C)C[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CC(=O)O)CCC(=O)O)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C32H38F3N5O13/c1-14(2)10-21(36-15(3)41)31(52)39-19(6-8-24(42)43)28(49)38-20(7-9-25(44)45)29(50)40-22(13-26(46)47)30(51)37-16-4-5-17-18(32(33,34)35)12-27(48)53-23(17)11-16/h4-5,11-12,14,19-22H,6-10,13H2,1-3H3,(H,36,41)(H,37,51)(H,38,49)(H,39,52)(H,40,50)(H,42,43)(H,44,45)(H,46,47)/t19-,20-,21-,22-/m0/s1
• InChIKey: ZPNCQMJLTSFJQH-CMOCDZPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-3-carboxy-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}propyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-3-carboxy-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}propyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: Ac-Leu-Glu-Glu-Asp-AFC; Ac-LEED-AFC; Ac-Leu-Glu-Glu-Asp-7-Amino-4-trifluoromethylcoumarin; N-Acetyl-Leu-Glu-Glu-Asp-7-amido-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD03452816
• PubChem SID: 162087296
• PubChem CID: 25108580

CALCULATED PROPERTIES

• Acid pKa: 3.2887821
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -5.5887065
• LogD (pH = 7.4): -10.266377
• Log P: -0.55518746
• Molar Refractivity: 172.1055 cm^3
• Polarizability: 65.57008 Å^3
• Polar Surface Area: 283.7 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO/DMF: soluble20 mM
• Apperance: powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)

DETAILS

MP Biomedicals - 03AFC158

A fluorogenic substrate for Caspase-13.

Sigma Aldrich - A5720

Substrates
Fluorogenic substrate for caspase 13.

REFERENCES

• Humke, E.W. et al., J. Biol. Chem., 273(25):15702 (1998).