(4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-acetamidopropanamido]butanoic acid

• ChemBase ID: 106355
• Molecular Formular: C29H34F3N5O11
• Molecular Mass: 685.6023696
• Monoisotopic Mass: 685.22069159
• SMILES: CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)C)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: OC(=O)C[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)C)CCC(=O)O
• InChI: InChI=1S/C29H34F3N5O11/c1-12(2)24(37-26(45)18(7-8-21(39)40)35-25(44)13(3)33-14(4)38)28(47)36-19(11-22(41)42)27(46)34-15-5-6-16-17(29(30,31)32)10-23(43)48-20(16)9-15/h5-6,9-10,12-13,18-19,24H,7-8,11H2,1-4H3,(H,33,38)(H,34,46)(H,35,44)(H,36,47)(H,37,45)(H,39,40)(H,41,42)/t13-,18-,19-,24-/m0/s1
• InChIKey: OGDZWRZGOFQIOD-MNOOHBRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-acetamidopropanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-acetamidopropanamido]butanoic acid
• Synonyms: Ac-Ala-Glu-Val-Asp-AFC; Ac-AEVDAFC; Ac-Ala-Glu-Val-Asp-7-Amino-4-trifluoromethylcoumarin; Ac-AEVD-AFC; N-Acetyl-Ala-Glu-Val-Asp-7-amido-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD03452804
• PubChem SID: 162105959
• PubChem CID: 25108574

CALCULATED PROPERTIES

• Acid pKa: 3.6263585
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -3.6602817
• LogD (pH = 7.4): -6.910787
• Log P: -0.5686517
• Molar Refractivity: 156.6371 cm^3
• Polarizability: 59.430145 Å^3
• Polar Surface Area: 246.4 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

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

Pharmacology Properties

• Gene Information: human ... CASP8(841)mouse ... CASP8(12370)rat ... CASP8(64044)

Product Information

• Purity: >96% (HPLC)
• Empirical Formula (Hill Notation): C29H34N5O11F3

DETAILS

MP Biomedicals - 03AFC145

A fluorogenic substrate for Caspase-6 and Caspase-8.

Sigma Aldrich - A0973

Application
Fluorogenic substrate for caspase 8 and 9.

REFERENCES

• Garcia-Calvo, M. et al., J. Biol. Chem., 273(49):32608 (1998).