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

• ChemBase ID: 106343
• Molecular Formular: C33H36F3N5O10
• Molecular Mass: 719.6616496
• Monoisotopic Mass: 719.24142704
• SMILES: CC(C)[C@H](NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)C)C(=O)N[C@@H](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](NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)C)C
• InChI: InChI=1S/C33H36F3N5O10/c1-15(2)28(41-31(49)23(38-17(4)42)11-18-5-8-20(43)9-6-18)32(50)37-16(3)29(47)40-24(14-26(44)45)30(48)39-19-7-10-21-22(33(34,35)36)13-27(46)51-25(21)12-19/h5-10,12-13,15-16,23-24,28,43H,11,14H2,1-4H3,(H,37,50)(H,38,42)(H,39,48)(H,40,47)(H,41,49)(H,44,45)/t16-,23-,24-,28-/m0/s1
• InChIKey: GWKJISJKNKIJNP-DEQDFGQZSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• MDL Number: MFCD01318881
• PubChem SID: 162087292
• PubChem CID: 16760708

CALCULATED PROPERTIES

• Acid pKa: 3.6620743
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -0.6982235
• LogD (pH = 7.4): -2.1865206
• Log P: 1.1372601
• Molar Refractivity: 172.4466 cm^3
• Polarizability: 65.18709 Å^3
• Polar Surface Area: 229.33 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white 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

Pharmacology Properties

• Gene Information: human ... CASP1(834), CASP4(837)mouse ... CASP1(12362), CASP4(12363)rat ... CASP1(25166), CASP4(114555)

Product Information

• Purity: ≥95% (HPLC)

DETAILS

MP Biomedicals - 03AFC120

A fluorogenic substrate for Caspase-1 (ICE). May also be used as a caspase-3, caspase-4, or caspase-7 substrate. Reaction can be monitored by a blue to green shift in fluorescence upon cleavage of the AFC fluorophore.

Sigma Aldrich - A9965

Amino Acid Sequence
NAc-Tyr-Val-Ala-Asp-AFC
Substrates
Membrane-permeable fluorogenic substrate for caspase 1 (ICE) and caspase 4 (TX).

REFERENCES

• Marcelli, M. et al., Cancer Res., 58:76 (1998).
• Susin, S.A., et al. 1999. J. Exp. Med. 189, 381.
• Thornberry, N.A. and Lazebnik, Y. 1998. Science 281, 1312.