(3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-[(2S)-2-acetamido-3-methylbutanamido]propanoic acid

• ChemBase ID: 106353
• Molecular Formular: C33H41F3N6O12
• Molecular Mass: 770.7068496
• Monoisotopic Mass: 770.27345544
• SMILES: CC(C)[C@H](NC(=O)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](C(C)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](NC(=O)[C@H](C(C)C)NC(=O)C)CC(=O)O)C
• InChI: InChI=1S/C33H41F3N6O12/c1-13(2)26(38-16(6)43)32(53)41-21(12-24(46)47)30(51)42-27(14(3)4)31(52)37-15(5)28(49)40-20(11-23(44)45)29(50)39-17-7-8-18-19(33(34,35)36)10-25(48)54-22(18)9-17/h7-10,13-15,20-21,26-27H,11-12H2,1-6H3,(H,37,52)(H,38,43)(H,39,50)(H,40,49)(H,41,53)(H,42,51)(H,44,45)(H,46,47)/t15-,20-,21-,26-,27-/m0/s1
• InChIKey: BKQMJQIAIFEZJR-OIOUIRQFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-[(2S)-2-acetamido-3-methylbutanamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-[(2S)-2-acetamido-3-methylbutanamido]propanoic acid
• Synonyms: N-Acetyl-Val-Asp-Val-Ala-Asp-7-amido-4-trifluoromethylcoumarin; Ac-Val-Asp-Val-Ala-Asp-AFC; Ac-VDVAD-AFC; Ac-Val-Asp-Val-Ala-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD04037014
• PubChem SID: 162089019
• PubChem CID: 25108572

CALCULATED PROPERTIES

• Acid pKa: 3.5692508
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -3.5804107
• LogD (pH = 7.4): -6.8006287
• Log P: -0.5063367
• Molar Refractivity: 178.1751 cm^3
• Polarizability: 68.00339 Å^3
• Polar Surface Area: 275.5 Å^2
• Rotatable Bonds: 18
• 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

Pharmacology Properties

• Gene Information: human ... CASP2(835)mouse ... CASP2(12366)rat ... CASP2(64314)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 03AFC142

A fluorogenic substrate for Caspase-2.

Sigma Aldrich - A5345

Amino Acid Sequence
NAc-Val-Asp-Val-Ala-Asp-AFC
Substrates
Fluorogenic substrate for caspase 2.

REFERENCES

• Thornberry, N.A. and Lazebnik, Y., Science, 281:1312 (1998).