(4S)-4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]-4-{[(1S,2S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid

• ChemBase ID: 134108
• Molecular Formular: C38H44F3N5O12
• Molecular Mass: 819.7774696
• Monoisotopic Mass: 819.29385653
• SMILES: CC[C@H](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](CCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CC(=O)O)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1)CCC(=O)O)C
• InChI: InChI=1S/C38H44F3N5O12/c1-5-20(4)32(36(55)44-26(17-29(49)50)34(53)42-22-11-12-23-24(38(39,40)41)16-30(51)58-27(23)15-22)45-33(52)25(13-14-28(47)48)43-35(54)31(19(2)3)46-37(56)57-18-21-9-7-6-8-10-21/h6-12,15-16,19-20,25-26,31-32H,5,13-14,17-18H2,1-4H3,(H,42,53)(H,43,54)(H,44,55)(H,45,52)(H,46,56)(H,47,48)(H,49,50)/t20-,25-,26-,31-,32-/m0/s1
• InChIKey: OEVAAZFKVRJQQH-UXAYAQJLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]-4-{[(1S,2S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]-4-{[(1S,2S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid
• Synonyms: Ac-VEID-AFC; N-Acetyl-Val-Glu-Ile-Asp-7-amido-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD01318833
• PubChem SID: 162228385
• PubChem CID: 71308761

CALCULATED PROPERTIES

• Acid pKa: 3.6600442
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 0.057531007
• LogD (pH = 7.4): -3.2169778
• Log P: 3.1071765
• Molar Refractivity: 196.4699 cm^3
• Polarizability: 75.02723 Å^3
• Polar Surface Area: 255.63 Å^2
• Rotatable Bonds: 21
• 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 ... CASP6(839)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - A5095

Amino Acid Sequence
NAc-Val-Glu-Ile-Asp-AFC
Biochem/physiol Actions
Fluorogenic substrate for caspase 6 (Mch-2α).