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

• ChemBase ID: 155097
• Molecular Formular: C37H42F3N5O13
• Molecular Mass: 821.7502896
• Monoisotopic Mass: 821.27312109
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(cc(=O)oc2c1)C(F)(F)F)NC(=O)OCc1ccccc1
• Canonical SMILES: CC[C@@H]([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)[C@H](O)C)CCC(=O)O)NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C37H42F3N5O13/c1-4-18(2)30(45-36(56)57-17-20-8-6-5-7-9-20)34(54)42-24(12-13-27(47)48)32(52)44-31(19(3)46)35(55)43-25(16-28(49)50)33(53)41-21-10-11-22-23(37(38,39)40)15-29(51)58-26(22)14-21/h5-11,14-15,18-19,24-25,30-31,46H,4,12-13,16-17H2,1-3H3,(H,41,53)(H,42,54)(H,43,55)(H,44,52)(H,45,56)(H,47,48)(H,49,50)/t18-,19+,24-,25-,30-,31-/m0/s1
• InChIKey: RCIFCAJYIPUCJW-QXPVPWKFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-methylpentanamido]-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-methylpentanamido]-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}butanoic acid
• Synonyms: Cbz-IETD-AFC; Z-Ile-Glu-Thr-Asp 7-amido-4-trifluoromethylcoumarin

Database IDs

• CAS Number: 219138-02-0
• MDL Number: MFCD01318832
• PubChem SID: 162249235
• PubChem CID: 71312079

CALCULATED PROPERTIES

• Acid pKa: 3.5087132
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -1.7349485
• LogD (pH = 7.4): -4.8798695
• Log P: 1.5893463
• Molar Refractivity: 193.4368 cm^3
• Polarizability: 73.90862 Å^3
• Polar Surface Area: 275.86 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

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 ... CARD8(22900), CASP8(841), CASP8AP2(9994), CFLAR(8837), GZMB(3002)mouse ... CFLAR(117279), GZMB(171528)rat ... CASP8(12370), CFLAR(12633), GZMB(14939), RGD1561819(502004), RGD1562700(502007)

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C37H42F3N5O13

DETAILS

Sigma Aldrich - C5599

Amino Acid Sequence
Z-Ile-Glu-Thr-Asp-AFC
Application
Fluorogenic substrate for caspase 8 and granzyme B.
Biochem/physiol Actions
IETD is the sequence of amino acid residues 172-175 of procaspase 3, which is cleaved during apoptosis to produce the p12 subunit and a p20 peptide that is further cleaved to form the p17 subunit of mature caspase 3.