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

• ChemBase ID: 106328
• Molecular Formular: C40H50F3N5O10
• Molecular Mass: 817.8477096
• Monoisotopic Mass: 817.35097749
• SMILES: CC(C)C[C@H](NC(=O)CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)Cc1ccc(cc1)O)C(C)C)NC(=O)[C@@H](NC(=O)CCC(=O)O)CC(C)C)C
• InChI: InChI=1S/C40H50F3N5O10/c1-20(2)15-28(45-32(50)13-14-33(51)52)37(55)46-29(16-21(3)4)38(56)48-35(22(5)6)39(57)47-30(17-23-7-10-25(49)11-8-23)36(54)44-24-9-12-26-27(40(41,42)43)19-34(53)58-31(26)18-24/h7-12,18-22,28-30,35,49H,13-17H2,1-6H3,(H,44,54)(H,45,50)(H,46,55)(H,47,57)(H,48,56)(H,51,52)/t28-,29-,30-,35-/m0/s1
• InChIKey: ZSJPCNKJLSJEQF-DWNBPJMTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-(4-hydroxyphenyl)-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-(4-hydroxyphenyl)-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}propanoic acid
• Synonyms: Suc-Leu-Leu-Val-Tyr-AFC; Suc-LLVY-AFC; Suc-Leu-Leu-Val-Tyr-7-Amino-4-trifluoromethylcoumarin; N-Succinyl-Leu-Leu-Val-Tyr-7-amido-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD03453017
• PubChem SID: 162105397
• PubChem CID: 25108548

CALCULATED PROPERTIES

• Acid pKa: 4.326521
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): 2.912352
• LogD (pH = 7.4): 1.1652161
• Log P: 4.112155
• Molar Refractivity: 204.6517 cm^3
• Polarizability: 77.91597 Å^3
• Polar Surface Area: 229.33 Å^2
• Rotatable Bonds: 20
• 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

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C40H50N5O10F3

DETAILS

MP Biomedicals - 03AFC086

A fluorogenic substrate for Chymotrypsin.

Sigma Aldrich - S4939

Biochem/physiol Actions
Chymotrypsin and multicatalytic endopeptidase complex: proteasome substrate similar to AMC derivative

REFERENCES

• Ishiwra, S. et al., FEBS Lett., 189:119 (1988).
• Tsukahara, T. et al., Eur. J. Biochem., 177:261 (1988).