(2S)-6-amino-N-[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butyl]-2-[(2S,3R)-2-[(2S)-5-carbamimidamido-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}pentanamido]-3-hydroxybutanamido]hexanamide; trifluoroacetic acid

• ChemBase ID: 154628
• Molecular Formular: C39H58F3N13O11
• Molecular Mass: 941.9535296
• Monoisotopic Mass: 941.4330844
• SMILES: Cc1cc(=O)oc2c1ccc(c2)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCC(=O)N1.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.NCCCC[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)CCCNC(=N)N)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H]1CCC(=O)N1)CCCNC(=N)N
• InChI: InChI=1S/C37H57N13O9.C2HF3O2/c1-19-17-29(53)59-27-18-21(10-11-22(19)27)45-31(54)24(8-5-15-43-36(39)40)47-32(55)23(7-3-4-14-38)49-35(58)30(20(2)51)50-34(57)25(9-6-16-44-37(41)42)48-33(56)26-12-13-28(52)46-26;3-2(4,5)1(6)7/h10-11,17-18,20,23-26,30,51H,3-9,12-16,38H2,1-2H3,(H,45,54)(H,46,52)(H,47,55)(H,48,56)(H,49,58)(H,50,57)(H4,39,40,43)(H4,41,42,44);(H,6,7)/t20-,23+,24+,25+,26+,30+;/m1./s1
• InChIKey: BHPUHMHLXQHSPN-HUQKKSBQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-N-[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butyl]-2-[(2S,3R)-2-[(2S)-5-carbamimidamido-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}pentanamido]-3-hydroxybutanamido]hexanamide; trifluoroacetic acid
• IUPAC Traditional name: (2S)-6-amino-N-[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]butyl]-2-[(2S,3R)-2-[(2S)-5-carbamimidamido-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}pentanamido]-3-hydroxybutanamido]hexanamide; trifluoroacetic acid
• Synonyms: L-Pyroglutamyl-Arg-Thr-Lys-Arg-7-amido-4-methylcoumarin trifluoroacetate salt; Pyr-Arg-Thr-Lys-Arg-7-amido-4-methylcoumarin trifluoroacetate salt; pGlu-Arg-Thr-Lys-Arg-7-amido-4-methylcoumarin trifluoroacetate salt

Database IDs

• MDL Number: MFCD17215945
• PubChem SID: 162248766
• PubChem CID: 71311915

CALCULATED PROPERTIES

• Acid pKa: 11.041909
• H Acceptors: 15
• H Donor: 14
• LogD (pH = 5.5): -11.929311
• LogD (pH = 7.4): -11.490799
• Log P: -4.883376
• Molar Refractivity: 235.4536 cm^3
• Polarizability: 82.162766 Å^3
• Polar Surface Area: 370.95 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥96% (HPLC)
• Empirical Formula (Hill Notation): C37H57N13O9 · xC2HF3O2

DETAILS

Sigma Aldrich - 30916

Application
pGlu-Arg-Thr-Lys-Arg-7-amido-4-methylcoumarin was used as a substrate for the proprotein convertase PC1/3 and activity was measured by the fluorescence generated by the release of amino-4-methylcoumarin. 1