(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-{[(2S)-1-[(2S)-6-amino-2-{2-[(7-methoxy-2-oxo-2H-chromen-4-yl)formamido]acetamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-methylpentanamido]-4-methylpentanamido]-3-phenylpropanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-N-[(1R)-4-carbamimidamido-1-carbamoylbutyl]-6-[(2,4-dinitrophenyl)amino]hexanamide

• ChemBase ID: 106534
• Molecular Formular: C84H120N22O19
• Molecular Mass: 1741.9876
• Monoisotopic Mass: 1740.91000973
• SMILES: CC[C@H](C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)CNC(=O)c1cc(=O)oc2c1ccc(OC)c2)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])C(=O)N[C@H](CCCNC(=N)N)C(=O)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N)CCCNC(=N)N)CCCCNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])CC(C)C)CCCNC(=N)N)Cc1ccccc1)Cc1ccccc1)CC(C)C)[C@H](CC)C)NC(=O)CNC(=O)c1cc(=O)oc2c1ccc(c2)OC
• InChI: InChI=1S/C84H120N22O19/c1-8-50(6)71(103-80(117)66-30-21-39-104(66)82(119)61(27-15-17-35-85)95-69(107)47-94-73(110)56-46-70(108)125-68-45-54(124-7)32-33-55(56)68)81(118)102-63(41-49(4)5)77(114)100-65(43-52-24-13-10-14-25-52)79(116)101-64(42-51-22-11-9-12-23-51)78(115)98-60(29-20-38-93-84(89)90)75(112)99-62(40-48(2)3)76(113)97-59(74(111)96-58(72(86)109)28-19-37-92-83(87)88)26-16-18-36-91-57-34-31-53(105(120)121)44-67(57)106(122)123/h9-14,22-25,31-34,44-46,48-50,58-66,71,91H,8,15-21,26-30,35-43,47,85H2,1-7H3,(H2,86,109)(H,94,110)(H,95,107)(H,96,111)(H,97,113)(H,98,115)(H,99,112)(H,100,114)(H,101,116)(H,102,118)(H,103,117)(H4,87,88,92)(H4,89,90,93)/t50-,58+,59-,60-,61-,62-,63-,64-,65-,66-,71-/m0/s1
• InChIKey: OGCGNHYYHLIBAR-NFHABCNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-{[(2S)-1-[(2S)-6-amino-2-{2-[(7-methoxy-2-oxo-2H-chromen-4-yl)formamido]acetamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-methylpentanamido]-4-methylpentanamido]-3-phenylpropanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-N-[(1R)-4-carbamimidamido-1-carbamoylbutyl]-6-[(2,4-dinitrophenyl)amino]hexanamide
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-{[(2S)-1-[(2S)-6-amino-2-{2-[(7-methoxy-2-oxochromen-4-yl)formamido]acetamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-methylpentanamido]-4-methylpentanamido]-3-phenylpropanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-N-[(1R)-4-carbamimidamido-1-carbamoylbutyl]-6-[(2,4-dinitrophenyl)amino]hexanamide
• Synonyms: MCA-Gly-Lys-Pro-Ile-Leu-Phe-Phe-Arg-Leu-Lys(DNP)-D-Arg-NH2; MCA-GKPILFFRLL(DNP)DR-NH2; MCA-Gly-Lys-Pro-Ile-Leu-Phe-Phe-Arg-Leu-Lys(DNP)-D-Arg-NH2

Database IDs

• PubChem SID: 162105625
• PubChem CID: 25108698

CALCULATED PROPERTIES

• Acid pKa: 12.058455
• H Acceptors: 26
• H Donor: 19
• LogD (pH = 5.5): -6.072648
• LogD (pH = 7.4): -5.6432996
• Log P: 1.0967408
• Molar Refractivity: 481.94 cm^3
• Polarizability: 176.61325 Å^3
• Polar Surface Area: 643.42 Å^2
• Rotatable Bonds: 53
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MET011

An internally quenched fluorogenic 11-mer peptide that acts as a sensitive and selective substrate for cathepsins D and E (K_cat/K_m = 15.6 μM^-1s^-1 and 10.9 μM^-1s^-1 for rat gastric cathepsin D and human erythrocyte cathepsin E, respectively), but not cathepsins B, H, or L . Cleavage occurs between Phe-Phe residues and results in enhanced fluorescence. A useful tool for inhibitors screening or for the determination of cathepsins D and E activities in crude extracts of various tissues and cell lysates. MCA = (7-Methoxycoumarin-4-yl)acetyl
Excitation max.: ~328 nm, Emission max.: ~393 nm

REFERENCES

• Yasuda, Y et al., J. Biochem., 125:1137 (1999).