(4S)-4-[(2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2S)-5-carbamimidamido-2-[2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamido]pentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-methylbutanamido]-4-[({[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}butyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}methyl)(propan-2-yl)carbamoyl]butanoic acid

• ChemBase ID: 106536
• Molecular Formular: C78H110N22O20
• Molecular Mass: 1675.8434
• Monoisotopic Mass: 1674.82667403
• SMILES: COc1ccc2c(CC(=O)N[C@@H](CCCNC(=N)N)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N3CCC[C@H]3C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N(CC(=O)N[C@@H](Cc3c[nH]c4c3cccc4)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCNc3ccc(cc3[N+](=O)[O-])[N+](=O)[O-])C(=O)N)C(C)C)cc(=O)oc2c1
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N(C(C)C)CC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCCCNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])CCCNC(=N)N)Cc1c[nH]c2c1cccc2)CCC(=O)O)C(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)Cc1cc(=O)oc2c1ccc(c2)OC)CCCNC(=N)N
• InChI: InChI=1S/C78H110N22O20/c1-43(2)67(95-72(110)60-23-15-35-97(60)75(113)56(19-8-10-30-79)93-71(109)59-22-14-34-96(59)74(112)55(21-13-33-87-78(83)84)89-63(101)37-45-38-66(105)120-62-40-48(119-5)25-26-50(45)62)73(111)94-57(28-29-65(103)104)76(114)98(44(3)4)42-64(102)90-58(36-46-41-88-51-17-7-6-16-49(46)51)70(108)92-54(20-12-32-86-77(81)82)69(107)91-53(68(80)106)18-9-11-31-85-52-27-24-47(99(115)116)39-61(52)100(117)118/h6-7,16-17,24-27,38-41,43-44,53-60,67,85,88H,8-15,18-23,28-37,42,79H2,1-5H3,(H2,80,106)(H,89,101)(H,90,102)(H,91,107)(H,92,108)(H,93,109)(H,94,111)(H,95,110)(H,103,104)(H4,81,82,86)(H4,83,84,87)/t53-,54-,55-,56-,57-,58-,59-,60-,67-/m0/s1
• InChIKey: NHVIPHCPJRQKQM-HLHYCTPMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2S)-5-carbamimidamido-2-[2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamido]pentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-methylbutanamido]-4-[({[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}butyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}methyl)(propan-2-yl)carbamoyl]butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2S)-5-carbamimidamido-2-[2-(7-methoxy-2-oxochromen-4-yl)acetamido]pentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-methylbutanamido]-4-[({[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}butyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}methyl)(isopropyl)carbamoyl]butanoic acid
• Synonyms: 7-MCA-Arg-Pro-Lys-Pro-Val-Glu-NVal-Trp-Arg-Lys(DNP)-NH2; 7-MCA-RPKPVE-NVal-WRL(DNP)-NH2; 7-MCA-Arg-Pro-Lys-Pro-Val-Glu-NVal-Trp-Arg-Lys(DNP)-NH2

Database IDs

• PubChem SID: 162105713
• PubChem CID: 25108700

CALCULATED PROPERTIES

• Acid pKa: -1.3110194
• H Acceptors: 27
• H Donor: 18
• LogD (pH = 5.5): -8.434603
• LogD (pH = 7.4): -8.000263
• Log P: -3.8059318
• Molar Refractivity: 456.2547 cm^3
• Polarizability: 167.20221 Å^3
• Polar Surface Area: 649.83 Å^2
• Rotatable Bonds: 48
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MET05

A fluorogenic substrate for MMP-2 and 9.

REFERENCES

• Nagase, M. et al., J. Biol. Chem., 269:20952 (1994).