(2S)-N-[(2S)-6-amino-1-[(2S)-2-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}methyl)(propan-2-yl)carbamoyl]ethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]-1-[(2S)-5-carbamimidamido-2-[2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamido]pentanoyl]pyrrolidine-2-carboxamide

• ChemBase ID: 106539
• Molecular Formular: C79H105N19O19S
• Molecular Mass: 1656.8599
• Monoisotopic Mass: 1655.75548324
• 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](Cc3ccc(O)cc3)C(=O)N[C@@H](C)C(=O)N(CC(=O)N[C@@H](Cc3c[nH]c4c3cccc4)C(=O)N[C@@H](CCSC)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-])CCSC)Cc1c[nH]c2c1cccc2)C)Cc1ccc(cc1)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)Cc1cc(=O)oc2c1ccc(c2)OC)CCCNC(=N)N
• InChI: InChI=1S/C79H105N19O19S/c1-45(2)96(44-68(101)89-62(38-49-43-86-55-16-7-6-15-53(49)55)73(106)91-58(30-36-118-5)71(104)90-57(70(81)103)17-9-11-32-84-56-29-24-50(97(112)113)41-65(56)98(114)115)76(109)46(3)87-72(105)61(37-47-22-25-51(99)26-23-47)93-75(108)64-21-14-35-95(64)78(111)60(18-8-10-31-80)92-74(107)63-20-13-34-94(63)77(110)59(19-12-33-85-79(82)83)88-67(100)39-48-40-69(102)117-66-42-52(116-4)27-28-54(48)66/h6-7,15-16,22-29,40-43,45-46,57-64,84,86,99H,8-14,17-21,30-39,44,80H2,1-5H3,(H2,81,103)(H,87,105)(H,88,100)(H,89,101)(H,90,104)(H,91,106)(H,92,107)(H,93,108)(H4,82,83,85)/t46-,57-,58-,59-,60-,61-,62-,63-,64-/m0/s1
• InChIKey: BFPNRIFGVHTQLD-IYZXMFFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(2S)-6-amino-1-[(2S)-2-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}methyl)(propan-2-yl)carbamoyl]ethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]-1-[(2S)-5-carbamimidamido-2-[2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamido]pentanoyl]pyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S)-N-[(2S)-6-amino-1-[(2S)-2-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}methyl)(isopropyl)carbamoyl]ethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]-1-[(2S)-5-carbamimidamido-2-[2-(7-methoxy-2-oxochromen-4-yl)acetamido]pentanoyl]pyrrolidine-2-carboxamide
• Synonyms: 7-MCA-Arg-Pro-Lys-Pro-Tyr-Ala-NVal-Trp-Met-Lys (DNP)-NH2; 7-MCA-RPKPYA-NVal-WML(DNP)-NH2; 7-MCA-Arg-Pro-Lys-Pro-Tyr-Ala-NVal-Trp-Met-Lys (DNP)-NH2

Database IDs

• PubChem SID: 162105516
• PubChem CID: 25108703

CALCULATED PROPERTIES

• Acid pKa: 9.420387
• H Acceptors: 23
• H Donor: 15
• LogD (pH = 5.5): -4.396849
• LogD (pH = 7.4): -3.699739
• Log P: 0.47624987
• Molar Refractivity: 446.7315 cm^3
• Polarizability: 167.6143 Å^3
• Polar Surface Area: 570.86 Å^2
• Rotatable Bonds: 45
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MET08

A fluorogenic substrate for MMP-1, 2, 3 and 9.

REFERENCES

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