(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-{[(2S)-1-(2,4-dinitrophenyl)pyrrolidin-2-yl]formamido}-4-methylpentanamido]acetamido}-4-(methylsulfanyl)butanamido]-3-(1H-indol-3-yl)propanamido]-3-hydroxypropanamido]pentanoic acid

• ChemBase ID: 106535
• Molecular Formular: C44H61N13O13S
• Molecular Mass: 1012.09944
• Monoisotopic Mass: 1011.42325008
• SMILES: CSCC[C@H](NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@@H]1CCCN1c1ccc([N+](=O)[O-])cc1[N+](=O)[O-])C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O
• Canonical SMILES: CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)CO)Cc1c[nH]c2c1cccc2)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H]1CCCN1c1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])CC(C)C
• InChI: InChI=1S/C44H61N13O13S/c1-24(2)18-31(53-42(64)35-11-7-16-55(35)34-13-12-26(56(67)68)20-36(34)57(69)70)38(60)49-22-37(59)50-29(14-17-71-3)39(61)52-32(19-25-21-48-28-9-5-4-8-27(25)28)40(62)54-33(23-58)41(63)51-30(43(65)66)10-6-15-47-44(45)46/h4-5,8-9,12-13,20-21,24,29-33,35,48,58H,6-7,10-11,14-19,22-23H2,1-3H3,(H,49,60)(H,50,59)(H,51,63)(H,52,61)(H,53,64)(H,54,62)(H,65,66)(H4,45,46,47)/t29-,30-,31-,32-,33-,35-/m0/s1
• InChIKey: AZDJGXPMCRXEQN-SUUSVYONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-{[(2S)-1-(2,4-dinitrophenyl)pyrrolidin-2-yl]formamido}-4-methylpentanamido]acetamido}-4-(methylsulfanyl)butanamido]-3-(1H-indol-3-yl)propanamido]-3-hydroxypropanamido]pentanoic acid
• IUPAC Traditional name: (2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-{[(2S)-1-(2,4-dinitrophenyl)pyrrolidin-2-yl]formamido}-4-methylpentanamido]acetamido}-4-(methylsulfanyl)butanamido]-3-(1H-indol-3-yl)propanamido]-3-hydroxypropanamido]pentanoic acid
• Synonyms: 2-4-DNP-PLGMWSR; 2-4-DNP-Pro-Leu-Gly-Met-Trp-Ser-Arg; 2-4-DNP-Pro-Leu-Gly-Met-Trp-Ser-Arg

Database IDs

• PubChem SID: 162105514
• PubChem CID: 25108699

CALCULATED PROPERTIES

• Acid pKa: 3.4373934
• H Acceptors: 17
• H Donor: 12
• LogD (pH = 5.5): -1.6754396
• LogD (pH = 7.4): -1.6724211
• Log P: -1.6724509
• Molar Refractivity: 269.2347 cm^3
• Polarizability: 99.25326 Å^3
• Polar Surface Area: 404.7 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MET04

A fluorogenic substrate for MMP-2 and 9.

REFERENCES

• Netzel-Amett, S. et al., Anal. Biochem., 195:86 (1991).