(2S)-N-[(1S)-1-[({[(1S)-2-amino-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}methyl)(propan-2-yl)carbamoyl]ethyl]-2-{[(2S)-1-[2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetyl]pyrrolidin-2-yl]formamido}-4-methylpentanamide

• ChemBase ID: 106538
• Molecular Formular: C43H66N12O11
• Molecular Mass: 927.05794
• Monoisotopic Mass: 926.49740099
• SMILES: COc1ccc2c(c1)oc(=O)cc2CC(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N(CC(=O)N[C@@H](CN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)C(C)C
• Canonical SMILES: COc1ccc2c(c1)oc(=O)cc2CC(=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)CCCNC(=N)N)C)CN)C)CC(C)C
• InChI: InChI=1S/C43H66N12O11/c1-22(2)16-30(53-41(63)32-11-9-15-54(32)35(57)17-26-18-36(58)66-33-19-27(65-7)12-13-28(26)33)39(61)50-25(6)42(64)55(23(3)4)21-34(56)51-31(20-44)40(62)49-24(5)38(60)52-29(37(45)59)10-8-14-48-43(46)47/h12-13,18-19,22-25,29-32H,8-11,14-17,20-21,44H2,1-7H3,(H2,45,59)(H,49,62)(H,50,61)(H,51,56)(H,52,60)(H,53,63)(H4,46,47,48)/t24-,25-,29-,30-,31-,32-/m0/s1
• InChIKey: LMVMNUGKWWHJMV-YLOAKAIZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(1S)-1-[({[(1S)-2-amino-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}methyl)(propan-2-yl)carbamoyl]ethyl]-2-{[(2S)-1-[2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetyl]pyrrolidin-2-yl]formamido}-4-methylpentanamide
• IUPAC Traditional name: (2S)-N-[(1S)-1-[({[(1S)-2-amino-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}methyl)(isopropyl)carbamoyl]ethyl]-2-{[(2S)-1-[2-(7-methoxy-2-oxochromen-4-yl)acetyl]pyrrolidin-2-yl]formamido}-4-methylpentanamide
• Synonyms: 7-MCA-Pro-Leu-Ala-NVal-DPA-Ala-Arg-NH2; 7-MCA-PLA-NVal-DPA-A-R-NH2; 7-MCA-Pro-Leu-Ala-NVal-DPA-Ala-Arg-NH2

Database IDs

• PubChem SID: 162105967
• PubChem CID: 25108702

CALCULATED PROPERTIES

• Acid pKa: 11.5202055
• H Acceptors: 14
• H Donor: 10
• LogD (pH = 5.5): -8.494294
• LogD (pH = 7.4): -6.799916
• Log P: -4.428773
• Molar Refractivity: 249.0241 cm^3
• Polarizability: 92.702934 Å^3
• Polar Surface Area: 352.66 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MET07

A fluorogenic substrate for MMP-2 (gelatinase A; kcat/Km = 3.97 x 105 M^-1s^-1).
Excitation max.: ~325 nm, Emission max.: ~393 nm

REFERENCES

• Murphy, G. et al., J. Biol. Chem., 269:6632 (1994)