(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)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}butyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}butyl]carbamoyl}butanoic acid

• ChemBase ID: 133949
• Molecular Formular: C78H110N22O20
• Molecular Mass: 1675.8434
• Monoisotopic Mass: 1674.82667403
• SMILES: CCC[C@@H](C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])C(=O)N)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)Cc1cc(=O)oc2c1ccc(c2)OC
• 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)CCCCNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])CCCNC(=N)N)Cc1c[nH]c2c1cccc2)CCC)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/c1-5-16-53(68(106)95-58(37-45-42-88-50-18-7-6-17-48(45)50)71(109)92-54(21-12-33-86-77(81)82)69(107)90-52(67(80)105)19-9-11-32-85-51-28-25-46(99(115)116)40-61(51)100(117)118)91-70(108)55(29-30-64(102)103)93-74(112)66(43(2)3)96-73(111)60-24-15-36-98(60)76(114)57(20-8-10-31-79)94-72(110)59-23-14-35-97(59)75(113)56(22-13-34-87-78(83)84)89-63(101)38-44-39-65(104)120-62-41-47(119-4)26-27-49(44)62/h6-7,17-18,25-28,39-43,52-60,66,85,88H,5,8-16,19-24,29-38,79H2,1-4H3,(H2,80,105)(H,89,101)(H,90,107)(H,91,108)(H,92,109)(H,93,112)(H,94,110)(H,95,106)(H,96,111)(H,102,103)(H4,81,82,86)(H4,83,84,87)/t52-,53-,54-,55-,56-,57-,58-,59-,60-,66-/m0/s1
• InChIKey: TVZDWYYXHAIMCR-BKNSPTOHSA-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)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}butyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}butyl]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)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}butyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}butyl]carbamoyl}butanoic acid
• Synonyms: 7-Methoxycoumarin-4-acetyl-Arg-Pro-Lys-Pro-Val-Glu-Nva-Trp-Arg-(2,4-dinitrophenyl)Lys amide

Database IDs

• CAS Number: 158584-09-9
• MDL Number: MFCD00671420
• PubChem SID: 162228226
• PubChem CID: 16131108

CALCULATED PROPERTIES

• Acid pKa: -1.3110204
• H Acceptors: 27
• H Donor: 19
• LogD (pH = 5.5): -7.8939185
• LogD (pH = 7.4): -7.461445
• Log P: -3.267565
• Molar Refractivity: 455.8095 cm^3
• Polarizability: 167.20221 Å^3
• Polar Surface Area: 658.62 Å^2
• Rotatable Bonds: 49
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: mouse ... Nppa(230899)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - M9545

Amino Acid Sequence
MOCAc-Arg-Pro-Lys-Pro-Val-Glu-Nva-Trp-Arg-Lys-(DNP)-NH2
Application
Substrate for matrix metalloproteinases 3 and 9.