(2S)-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}butyl]carbamoyl}-2-[(2,4-dinitrophenyl)amino]ethyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]-2-[(2S)-2-[(2S)-2-{[(2S)-1-[2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]propanamido]pentanediamide

• ChemBase ID: 106677
• Molecular Formular: C69H103N23O24
• Molecular Mass: 1638.69582
• Monoisotopic Mass: 1637.75463129
• SMILES: COc1ccc2c(CC(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CNc3ccc(cc3[N+](=O)[O-])[N+](=O)[O-])C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)cc(=O)oc2c1
• 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@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[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCCNC(=N)N)CO)CO)CO)CCCNC(=N)N)CNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])C(C)C)C)CCC(=O)N)C)CC(C)C
• InChI: InChI=1S/C69H103N23O24/c1-32(2)23-44(84-66(109)49-13-10-22-90(49)53(97)24-36-25-54(98)116-51-27-38(115-7)15-16-39(36)51)61(104)80-34(5)57(100)82-43(18-19-52(70)96)59(102)79-35(6)58(101)89-55(33(3)4)67(110)85-45(28-78-40-17-14-37(91(111)112)26-50(40)92(113)114)62(105)83-42(12-9-21-77-69(74)75)60(103)86-47(30-94)64(107)88-48(31-95)65(108)87-46(29-93)63(106)81-41(56(71)99)11-8-20-76-68(72)73/h14-17,25-27,32-35,41-49,55,78,93-95H,8-13,18-24,28-31H2,1-7H3,(H2,70,96)(H2,71,99)(H,79,102)(H,80,104)(H,81,106)(H,82,100)(H,83,105)(H,84,109)(H,85,110)(H,86,103)(H,87,108)(H,88,107)(H,89,101)(H4,72,73,76)(H4,74,75,77)/t34-,35-,41-,42-,43-,44-,45-,46-,47-,48-,49-,55-/m0/s1
• InChIKey: QWPFCDHLHMOCKZ-ZZLDSPSDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}butyl]carbamoyl}-2-[(2,4-dinitrophenyl)amino]ethyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]-2-[(2S)-2-[(2S)-2-{[(2S)-1-[2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]propanamido]pentanediamide
• IUPAC Traditional name: (2S)-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}butyl]carbamoyl}-2-[(2,4-dinitrophenyl)amino]ethyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]-2-[(2S)-2-[(2S)-2-{[(2S)-1-[2-(7-methoxy-2-oxochromen-4-yl)acetyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]propanamido]pentanediamide
• Synonyms: MCA-Pro-Leu-Ala-Gln-Ala-Val-Dap(DNP)-Arg-Ser-Ser-Ser-Arg-NH2; MCA-PLAQAV-Dap(DNP)-RSSSR-NH2; MCA-Pro-Leu-Ala-Gln-Ala-Val-Dap(DNP)-Arg-Ser-Ser-Ser-Arg-NH₂

Database IDs

• PubChem SID: 162105614
• PubChem CID: 25108821

CALCULATED PROPERTIES

• Acid pKa: 10.957828
• H Acceptors: 30
• H Donor: 23
• LogD (pH = 5.5): -13.2858
• LogD (pH = 7.4): -13.266179
• Log P: -9.56174
• Molar Refractivity: 426.5884 cm^3
• Polarizability: 155.22754 Å^3
• Polar Surface Area: 750.28 Å^2
• Rotatable Bonds: 48
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03TNF160

A fluorogenic substrate for TNF(α) converting enzyme (TACE)

REFERENCES

• Van, D.E. et al., Bioorg. Med. Chem. Lett., 7:1219 (1997).