(4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}butyl]carbamoyl}-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}butyl]carbamoyl}-2-phenylethyl]carbamoyl}-3-carboxypropyl]carbamoyl}ethyl]carbamoyl}-2-carboxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-hydroxy-2-[2-(4-methoxy-2-oxo-2H-chromen-8-yl)acetamido]propanamido]butanoic acid

• ChemBase ID: 106462
• Molecular Formular: C86H125N27O29
• Molecular Mass: 2001.0762
• Monoisotopic Mass: 1999.91365112
• SMILES: COc1cc(=O)oc2c1cccc2CC(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N
• Canonical SMILES: OC[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[C@H](C(=O)N[C@H](C(=O)N)CCCNC(=N)N)CCCNC(=N)N)CCCCNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])CCCNC(=N)N)Cc1ccccc1)CCC(=O)O)C)CC(=O)O)CC(C)C)CC(=O)N)C(C)C)CCC(=O)O)NC(=O)Cc1cccc2c1oc(=O)cc2OC
• InChI: InChI=1S/C86H125N27O29/c1-42(2)34-56(107-81(134)58(38-63(87)115)110-83(136)69(43(3)4)111-77(130)55(27-29-66(119)120)106-82(135)60(41-114)100-64(116)36-46-18-12-19-48-62(141-6)40-68(123)142-70(46)48)79(132)109-59(39-67(121)122)78(131)99-44(5)72(125)102-54(26-28-65(117)118)76(129)108-57(35-45-16-8-7-9-17-45)80(133)105-53(23-15-33-98-86(93)94)75(128)103-51(20-10-11-30-95-49-25-24-47(112(137)138)37-61(49)113(139)140)74(127)104-52(22-14-32-97-85(91)92)73(126)101-50(71(88)124)21-13-31-96-84(89)90/h7-9,12,16-19,24-25,37,40,42-44,50-60,69,95,114H,10-11,13-15,20-23,26-36,38-39,41H2,1-6H3,(H2,87,115)(H2,88,124)(H,99,131)(H,100,116)(H,101,126)(H,102,125)(H,103,128)(H,104,127)(H,105,133)(H,106,135)(H,107,134)(H,108,129)(H,109,132)(H,110,136)(H,111,130)(H,117,118)(H,119,120)(H,121,122)(H4,89,90,96)(H4,91,92,97)(H4,93,94,98)/t44-,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,69-/m0/s1
• InChIKey: HQBVBLTXSUAYNN-QQBFYWPQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}butyl]carbamoyl}-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}butyl]carbamoyl}-2-phenylethyl]carbamoyl}-3-carboxypropyl]carbamoyl}ethyl]carbamoyl}-2-carboxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-hydroxy-2-[2-(4-methoxy-2-oxo-2H-chromen-8-yl)acetamido]propanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}butyl]carbamoyl}-5-[(2,4-dinitrophenyl)amino]pentyl]carbamoyl}butyl]carbamoyl}-2-phenylethyl]carbamoyl}-3-carboxypropyl]carbamoyl}ethyl]carbamoyl}-2-carboxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-hydroxy-2-[2-(4-methoxy-2-oxochromen-8-yl)acetamido]propanamido]butanoic acid
• Synonyms: MCA-Ser-Glu-Val-Asn-Leu-Asp-Ala-Glu-Phe-Arg-Lys(DNP)-Arg-Arg-NH2; MCA-SEVALDAEFRL(DNP)RR-NH2; MCA-Ser-Glu-Val-Asn-Leu-Asp-Ala-Glu-Phe-Arg-Lys(DNP)-Arg-Arg-NH2

Database IDs

• PubChem SID: 162105468
• PubChem CID: 25108649

CALCULATED PROPERTIES

• Acid pKa: 3.164177
• H Acceptors: 38
• H Donor: 29
• LogD (pH = 5.5): -12.258227
• LogD (pH = 7.4): -12.243324
• Log P: -12.243289
• Molar Refractivity: 529.0658 cm^3
• Polarizability: 190.44464 Å^3
• Polar Surface Area: 921.51 Å^2
• Rotatable Bonds: 65
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03BAS131

A fluorogenic substrate for beta-Secretase.

REFERENCES

• Ermolieff, J. et al., Biochem., 39(40):12450 (2000).