(4S)-4-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-hydroxy-1-{[(2S)-1-oxo-3-phenyl-1-[(2S)-2-({2-[(5-sulfonaphthalen-1-yl)amino]ethyl}carbamoyl)pyrrolidin-1-yl]propan-2-yl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}pentyl]carbamoyl}butyl]carbamoyl}-4-[(4-{2-[4-(dimethylamino)phenyl]diazen-1-yl}phenyl)formamido]butanoic acid; trifluoroacetic acid

• ChemBase ID: 154696
• Molecular Formular: C78H99F3N16O17S
• Molecular Mass: 1621.7778696
• Monoisotopic Mass: 1620.70469145
• SMILES: CCCC[C@@H](C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)NCCNc1cccc2c1cccc2S(=O)(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)O)NC(=O)c1ccc(cc1)/N=N/c1ccc(cc1)N(C)C.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.CCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)NCCNc1cccc2c1cccc2S(=O)(=O)O)Cc1ccccc1)CO)CC(C)C)Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)c1ccc(cc1)/N=N/c1ccc(cc1)N(C)C)CCC(=O)O)CCCNC(=N)N
• InChI: InChI=1S/C76H98N16O15S.C2HF3O2/c1-6-7-24-57(83-68(97)58(26-16-39-81-76(77)78)84-70(99)59(37-38-66(94)95)82-67(96)50-29-31-51(32-30-50)89-90-52-33-35-53(36-34-52)91(4)5)69(98)86-61(44-48-18-10-8-11-19-48)72(101)85-60(43-47(2)3)71(100)88-63(46-93)73(102)87-62(45-49-20-12-9-13-21-49)75(104)92-42-17-27-64(92)74(103)80-41-40-79-56-25-14-23-55-54(56)22-15-28-65(55)108(105,106)107;3-2(4,5)1(6)7/h8-15,18-23,25,28-36,47,57-64,79,93H,6-7,16-17,24,26-27,37-46H2,1-5H3,(H,80,103)(H,82,96)(H,83,97)(H,84,99)(H,85,101)(H,86,98)(H,87,102)(H,88,100)(H,94,95)(H4,77,78,81)(H,105,106,107);(H,6,7)/t57-,58-,59-,60-,61-,62-,63-,64-;/m0./s1
• InChIKey: NNUMUURWINZVDB-LPNJBUSOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-hydroxy-1-{[(2S)-1-oxo-3-phenyl-1-[(2S)-2-({2-[(5-sulfonaphthalen-1-yl)amino]ethyl}carbamoyl)pyrrolidin-1-yl]propan-2-yl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}pentyl]carbamoyl}butyl]carbamoyl}-4-[(4-{2-[4-(dimethylamino)phenyl]diazen-1-yl}phenyl)formamido]butanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-hydroxy-1-{[(2S)-1-oxo-3-phenyl-1-[(2S)-2-({2-[(5-sulfonaphthalen-1-yl)amino]ethyl}carbamoyl)pyrrolidin-1-yl]propan-2-yl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}pentyl]carbamoyl}butyl]carbamoyl}-4-[(4-{2-[4-(dimethylamino)phenyl]diazen-1-yl}phenyl)formamido]butanoic acid; trifluoroacetic acid
• Synonyms: N-[4-[[4-(Dimethylamino)phenyl]azo]benzoyl]-L-α-glutamyl-L-arginyl-L-norleucyl-L-phenylalanyl-L-leucyl-L-seryl-L-phenylalanyl-N-[2-[(5-sulfo-1-naphthalenyl)amino]ethyl]-L-prolinamide trifluoroacetate salt; DABCYL-Glu-Arg-Nle-Phe-Leu-Ser-Phe-Pro-EDANS trifluoroacetate salt

Database IDs

• CAS Number: 263718-22-5(freeacid)
• MDL Number: MFCD19053157
• PubChem SID: 162248834
• PubChem CID: 71311942

CALCULATED PROPERTIES

• Acid pKa: -1.733384
• H Acceptors: 22
• H Donor: 15
• LogD (pH = 5.5): 2.2448845
• LogD (pH = 7.4): 0.81683743
• Log P: 3.253191
• Molar Refractivity: 418.602 cm^3
• Polarizability: 156.25162 Å^3
• Polar Surface Area: 466.9 Å^2
• Rotatable Bonds: 42
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C76H98N16O15S1 · xC2HF3O2

DETAILS

Sigma Aldrich - 07082

Biochem/physiol Actions
Peptide substrate for the assay of malaria aspartylproteinase, peptide sequence derived from the cleavage site present in hemoglobin, with norleucine as a substitution for methionine in order to avoid problems related to oxidation1.