(4S)-4-{[(1S)-1-{[(1S)-1-[({[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(2S,3S)-1-[(2S)-2-[(2S)-2-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-3-carboxy-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}propyl]carbamoyl}butyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}pentyl]carbamoyl}pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamoyl}-2-hydroxypropyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}pentyl]carbamoyl}methyl)carbamoyl]-3-methylbutyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-[(2S,3S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-3-carboxypropanoyl]pyrrolidin-2-yl]formamido}-4-(methylsulfanyl)butanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-3-hydroxybutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]butanoic acid

• ChemBase ID: 155248
• Molecular Formular: C140H227N35O44S
• Molecular Mass: 3136.57348
• Monoisotopic Mass: 3134.63218672
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)O)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CCSC)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC(=O)O)N
• Canonical SMILES: NCCCC[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)N1CCC[C@H]1C(=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)O)C)CC(C)C)CC(C)C)CCC(=O)O)CCCNC(=N)N)Cc1ccc(cc1)O)CCCCN)[C@H](CC)C)[C@H](O)C)C(C)C)CCC(=O)O)CCCNC(=N)N)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC(=O)O)N)CCSC)CO)CO)Cc1ccc(cc1)O)CCC(=O)O)CCC(=O)O)CC(C)C
• InChI: InChI=1S/C140H227N35O44S/c1-17-73(11)109(169-126(206)96(64-79-37-41-81(181)42-38-79)165-133(213)111(76(14)178)171-128(208)98(68-177)167-127(207)97(67-176)166-121(201)91(51-59-220-16)159-129(209)99-32-25-56-173(99)135(215)82(143)65-107(191)192)132(212)160-89(45-49-105(187)188)118(198)156-87(43-47-103(183)184)119(199)161-92(60-69(3)4)113(193)150-66-102(182)152-83(28-19-21-52-141)114(194)153-85(30-23-54-148-139(144)145)115(195)157-90(46-50-106(189)190)122(202)168-108(72(9)10)131(211)172-112(77(15)179)134(214)170-110(74(12)18-2)137(217)175-58-27-34-101(175)136(216)174-57-26-33-100(174)130(210)158-84(29-20-22-53-142)117(197)164-95(63-78-35-39-80(180)40-36-78)125(205)154-86(31-24-55-149-140(146)147)116(196)155-88(44-48-104(185)186)120(200)162-94(62-71(7)8)124(204)163-93(61-70(5)6)123(203)151-75(13)138(218)219/h35-42,69-77,82-101,108-112,176-181H,17-34,43-68,141-143H2,1-16H3,(H,150,193)(H,151,203)(H,152,182)(H,153,194)(H,154,205)(H,155,196)(H,156,198)(H,157,195)(H,158,210)(H,159,209)(H,160,212)(H,161,199)(H,162,200)(H,163,204)(H,164,197)(H,165,213)(H,166,201)(H,167,207)(H,168,202)(H,169,206)(H,170,214)(H,171,208)(H,172,211)(H,183,184)(H,185,186)(H,187,188)(H,189,190)(H,191,192)(H,218,219)(H4,144,145,148)(H4,146,147,149)/t73-,74-,75-,76+,77+,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,108-,109-,110-,111-,112-/m0/s1
• InChIKey: PIPSVIJMEZNWGW-ULDLRERSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-1-[({[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(2S,3S)-1-[(2S)-2-[(2S)-2-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-3-carboxy-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}propyl]carbamoyl}butyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}pentyl]carbamoyl}pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamoyl}-2-hydroxypropyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}pentyl]carbamoyl}methyl)carbamoyl]-3-methylbutyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-[(2S,3S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-3-carboxypropanoyl]pyrrolidin-2-yl]formamido}-4-(methylsulfanyl)butanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-3-hydroxybutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-1-[({[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(2S,3S)-1-[(2S)-2-[(2S)-2-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-3-carboxy-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}propyl]carbamoyl}butyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}pentyl]carbamoyl}pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamoyl}-2-hydroxypropyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}pentyl]carbamoyl}methyl)carbamoyl]-3-methylbutyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-[(2S,3S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-3-carboxypropanoyl]pyrrolidin-2-yl]formamido}-4-(methylsulfanyl)butanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-3-hydroxybutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]butanoic acid
• Synonyms: Calpain Inhibitor Peptide

Database IDs

• CAS Number: 128578-18-7
• MDL Number: MFCD00214571
• PubChem SID: 162249386
• PubChem CID: 16157844

CALCULATED PROPERTIES

• Acid pKa: 2.8409135
• H Acceptors: 53
• H Donor: 44
• LogD (pH = 5.5): -20.714851
• LogD (pH = 7.4): -27.332228
• Log P: -14.89606
• Molar Refractivity: 801.9866 cm^3
• Polarizability: 306.5577 Å^3
• Polar Surface Area: 1277.27 Å^2
• Rotatable Bonds: 102
• 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

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C140H227N35O44S

DETAILS

Sigma Aldrich - C9181

Amino Acid Sequence
Asp-Pro-Met-Ser-Ser-Thr-Tyr-Ile-Glu-Glu-Leu-Gly-Lys-Arg-Glu-Val-Thr-Ile-Pro-Pro-Lys-Tyr-Arg-Glu-Leu-Leu-Ala
Application
Strong inhibitor of Calpain I and II but not of papain or trypsin.