(3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S,3R)-2-{[(2S)-1-[(2S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S)-2-{[(2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-(2-aminoacetamido)-5-carbamimidamidopentanamido]hexanamido]hexanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-3-hydroxybutanamido]-3-hydroxybutanamido]-4-methylpentanamido]-3-carbamoylpropanamido]-4-methylpentanamido]-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-4-carbamoylbutanamido]-3-methylbutanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-4-carbamoylbutanamido]-3-carbamoylpropanoic acid; trifluoroacetic acid

• ChemBase ID: 154446
• Molecular Formular: C166H287F3N66O42
• Molecular Mass: 3936.4671896
• Monoisotopic Mass: 3934.23029221
• SMILES: C[C@H]([C@@H](C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(=N)N)NC(=O)CN)O.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.NCCCC[C@@H](C(=O)N[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)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[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)CC(=O)O)CCC(=O)N)CO)CCCNC(=N)N)C(C)C)CCC(=O)N)Cc1ccccc1)CC(C)C)CC(=O)N)CC(C)C)[C@H](O)C)[C@H](O)C)CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CN)CCCNC(=N)N)CCCCN)CCCCN)CCCNC(=N)N)CCCNC(=N)N)CCC(=O)N)CCCNC(=N)N)CCCNC(=N)N)CCCNC(=N)N)CCCNC(=N)N
• InChI: InChI=1S/C164H286N66O40.C2HF3O2/c1-84(2)77-106(140(255)220-109(79-89-33-10-9-11-34-89)153(268)227-73-28-48-112(227)144(259)212-101(55-58-119(171)236)138(253)222-123(86(5)6)155(270)229-75-31-50-114(229)145(260)211-98(43-23-67-197-161(184)185)135(250)221-110(83-231)142(257)209-100(54-57-118(170)235)137(252)216-105(126(173)241)81-122(239)240)217-141(256)108(80-120(172)237)218-139(254)107(78-85(3)4)219-148(263)124(87(7)232)224-149(264)125(88(8)233)223-147(262)115-51-29-72-226(115)150(265)102(44-24-68-198-162(186)187)213-133(248)93(37-14-17-61-167)210-143(258)111-47-27-71-225(111)151(266)104(46-26-70-200-164(190)191)215-146(261)113-49-30-74-228(113)154(269)116-52-32-76-230(116)152(267)103(45-25-69-199-163(188)189)214-134(249)97(42-22-66-196-160(182)183)206-131(246)95(40-20-64-194-158(178)179)207-136(251)99(53-56-117(169)234)208-132(247)96(41-21-65-195-159(180)181)205-130(245)94(39-19-63-193-157(176)177)204-129(244)92(36-13-16-60-166)203-128(243)91(35-12-15-59-165)202-127(242)90(201-121(238)82-168)38-18-62-192-156(174)175;3-2(4,5)1(6)7/h9-11,33-34,84-88,90-116,123-125,231-233H,12-32,35-83,165-168H2,1-8H3,(H2,169,234)(H2,170,235)(H2,171,236)(H2,172,237)(H2,173,241)(H,201,238)(H,202,242)(H,203,243)(H,204,244)(H,205,245)(H,206,246)(H,207,251)(H,208,247)(H,209,257)(H,210,258)(H,211,260)(H,212,259)(H,213,248)(H,214,249)(H,215,261)(H,216,252)(H,217,256)(H,218,254)(H,219,263)(H,220,255)(H,221,250)(H,222,253)(H,223,262)(H,224,264)(H,239,240)(H4,174,175,192)(H4,176,177,193)(H4,178,179,194)(H4,180,181,195)(H4,182,183,196)(H4,184,185,197)(H4,186,187,198)(H4,188,189,199)(H4,190,191,200);(H,6,7)/t87-,88-,90+,91+,92+,93+,94+,95+,96+,97+,98+,99+,100+,101+,102+,103+,104+,105+,106+,107+,108+,109+,110+,111+,112+,113+,114+,115+,116+,123+,124+,125+;/m1./s1
• InChIKey: OCVQPVVUPFPZLE-NWQCESEKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S,3R)-2-{[(2S)-1-[(2S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S)-2-{[(2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-(2-aminoacetamido)-5-carbamimidamidopentanamido]hexanamido]hexanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-3-hydroxybutanamido]-3-hydroxybutanamido]-4-methylpentanamido]-3-carbamoylpropanamido]-4-methylpentanamido]-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-4-carbamoylbutanamido]-3-methylbutanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-4-carbamoylbutanamido]-3-carbamoylpropanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S,3R)-2-{[(2S)-1-[(2S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S)-2-{[(2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-(2-aminoacetamido)-5-carbamimidamidopentanamido]hexanamido]hexanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-3-hydroxybutanamido]-3-hydroxybutanamido]-4-methylpentanamido]-3-carbamoylpropanamido]-4-methylpentanamido]-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-4-carbamoylbutanamido]-3-methylbutanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-4-carbamoylbutanamido]-3-carbamoylpropanoic acid; trifluoroacetic acid
• Synonyms: L-JNKi 1 trifluoroacetate salt

Database IDs

• MDL Number: MFCD12912420
• PubChem SID: 162248585
• PubChem CID: 71311864

CALCULATED PROPERTIES

• H Acceptors: 71
• H Donor: 64
• LogD (pH = 5.5): -47.151558
• LogD (pH = 7.4): -47.123756
• Log P: -27.828241
• Molar Refractivity: 1061.8123 cm^3
• Polarizability: 376.16467 Å^3
• Polar Surface Area: 1794.88 Å^2
• Rotatable Bonds: 127
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >1 mg/mL
• Apperance: solid; white powder

Safety Information

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

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C164H286N66O40 · xC2HF3O2

DETAILS

Sigma Aldrich - J2580

Amino Acid Sequence
Gly-Arg-Lys-Lys-Arg-Arg-Gln-Arg-Arg-Arg-Pro-Pro-Arg-Pro-Lys-Arg-Pro-Thr-Thr-Leu-Asn-Leu-Phe-Pro-Gln-Val-Pro-Arg-Ser-Gln-Asp-NH2
Biochem/physiol Actions
The L-JNKi 1 and the protease resistant, all-D retro-inverso form, D-JNKi peptides represent the only potent inhibitors specific for JNK (JNK1, JNK2 and JNK3). Different from chemical inhibitors that directly affect kinase activity e.g. by competing with the ATP-binding site of the protein kinase, they rather inhibit the interaction between JNK and its substrate, resulting in a JNK K.O. phenotype. In contrast to pure diffusion they are actively transported into cells, where they remain until their proteolytic degradation. The c-Jun N-terminal kinases (JNK1, 2, 3), members of the mitogen-activated protein kinase (MAPK) superfamily, are activated by a wide variety of extracellular stimuli such as inflammatory cytokines, heat shock and ischemia.Targets of JNKs are mostly transcription factors, including c-Jun, activating transcription factor(ATF) 2, and ETS-containing factors such as Elk1. Other targets having function regulated by JNK-mediated phosphorylation include insulin receptor substrate 1 and Bcl-2.