peceleganan   Click here for help

GtoPdb Ligand ID: 13758

Synonyms: PL-5 | V681
Compound class: Peptide
Comment: Peceleganan is an α-helical cationic antimicrobial peptide [1-2].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC4=CNC5=C4C=CC=C5)NC(=O)[C@H](CCCCN)NC(=O)C
Isomeric SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC4=CNC5=CC=CC=C54)NC(=O)[C@H](CCCCN)NC(=O)C
InChI InChI=1S/C138H226N36O34/c1-19-76(10)109(135(205)169-107(70-178)133(203)166-104(67-175)113(145)183)171-117(187)80(14)150-118(188)92(47-29-35-53-140)155-124(194)97(58-72(2)3)159-116(186)79(13)152-136(206)110(81(15)179)174-130(200)103(64-88-66-146-71-148-88)163-126(196)99(60-74(6)7)164-134(204)108(75(8)9)170-138(208)112(83(17)181)173-122(192)95(50-32-38-56-143)154-115(185)78(12)149-114(184)77(11)151-131(201)105(68-176)167-120(190)93(48-30-36-54-141)156-127(197)101(62-86-42-24-21-25-43-86)165-137(207)111(82(16)180)172-123(193)96(51-33-39-57-144)158-125(195)98(59-73(4)5)160-128(198)100(61-85-40-22-20-23-41-85)161-132(202)106(69-177)168-121(191)94(49-31-37-55-142)157-129(199)102(63-87-65-147-90-45-27-26-44-89(87)90)162-119(189)91(153-84(18)182)46-28-34-52-139/h20-27,40-45,65-66,71-83,91-112,147,175-181H,19,28-39,46-64,67-70,139-144H2,1-18H3,(H2,145,183)(H,146,148)(H,149,184)(H,150,188)(H,151,201)(H,152,206)(H,153,182)(H,154,185)(H,155,194)(H,156,197)(H,157,199)(H,158,195)(H,159,186)(H,160,198)(H,161,202)(H,162,189)(H,163,196)(H,164,204)(H,165,207)(H,166,203)(H,167,190)(H,168,191)(H,169,205)(H,170,208)(H,171,187)(H,172,193)(H,173,192)(H,174,200)/t76-,77-,78-,79-,80-,81+,82+,83+,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-/m0/s1
InChI Key IUYWAZJIRQDBEJ-XECNVCPKSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Chen Y, Mant CT, Farmer SW, Hancock RE, Vasil ML, Hodges RS. (2005)
Rational design of alpha-helical antimicrobial peptides with enhanced activities and specificity/therapeutic index.
J Biol Chem, 280 (13): 12316-29. [PMID:15677462]
2. Feng Q, Huang Y, Chen M, Li G, Chen Y. (2015)
Functional synergy of α-helical antimicrobial peptides and traditional antibiotics against Gram-negative and Gram-positive bacteria in vitro and in vivo.
Eur J Clin Microbiol Infect Dis, 34 (1): 197-204. [PMID:25169965]
3. Wei Y, Li Y, Li X, Zhao Y, Xu J, Wang H, Rong X, Xiong J, Chen X, Luo G et al.. (2024)
Peceleganan Spray for the Treatment of Skin Wound Infections: A Randomized Clinical Trial.
JAMA Netw Open, 7 (6): e2415310. [PMID:38861260]