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OP-145   Click here for help

GtoPdb Ligand ID: 13987

Synonyms: P60.4Ac
Compound class: Peptide
Comment: OP-145 is a synthetic antimicrobial peptide based on the sequence of LL-37, that was developed with the aim of increasing the stability and improving the efficacy of the peptide [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)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@H](C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](CC(C)C)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](C(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)NC(=O)C
Isomeric SMILES C([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](CC1=CC=CC=C1)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](CC2=CC=CC=C2)NC([C@@H](NC([C@@H](NC(CNC([C@H]([C@H](CC)C)NC(C)=O)=O)=O)CCCCN)=O)CCC(O)=O)=O)=O)CCCCN)=O)CCCNC(=N)N)=O)[C@H](CC)C)=O)[C@H](C)C)=O)CCC(O)=O)=O)CCCNC(=N)N)=O)[C@H](CC)C)=O)CCCCN)=O)CCCNC(=N)N)=O)=O)CC(C)C)=O)CCCNC(=N)N)=O)CCC(O)=O)=O)CC(C)C)=O)C(C)C)=O)CCCNC(=N)N)(=O)N3[C@H](C(N[C@H](C(N[C@@H](CCCNC(=N)N)C(N)=O)=O)CC(C)C)=O)CCC3
InChI InChI=1S/C142H246N46O31/c1-18-81(14)111(166-84(17)189)131(214)165-75-105(190)167-88(44-27-30-60-143)115(198)174-96(55-58-107(193)194)122(205)182-102(73-85-40-23-21-24-41-85)127(210)172-89(45-28-31-61-144)116(199)170-93(50-36-66-162-140(153)154)124(207)187-113(83(16)20-3)135(218)185-110(80(12)13)132(215)177-97(56-59-108(195)196)120(203)171-94(51-37-67-163-141(155)156)123(206)186-112(82(15)19-2)134(217)176-90(46-29-32-62-145)117(200)169-92(49-35-65-161-139(151)152)119(202)181-103(74-86-42-25-22-26-43-86)128(211)180-99(70-76(4)5)126(209)173-91(48-34-64-160-138(149)150)118(201)175-95(54-57-106(191)192)121(204)179-101(72-78(8)9)129(212)184-109(79(10)11)133(216)178-98(52-38-68-164-142(157)158)136(219)188-69-39-53-104(188)130(213)183-100(71-77(6)7)125(208)168-87(114(146)197)47-33-63-159-137(147)148/h21-26,40-43,76-83,87-104,109-113H,18-20,27-39,44-75,143-145H2,1-17H3,(H2,146,197)(H,165,214)(H,166,189)(H,167,190)(H,168,208)(H,169,200)(H,170,199)(H,171,203)(H,172,210)(H,173,209)(H,174,198)(H,175,201)(H,176,217)(H,177,215)(H,178,216)(H,179,204)(H,180,211)(H,181,202)(H,182,205)(H,183,213)(H,184,212)(H,185,218)(H,186,206)(H,187,207)(H,191,192)(H,193,194)(H,195,196)(H4,147,148,159)(H4,149,150,160)(H4,151,152,161)(H4,153,154,162)(H4,155,156,163)(H4,157,158,164)/t81-,82-,83-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,109-,110-,111-,112-,113-/m0/s1
InChI Key XZVXMKDFYAEMKP-XHBQYZNJSA-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/)
Bioactivity Comments
OP-145 displays similar anti-inflammatory activity to that of LL-37, including lipoteichoic acid and lipopolysaccharide neutralizing activity [2]. OP-145 has Gram-positive antibacterial activity, demonstrating significant in vitro activity against growth and biofilm formation of clinically isolated strains of methicillin-resistant Staphylococcus aureus (MRSA) [1].