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gosteganan   Click here for help

GtoPdb Ligand ID: 14105

Synonyms: HPRP-A1 | PL-18
Compound class: Peptide
Comment: Gosteganan is the INN (included in WHO INN proposed list 133, 10th July 2025; formerly PL-18) for a broad-spectrum antimicrobial peptide derived from the N-terminus of the Helicobacter pylori ribosomal protein L1 (RpL1). Gosteganan demonstrates antibacterial activity against both against Gram-negative and Gram-positive bacteria and also has antifungal activity [2]. It is claimed in patent WO2012142855A1 (ProteLight Pharma) [1].
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)C[C@H](C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CC1=CC=CC=C1)C(=O)N[C@H](CO)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CC2=CNC3=C2C=CC=C3)C(=O)N[C@H](CC(=O)N)C(=O)N[C@H](CC4=CNC5=C4C=CC=C5)C(=O)N[C@H](CCCCN)C(=O)N)NC(=O)[C@@H](CCCCN)NC(=O)[C@@H](CCCCN)NC(=O)[C@@H](CC6=CC=CC=C6)NC(=O)C
Isomeric SMILES C([C@H](C(N[C@@H](C(N[C@H](CC=1C=2C(NC1)=CC=CC2)C(N[C@H](CCCCN)C(N)=O)=O)=O)CC(N)=O)=O)NC([C@H](NC([C@H](NC([C@H](NC([C@@H](CC3=CC=CC=C3)NC([C@H](NC([C@H](NC([C@H](NC([C@H](NC([C@H](NC([C@H](NC([C@@H](CC4=CC=CC=C4)NC(C)=O)=O)CCCCN)=O)CCCCN)=O)CC(C)C)=O)CCCCN)=O)CCCCN)=O)CC(C)C)=O)=O)CO)=O)CCCCN)=O)CC(C)C)=O)C=5C=6C(NC5)=CC=CC6
InChI InChI=1S/C103H159N25O18/c1-61(2)50-79(121-92(135)76(41-21-27-47-107)117-91(134)75(40-20-26-46-106)119-98(141)82(114-64(7)130)53-65-30-10-8-11-31-65)95(138)118-74(39-19-25-45-105)90(133)116-77(42-22-28-48-108)93(136)122-80(51-62(3)4)96(139)124-83(54-66-32-12-9-13-33-66)99(142)128-87(60-129)103(146)120-78(43-23-29-49-109)94(137)123-81(52-63(5)6)97(140)125-85(56-68-59-113-72-37-17-15-35-70(68)72)101(144)127-86(57-88(110)131)102(145)126-84(55-67-58-112-71-36-16-14-34-69(67)71)100(143)115-73(89(111)132)38-18-24-44-104/h8-17,30-37,58-59,61-63,73-87,112-113,129H,18-29,38-57,60,104-109H2,1-7H3,(H2,110,131)(H2,111,132)(H,114,130)(H,115,143)(H,116,133)(H,117,134)(H,118,138)(H,119,141)(H,120,146)(H,121,135)(H,122,136)(H,123,137)(H,124,139)(H,125,140)(H,126,145)(H,127,144)(H,128,142)/t73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-/m1/s1
InChI Key MQLNDKCRPLFISR-XNXSXEKGSA-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, Chen M, Huang Y, Li Y, Wang Y, Qu L, Wang W. (2012)
Antibiotic peptide and preparation method therefor and application thereof.
Patent number: WO2012142855A1. Assignee: Jiangsu Protelight Pharmaceutical & Biotechnology. Priority date: 17/01/2012. Publication date: 26/10/2012.
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]