PMX53   Click here for help

GtoPdb Ligand ID: 579

Synonyms: Ac-(cyclo-2,6)-F-[OPdChaWR] | PMX 53 | PMX-53
Compound class: Peptide
Comment: PMX53 is a C5aR antagonist [1,3].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

PMX53 is commercially available from our sponsors

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 NC(=NCCCC1NC(=O)C(NC(=O)C(CC2CCCCC2)NC(=O)C2N(C(=O)C(CCCNC1=O)NC(=O)C(Cc1ccccc1)NC(=O)C)CCC2)Cc1c[nH]c2c1cccc2)N
Isomeric SMILES NC(=NCCC[C@@H]1NC(=O)[C@@H](NC(=O)[C@@H](CC2CCCCC2)NC(=O)[C@H]2N(C(=O)[C@H](CCCNC1=O)NC(=O)[C@H](Cc1ccccc1)NC(=O)C)CCC2)Cc1c[nH]c2c1cccc2)N
InChI InChI=1S/C47H65N11O7/c1-29(59)53-37(25-30-13-4-2-5-14-30)42(61)55-36-20-11-22-50-41(60)35(19-10-23-51-47(48)49)54-44(63)39(27-32-28-52-34-18-9-8-17-33(32)34)56-43(62)38(26-31-15-6-3-7-16-31)57-45(64)40-21-12-24-58(40)46(36)65/h2,4-5,8-9,13-14,17-18,28,31,35-40,52H,3,6-7,10-12,15-16,19-27H2,1H3,(H,50,60)(H,53,59)(H,54,63)(H,55,61)(H,56,62)(H,57,64)(H4,48,49,51)/t35-,36-,37-,38+,39-,40-/m0/s1
InChI Key YOKBGCTZYPOSQM-HPSWDUTRSA-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. Lillegard KE, Loeks-Johnson AC, Opacich JW, Peterson JM, Bauer AJ, Elmquist BJ, Regal RR, Gilbert JS, Regal JF. (2014)
Differential effects of complement activation products c3a and c5a on cardiovascular function in hypertensive pregnant rats.
J Pharmacol Exp Ther, 351 (2): 344-51. [PMID:25150279]
2. March DR, Proctor LM, Stoermer MJ, Sbaglia R, Abbenante G, Reid RC, Woodruff TM, Wadi K, Paczkowski N, Tyndall JD et al.. (2004)
Potent cyclic antagonists of the complement C5a receptor on human polymorphonuclear leukocytes. Relationships between structures and activity.
Mol Pharmacol, 65 (4): 868-79. [PMID:15044616]
3. Tamamis P, Kieslich CA, Nikiforovich GV, Woodruff TM, Morikis D, Archontis G. (2014)
Insights into the mechanism of C5aR inhibition by PMX53 via implicit solvent molecular dynamics simulations and docking.
BMC Biophys, 7: 5. [PMID:25170421]
4. Woodruff TM, Strachan AJ, Sanderson SD, Monk PN, Wong AK, Fairlie DP, Taylor SM. (2001)
Species dependence for binding of small molecule agonist and antagonists to the C5a receptor on polymorphonuclear leukocytes.
Inflammation, 25 (3): 171-7. [PMID:11403208]