compstatin   Click here for help

GtoPdb Ligand ID: 9218

Immunopharmacology Ligand
Compound class: Peptide
Comment: Compstatin is a cyclic 13 amino acid peptide inhibitor of complement component 3 (C3) [4-5]. Compstatin and analogues are being examined for immunomodulatory activity [1-2,6] in inflammatory and degenerative diseases [3].

compstatin 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 CCC(C(C(=O)NC1CSSCC(NC(=O)C(CCCN=C(N)N)NC(=O)C(Cc2[nH]cnc2)NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)C(C)C)C(C)C)CCC(=O)N)CC(=O)O)Cc1c[nH]c2c1cccc2)Cc1[nH]cnc1)C(=O)NC(C(=O)N)C(O)C)N)C
Isomeric SMILES CC[C@@H]([C@@H](C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](Cc2[nH]cnc2)NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)C(C)C)C(C)C)CCC(=O)N)CC(=O)O)Cc1c[nH]c2c1cccc2)Cc1[nH]cnc1)C(=O)N[C@H](C(=O)N)[C@H](O)C)N)C
InChI InChI=1S/C66H99N23O17S2/c1-8-32(6)50(68)63(104)86-46-27-108-107-26-45(62(103)89-53(33(7)90)54(69)95)85-56(97)39(14-11-17-74-66(70)71)80-59(100)43(20-36-24-73-29-78-36)83-58(99)42(19-35-23-72-28-77-35)79-48(92)25-76-55(96)41(18-34-22-75-38-13-10-9-12-37(34)38)82-60(101)44(21-49(93)94)84-57(98)40(15-16-47(67)91)81-64(105)51(30(2)3)88-65(106)52(31(4)5)87-61(46)102/h9-10,12-13,22-24,28-33,39-46,50-53,75,90H,8,11,14-21,25-27,68H2,1-7H3,(H2,67,91)(H2,69,95)(H,72,77)(H,73,78)(H,76,96)(H,79,92)(H,80,100)(H,81,105)(H,82,101)(H,83,99)(H,84,98)(H,85,97)(H,86,104)(H,87,102)(H,88,106)(H,89,103)(H,93,94)(H4,70,71,74)/t32-,33+,39-,40-,41-,42-,43-,44-,45-,46-,50-,51-,52-,53-/m0/s1
InChI Key RDTRHBCZFDCUPW-KWICJJCGSA-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. Mastellos DC, Ricklin D, Hajishengallis E, Hajishengallis G, Lambris JD. (2016)
Complement therapeutics in inflammatory diseases: promising drug candidates for C3-targeted intervention.
Mol Oral Microbiol, 31 (1): 3-17. [PMID:26332138]
2. Mastellos DC, Yancopoulou D, Kokkinos P, Huber-Lang M, Hajishengallis G, Biglarnia AR, Lupu F, Nilsson B, Risitano AM, Ricklin D et al.. (2015)
Compstatin: a C3-targeted complement inhibitor reaching its prime for bedside intervention.
Eur J Clin Invest, 45 (4): 423-40. [PMID:25678219]
3. Morgan BP, Harris CL. (2015)
Complement, a target for therapy in inflammatory and degenerative diseases.
Nat Rev Drug Discov, 14 (12): 857-77. [PMID:26493766]
4. Sahu A, Kay BK, Lambris JD. (1996)
Inhibition of human complement by a C3-binding peptide isolated from a phage-displayed random peptide library.
J Immunol, 157 (2): 884-91. [PMID:8752942]
5. Sahu A, Soulika AM, Morikis D, Spruce L, Moore WT, Lambris JD. (2000)
Binding kinetics, structure-activity relationship, and biotransformation of the complement inhibitor compstatin.
J Immunol, 165 (5): 2491-9. [PMID:10946275]
6. Zhang Y, Shao D, Ricklin D, Hilkin BM, Nester CM, Lambris JD, Smith RJ. (2015)
Compstatin analog Cp40 inhibits complement dysregulation in vitro in C3 glomerulopathy.
Immunobiology, 220 (8): 993-8. [PMID:25982307]