apamin   Click here for help

GtoPdb Ligand ID: 2311

Compound class: Peptide
Comment: Expressed by the venom gland of the honeybee (Apis mellifera)
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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

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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 NCCCCC1NC(=O)C2CSSCC(NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(NC(=O)C(CSSCC(C(=O)NC(C(=O)N2)CC(=O)N)N)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C2N(C(=O)C(NC1=O)C)CCC2)CCC(=O)O)C(O)C)C)CC(C)C)C)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)Cc1cnc[nH]1)CCC(=O)N)CCC(=O)N
Isomeric SMILES NCCCC[C@@H]1NC(=O)[C@@H]2CSSC[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC1=O)C)CCC2)CCC(=O)O)[C@H](O)C)C)CC(C)C)C)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1cnc[nH]1)CCC(=O)N)CCC(=O)N
InChI InChI=1S/C79H131N31O24S4/c1-35(2)26-49-70(127)107-51-31-136-135-30-41(81)63(120)105-50(28-57(84)114)71(128)108-53(73(130)99-42(12-7-8-22-80)64(121)96-38(5)77(134)110-25-11-15-54(110)75(132)102-47(18-21-58(115)116)69(126)109-59(39(6)111)76(133)95-37(4)62(119)104-49)33-138-137-32-52(106-66(123)44(14-10-24-92-79(88)89)98-65(122)43(13-9-23-91-78(86)87)97-61(118)36(3)94-72(51)129)74(131)101-45(16-19-55(82)112)67(124)100-46(17-20-56(83)113)68(125)103-48(60(85)117)27-40-29-90-34-93-40/h29,34-39,41-54,59,111H,7-28,30-33,80-81H2,1-6H3,(H2,82,112)(H2,83,113)(H2,84,114)(H2,85,117)(H,90,93)(H,94,129)(H,95,133)(H,96,121)(H,97,118)(H,98,122)(H,99,130)(H,100,124)(H,101,131)(H,102,132)(H,103,125)(H,104,119)(H,105,120)(H,106,123)(H,107,127)(H,108,128)(H,109,126)(H,115,116)(H4,86,87,91)(H4,88,89,92)/t36-,37-,38-,39+,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,59-/m0/s1
InChI Key YVIIHEKJCKCXOB-STYWVVQQSA-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. Barfod ET, Moore AL, Lidofsky SD. (2001)
Cloning and functional expression of a liver isoform of the small conductance Ca2+-activated K+ channel SK3.
Am J Physiol, Cell Physiol, 280 (4): C836-42. [PMID:11245600]
2. Church TW, Weatherall KL, Corrêa SA, Prole DL, Brown JT, Marrion NV. (2015)
Preferential assembly of heteromeric small conductance calcium-activated potassium channels.
Eur J Neurosci, 41 (3): 305-15. [PMID:25421315]
3. Hosseini R, Benton DC, Dunn PM, Jenkinson DH, Moss GW. (2001)
SK3 is an important component of K(+) channels mediating the afterhyperpolarization in cultured rat SCG neurones.
J Physiol (Lond.), 535 (Pt 2): 323-34. [PMID:11533126]
4. Jäger H, Adelman JP, Grissmer S. (2000)
SK2 encodes the apamin-sensitive Ca(2+)-activated K(+) channels in the human leukemic T cell line, Jurkat.
FEBS Lett, 469 (2-3): 196-202. [PMID:10713270]
5. Kohler M, Hirschberg B, Bond CT, Kinzie JM, Marrion NV, Maylie J, Adelman JP. (1996)
Small-conductance, calcium-activated potassium channels from mammalian brain.
Science, 273 (5282): 1709-14. [PMID:8781233]
6. Shah M, Haylett DG. (2000)
The pharmacology of hSK1 Ca2+-activated K+ channels expressed in mammalian cell lines.
Br J Pharmacol, 129 (4): 627-30. [PMID:10683185]
7. Stocker M, Hirzel K, D'hoedt D, Pedarzani P. (2004)
Matching molecules to function: neuronal Ca2+-activated K+ channels and afterhyperpolarizations.
Toxicon, 43 (8): 933-49. [PMID:15208027]
8. Strøbaek D, Jørgensen TD, Christophersen P, Ahring PK, Olesen SP. (2000)
Pharmacological characterization of small-conductance Ca(2+)-activated K(+) channels stably expressed in HEK 293 cells.
Br J Pharmacol, 129 (5): 991-9. [PMID:10696100]
9. Terstappen GC, Pula G, Carignani C, Chen MX, Roncarati R. (2001)
Pharmacological characterisation of the human small conductance calcium-activated potassium channel hSK3 reveals sensitivity to tricyclic antidepressants and antipsychotic phenothiazines.
Neuropharmacology, 40 (6): 772-83. [PMID:11369031]
10. Weatherall KL, Goodchild SJ, Jane DE, Marrion NV. (2010)
Small conductance calcium-activated potassium channels: from structure to function.
Prog Neurobiol, 91 (3): 242-55. [PMID:20359520]
11. Wittekindt OH, Visan V, Tomita H, Imtiaz F, Gargus JJ, Lehmann-Horn F, Grissmer S, Morris-Rosendahl DJ. (2004)
An apamin- and scyllatoxin-insensitive isoform of the human SK3 channel.
Mol Pharmacol, 65 (3): 788-801. [PMID:14978258]