Octpep-1   Click here for help

GtoPdb Ligand ID: 12265

Compound class: Peptide
Comment: Octpep-1 is a 12 amino acid peptide that's derived from an octopus venom molecule. It disrupts PI3K/AKT pathway signalling in melanoma cells and produces a cytotoxic effect that is selective for these cells compared to normal fibroblasts [2]. Octpep-1 can induce an antiproliferative effect against aggressive and hard-to-treat melanoma cells that are driven by the BRAFV600E mutation [1]. Although Octpep-1 appears to exhibit (very) weak agonist activity at tachykinin NK1 receptors, it's antiproliferative activity is independent of NK1R expression [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 CSCC[C@@H](C(=O)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CC(=O)O)N)CO)CC(=O)O)CC(=O)O)CCC(=O)O)Cc1ccccc1)CO)CC(C)C
Isomeric SMILES N[C@@H](CC(=O)O)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)O
InChI InChI=1S/C58H86N12O23S/c1-28(2)21-34(48(82)61-33(58(92)93)17-20-94-5)62-53(87)39(27-72)67-55(89)46(29(3)4)68-51(85)35(22-30-11-7-6-8-12-30)63-47(81)32(15-16-42(73)74)60-49(83)36(24-44(77)78)64-50(84)37(25-45(79)80)65-52(86)38(26-71)66-54(88)40-13-9-18-69(40)57(91)41-14-10-19-70(41)56(90)31(59)23-43(75)76/h6-8,11-12,28-29,31-41,46,71-72H,9-10,13-27,59H2,1-5H3,(H,60,83)(H,61,82)(H,62,87)(H,63,81)(H,64,84)(H,65,86)(H,66,88)(H,67,89)(H,68,85)(H,73,74)(H,75,76)(H,77,78)(H,79,80)(H,92,93)/t31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,46-/m0/s1
InChI Key GKODHHDFYJUXTK-HVCWXIAISA-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. Moral-Sanz J, Fernandez-Rojo MA, Colmenarejo G, Kurdyukov S, Brust A, Ragnarsson L, Andersson Å, Vila SF, Cabezas-Sainz P, Wilhelm P et al.. (2022)
The structural conformation of the tachykinin domain drives the anti-tumoural activity of an octopus peptide in melanoma BRAFV600E.
Br J Pharmacol, 179 (20): 4878-4896. [PMID:35818835]
2. Moral-Sanz J, Fernandez-Rojo MA, Potriquet J, Mukhopadhyay P, Brust A, Wilhelm P, Smallwood TB, Clark RJ, Fry BG, Alewood PF et al.. (2021)
ERK and mTORC1 Inhibitors Enhance the Anti-Cancer Capacity of the Octpep-1 Venom-Derived Peptide in Melanoma BRAF(V600E) Mutations.
Toxins (Basel), 13 (2): 146. [PMID:33672955]