12-hydroxyheptadecatrienoic acid   Click here for help

GtoPdb Ligand ID: 6159

Abbreviated name: 12-HHT
Synonyms: 12S-HHTrE
Compound class: Metabolite
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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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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 57.53
Molecular weight 280.2
XLogP 5.03
No. Lipinski's rules broken 2

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/)
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 CCCCCC(C=CC=CCC=CCCCC(=O)O)O
Isomeric SMILES CCCCC[C@@H](/C=C/C=C/C/C=C\CCCC(=O)O)O
InChI InChI=1S/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1
InChI Key KUKJHGXXZWHSBG-WBGSEQOASA-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/)
Natural/Endogenous Targets
Target
BLT2 receptor
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
BLT2 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.7 pEC50 - 2
⤷ pEC50 7.7 (EC50 1.9x10-8 M) [2]
BLT2 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.6 pIC50 - 2
⤷ pIC50 8.6 (IC50 2.8x10-9 M) [2]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at BLT2 receptor 12-hydroxyheptadecatrienoic acid > LTB4 > 12S-HETE = 12S-HPETE > 15S-HETE > 12R-HETE > 20-hydroxy-LTB4 2,6
Targets where the ligand is described in the comment field
Target Comment
mPGES2 Heme-free mPGES2 catalyses the isomerisation of prostaglandin H2 (PGE2) to prostaglandin E2 (PGE2) in the presence of glutathione (GSH); in contrast heme-bound mPGES2 catalyses the degradation of PGH2 to 12-hydroxyheptadecatrienoic acid (HHT) and malondialdehyde (MDA) [3-5]. In colon cancer cells artemisinin has been reported to bind reversibly to mPGES2 (occupying the PGH2 site), with the effect of blocking PGE2 biosynthesis and inhibiting cell proliferation [1].
Ligand mentioned in the following text fields
Leukotriene receptors overview