resolvin D1   Click here for help

GtoPdb Ligand ID: 3934

Abbreviated name: RvD1
Synonyms: 7S,8R,17S‐trihydroxy‐4Z,9E,11E,13Z,15E,19Z‐docosahexaenoic acid
Immunopharmacology Ligand
Compound class: Metabolite
Comment: This is a D (docosahexaenoic acid) series resolvin. There is some ambiguity in the literature and on online resources as to the exact stereochemistry of resolvin D1. The structure shown here is the same as that shown in the PubChem entry linked to above, while other common representations include CID 44251266 and CID 16061135.
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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
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 5
Hydrogen bond donors 4
Rotatable bonds 14
Topological polar surface area 97.99
Molecular weight 376.22
XLogP 3.23
No. Lipinski's rules broken 1

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 CCC=CCC(C=CC=CC=CC=CC(C(CC=CCCC(=O)O)O)O)O
Isomeric SMILES CC/C=C\C[C@@H](/C=C/C=C\C=C\C=C\[C@@H]([C@H](C/C=C\CCC(=O)O)O)O)O
InChI InChI=1S/C22H32O5/c1-2-3-9-14-19(23)15-10-6-4-5-7-11-16-20(24)21(25)17-12-8-13-18-22(26)27/h3-12,15-16,19-21,23-25H,2,13-14,17-18H2,1H3,(H,26,27)/b6-4-,7-5+,9-3-,12-8-,15-10+,16-11+/t19-,20-,21-/m0/s1
InChI Key OIWTWACQMDFHJG-LDOXQWQISA-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
FPR2
GPR32
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
FPR2 Ligand is endogenous in the given species Hs Agonist Full agonist ~11.9 pEC50 - 11
⤷ pEC50 ~11.9 (EC50 ~1.2x10-12 M) [11]
GPR32 Ligand is endogenous in the given species Hs Agonist Full agonist 11.1 pEC50 - 11
⤷ pEC50 11.1 (EC50 8.8x10-12 M) [11]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPA1 Ligand is endogenous in the given species Mm Gating inhibitor Inhibition 7.2 pIC50 - 1,12
⤷ pIC50 7.2 [1,12]
Description: Calcium imaging, patch clamp
Conditions: Mouse DRG neurons, mustard oil AITC (300 µM); HEK293T cells transfected with mTRPs
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at GPR32 resolvin D1 > LXA4
Potency order of endogenous and other ligands at FPR2 LXA4 = aspirin triggered lipoxin A4 = ATLa2 = resolvin D1 > LTC4 = LTD4 >> 15-deoxy-LXA4 >> fMet-Leu-Phe 4,8-10,14
Targets where the ligand is described in the comment field
Target Comment
GPR32 Resolvin D1 has been demonstrated to activate GPR32 in two publications [3,11]. The pairing was not replicated in a recent study based on arrestin recruitment [13]. GPR32 is a pseudogene in mice and rats. See reviews [2] and [7].
Ligand mentioned in the following text fields
Chemerin receptors overview
Leukotriene receptors comments