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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  verified structure
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/)
References
1. Bang S, Yoo S, Yang TJ, Cho H, Kim YG, Hwang SW. (2010)
Resolvin D1 attenuates activation of sensory transient receptor potential channels leading to multiple anti-nociception.
Br J Pharmacol, 161 (3): 707-20. [PMID:20880407]
2. Bäck M, Powell WS, Dahlén SE, Drazen JM, Evans JF, Serhan CN, Shimizu T, Yokomizo T, Rovati GE. (2014)
Update on leukotriene, lipoxin and oxoeicosanoid receptors: IUPHAR Review 7.
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3. Chiang N, Fredman G, Bäckhed F, Oh SF, Vickery T, Schmidt BA, Serhan CN. (2012)
Infection regulates pro-resolving mediators that lower antibiotic requirements.
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Local and systemic delivery of a stable aspirin-triggered lipoxin prevents neutrophil recruitment in vivo.
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5. Codagnone M, Cianci E, Lamolinara A, Mari VC, Nespoli A, Isopi E, Mattoscio D, Arita M, Bragonzi A, Iezzi M et al.. (2018)
Resolvin D1 enhances the resolution of lung inflammation caused by long-term Pseudomonas aeruginosa infection.
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6. Colby JK, Abdulnour RE, Sham HP, Dalli J, Colas RA, Winkler JW, Hellmann J, Wong B, Cui Y, El-Chemaly S et al.. (2016)
Resolvin D3 and Aspirin-Triggered Resolvin D3 Are Protective for Injured Epithelia.
Am J Pathol, 186 (7): 1801-1813. [PMID:27171898]
7. Davenport AP, Alexander SP, Sharman JL, Pawson AJ, Benson HE, Monaghan AE, Liew WC, Mpamhanga CP, Bonner TI, Neubig RR et al.. (2013)
International Union of Basic and Clinical Pharmacology. LXXXVIII. G protein-coupled receptor list: recommendations for new pairings with cognate ligands.
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8. De Yang, Chen Q, Schmidt AP, Anderson GM, Wang JM, Wooters J, Oppenheim JJ, Chertov O. (2000)
LL-37, the neutrophil granule- and epithelial cell-derived cathelicidin, utilizes formyl peptide receptor-like 1 (FPRL1) as a receptor to chemoattract human peripheral blood neutrophils, monocytes, and T cells.
J Exp Med, 192 (7): 1069-74. [PMID:11015447]
9. Fiore S, Maddox JF, Perez HD, Serhan CN. (1994)
Identification of a human cDNA encoding a functional high affinity lipoxin A4 receptor.
J Exp Med, 180 (1): 253-60. [PMID:8006586]
10. Fiore S, Serhan CN. (1995)
Lipoxin A4 receptor activation is distinct from that of the formyl peptide receptor in myeloid cells: inhibition of CD11/18 expression by lipoxin A4-lipoxin A4 receptor interaction.
Biochemistry, 34 (51): 16678-86. [PMID:8527441]
11. Gabl M, Sundqvist M, Holdfeldt A, Lind S, Mårtensson J, Christenson K, Marutani T, Dahlgren C, Mukai H, Forsman H. (2018)
Mitocryptides from Human Mitochondrial DNA-Encoded Proteins Activate Neutrophil Formyl Peptide Receptors: Receptor Preference and Signaling Properties.
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12. García RA, Lupisella JA, Ito BR, Hsu MY, Fernando G, Carson NL, Allocco JJ, Ryan CS, Zhang R, Wang Z et al.. (2021)
Selective FPR2 Agonism Promotes a Proresolution Macrophage Phenotype and Improves Cardiac Structure-Function Post Myocardial Infarction.
JACC Basic Transl Sci, 6 (8): 676-689. [PMID:34466754]
13. Gronert K, Martinsson-Niskanen T, Ravasi S, Chiang N, Serhan CN. (2001)
Selectivity of recombinant human leukotriene D(4), leukotriene B(4), and lipoxin A(4) receptors with aspirin-triggered 15-epi-LXA(4) and regulation of vascular and inflammatory responses.
Am J Pathol, 158 (1): 3-9. [PMID:11141472]
14. Krishnamoorthy S, Recchiuti A, Chiang N, Yacoubian S, Lee CH, Yang R, Petasis NA, Serhan CN. (2010)
Resolvin D1 binds human phagocytes with evidence for proresolving receptors.
Proc Natl Acad Sci USA, 107 (4): 1660-5. [PMID:20080636]
15. Le Y, Gong W, Li B, Dunlop NM, Shen W, Su SB, Ye RD, Wang JM. (1999)
Utilization of two seven-transmembrane, G protein-coupled receptors, formyl peptide receptor-like 1 and formyl peptide receptor, by the synthetic hexapeptide WKYMVm for human phagocyte activation.
J Immunol, 163 (12): 6777-84. [PMID:10586077]
16. Lin H, Ma C, Cai K, Guo L, Wang X, Lv L, Zhang C, Lin J, Zhang D, Ye C et al.. (2025)
Metabolic signaling of ceramides through the FPR2 receptor inhibits adipocyte thermogenesis.
Science, 388 (6746): eado4188. [PMID:40080544]
17. Park CK, Xu ZZ, Liu T, Lü N, Serhan CN, Ji RR. (2011)
Resolvin D2 is a potent endogenous inhibitor for transient receptor potential subtype V1/A1, inflammatory pain, and spinal cord synaptic plasticity in mice: distinct roles of resolvin D1, D2, and E1.
J Neurosci, 31 (50): 18433-8. [PMID:22171045]
18. Peng C, Vecchio EA, Nguyen ATN, De Seram M, Tang R, Keov P, Woodman OL, Chen YC, Baell J, May LT et al.. (2024)
Biased receptor signalling and intracellular trafficking profiles of structurally distinct formylpeptide receptor 2 agonists.
Br J Pharmacol, 181 (22): 4677-4692. [PMID:39154373]
19. Perretti M, Flower RJ. (1995)
Anti-inflammatory lipocortin-derived peptides.
Agents Actions Suppl, 46: 131-8. [PMID:7610983]
20. Qin CX, May LT, Li R, Cao N, Rosli S, Deo M, Alexander AE, Horlock D, Bourke JE, Yang YH et al.. (2017)
Small-molecule-biased formyl peptide receptor agonist compound 17b protects against myocardial ischaemia-reperfusion injury in mice.
Nat Commun, 8: 14232. [PMID:28169296]
21. Rabiet MJ, Huet E, Boulay F. (2005)
Human mitochondria-derived N-formylated peptides are novel agonists equally active on FPR and FPRL1, while Listeria monocytogenes-derived peptides preferentially activate FPR.
Eur J Immunol, 35 (8): 2486-95. [PMID:16025565]
22. Southern C, Cook JM, Neetoo-Isseljee Z, Taylor DL, Kettleborough CA, Merritt A, Bassoni DL, Raab WJ, Quinn E, Wehrman TS et al.. (2013)
Screening β-Arrestin Recruitment for the Identification of Natural Ligands for Orphan G-Protein-Coupled Receptors.
J Biomol Screen, 18 (5): 599-609. [PMID:23396314]
23. Su SB, Gong W, Gao JL, Shen W, Murphy PM, Oppenheim JJ, Wang JM. (1999)
A seven-transmembrane, G protein-coupled receptor, FPRL1, mediates the chemotactic activity of serum amyloid A for human phagocytic cells.
J Exp Med, 189 (2): 395-402. [PMID:9892621]
24. Takano T, Fiore S, Maddox JF, Brady HR, Petasis NA, Serhan CN. (1997)
Aspirin-triggered 15-epi-lipoxin A4 (LXA4) and LXA4 stable analogues are potent inhibitors of acute inflammation: evidence for anti-inflammatory receptors.
J Exp Med, 185 (9): 1693-704. [PMID:9151906]
25. Zhang MJ, Sansbury BE, Hellmann J, Baker JF, Guo L, Parmer CM, Prenner JC, Conklin DJ, Bhatnagar A, Creager MA et al.. (2016)
Resolvin D2 Enhances Postischemic Revascularization While Resolving Inflammation.
Circulation, 134 (9): 666-680. [PMID:27507404]