ATLa2

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Ligands
ATLa2

GtoPdb Ligand ID: 3383

Synonyms: ATL analog [15-epi-16-(para-fluoro)-phenoxy-LXA4]

Compound class: Synthetic organic

2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	4
Hydrogen bond donors	3
Rotatable bonds	13
Topological polar surface area	86.99
Molecular weight	404.2
XLogP	4
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

Canonical SMILES	OC(=O)CCCC(C(C=CC=CC=CC=CC(COc1ccc(cc1)F)C)O)O
Isomeric SMILES	OC(=O)CCC[C@@H]([C@@H](/C=C/C=C/C=C\C=C\[C@@H](COc1ccc(cc1)F)C)O)O
InChI	InChI=1S/C23H29FO5/c1-18(17-29-20-15-13-19(24)14-16-20)9-6-4-2-3-5-7-10-21(25)22(26)11-8-12-23(27)28/h2-7,9-10,13-16,18,21-22,25-26H,8,11-12,17H2,1H3,(H,27,28)/b4-2-,5-3+,9-6+,10-7+/t18-,21+,22-/m0/s1
InChI Key	SGFIFYSIHRWSCE-LLXPRBAESA-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. Clish CB, O'Brien JA, Gronert K, Stahl GL, Petasis NA, Serhan CN. (1999) Local and systemic delivery of a stable aspirin-triggered lipoxin prevents neutrophil recruitment in vivo. Proc Natl Acad Sci USA, 96 (14): 8247-52. [PMID:10393980]
2. 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]
3. 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]
4. 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]
5. 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. J Immunol, 200 (9): 3269-3282. [PMID:29602776]
6. 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]
7. 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]
8. Guilford WJ, Bauman JG, Skuballa W, Bauer S, Wei GP, Davey D, Schaefer C, Mallari C, Terkelsen J, Tseng JL et al.. (2004) Novel 3-oxa lipoxin A4 analogues with enhanced chemical and metabolic stability have anti-inflammatory activity in vivo. J Med Chem, 47 (8): 2157-65. [PMID:15056011]
9. 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]
10. 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]
11. 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]
12. Perretti M, Flower RJ. (1995) Anti-inflammatory lipocortin-derived peptides. Agents Actions Suppl, 46: 131-8. [PMID:7610983]
13. 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]
14. 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]
15. 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]
16. 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]

References

1. Clish CB, O'Brien JA, Gronert K, Stahl GL, Petasis NA, Serhan CN. (1999)
Local and systemic delivery of a stable aspirin-triggered lipoxin prevents neutrophil recruitment in vivo.
Proc Natl Acad Sci USA, 96 (14): 8247-52. [PMID:10393980]

2. 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]

3. 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]

4. 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]

5. 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.
J Immunol, 200 (9): 3269-3282. [PMID:29602776]

6. 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]

7. 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]

8. Guilford WJ, Bauman JG, Skuballa W, Bauer S, Wei GP, Davey D, Schaefer C, Mallari C, Terkelsen J, Tseng JL et al.. (2004)
Novel 3-oxa lipoxin A4 analogues with enhanced chemical and metabolic stability have anti-inflammatory activity in vivo.
J Med Chem, 47 (8): 2157-65. [PMID:15056011]

9. 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]

10. 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]

11. 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]

12. Perretti M, Flower RJ. (1995)
Anti-inflammatory lipocortin-derived peptides.
Agents Actions Suppl, 46: 131-8. [PMID:7610983]

13. 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]

14. 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]

15. 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]

16. 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]