Page last updated: 2024-11-13

lysophosphatidylserine

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Description

lysophosphatidylserine: stimulates histamine secretion from isolated mast cells in mouse plasma [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

lysophosphatidylserine : An acylglycerophosphoserine resulting from partial hydrolysis of a phosphatidylserine, which removes one of the fatty acid groups. The structure is depicted in the image where R(1) = acyl, R(2) = H or where R(1) = H, R(2) = acyl. Formula C7H13NO9PR, where R represents the hydrocarbon chain of the fatty acyl group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

1-stearoyl-sn-glycero-3-phosphoserine : A 1-acyl-sn-glycerophosphoserine in which the acyl group is specified as stearoyl (octadecanoyl). [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID42607474
CHEMBL ID582985
CHEBI ID85403
SCHEMBL ID17482440
MeSH IDM0083982

Synonyms (18)

Synonym
lps(18:0)
LMGP03050006
1-octadecanoyl-sn-glycero-3-phosphoserine
ps(18:0/0:0)
lysophosphatidylserine
CHEMBL582985
chebi:85403 ,
lysops
lysophosphatidyl-l-serine
gtpl4064
(2s)-2-amino-3-[hydroxy-[(2r)-2-hydroxy-3-octadecanoyloxypropoxy]phosphoryl]oxypropanoic acid
1-octadecanoyl-sn-glycero-3-phospho-l-serine
o-{hydroxy[(2r)-2-hydroxy-3-(octadecanoyloxy)propoxy]phosphoryl}-l-serine
1-stearoyl-sn-glycero-3-phosphoserine
1-stearoyl-sn-glycero-3-phospho-l-serine
SCHEMBL17482440
lysops(18:0/0:0)
Q27083342

Research Excerpts

Overview

Lysophosphatidylserine (LysoPS) is a lipid mediator that induces multiple cellular responses through binding to GPR174. Its generating enzyme, phosphatidyllserine-specific phospholipase A1 (PS-PLA1), reportedly plays roles in stomach and colon cancers.

ExcerptReferenceRelevance
"Lysophosphatidylserine (LysoPS) is an amphipathic lysophospholipid that mediates a broad spectrum of inflammatory responses through a poorly characterized mechanism. "( Lysophosphatidylserine Induces MUC5AC Production via the Feedforward Regulation of the TACE-EGFR-ERK Pathway in Airway Epithelial Cells in a Receptor-Independent Manner.
Chung, IY; Jo, SH; Kim, C; Kim, HJ; Sim, MS, 2022
)
3.61
"Lysophosphatidylserine (LysoPS) is a lipid mediator that induces multiple cellular responses through binding to GPR174. "( Structural basis of lysophosphatidylserine receptor GPR174 ligand recognition and activation.
Guo, C; He, Y; Huang, Z; Ikuta, T; Inoue, A; Kawakami, K; Liang, J; Qian, Y; Wang, N; Xia, R; Xu, Z; Zhang, A; Zhu, X, 2023
)
2.68
"Lysophosphatidylserine (LysoPS) is a lysophospholipid, its generating enzyme, phosphatidylserine-specific phospholipase A1 (PS-PLA1), reportedly plays roles in stomach and colon cancers. "( Possible involvement of PS-PLA1 and lysophosphatidylserine receptor (LPS1) in hepatocellular carcinoma.
Hasegawa, K; Ikeda, H; Ishizawa, T; Kokudo, N; Kurano, M; Sato, M; Uranbileg, B; Yatomi, Y, 2020
)
2.28
"Lysophosphatidylserine (LysoPS) is an emerging lysophospholipid (LPL) mediator, which acts through G protein-coupled receptors, like lysophosphatidic acid (LPA) and sphingosine 1-phosphate (S1P). "( Current Knowledge on the Biology of Lysophosphatidylserine as an Emerging Bioactive Lipid.
Aoki, J; Kano, K; Omi, J, 2021
)
2.34
"Lysophosphatidylserine (lysoPS) is a type of lysophospholipid mediator, which is involved in allergic conditions and tumor progression. "( Lysophosphatidylserine stimulates chemotactic migration of colorectal cancer cells through GPR34 and PI3K/Akt pathway.
H Tsuno, N; Iida, Y; Ikeda, T; Ishihara, S; Kaneko, K; Kawai, K; Kishikawa, J; Kitayama, J; Murono, K; Sunami, E; Watanabe, T; Yamaguchi, H; Yatomi, Y, 2014
)
3.29
"Lysophosphatidylserines (lyso-PSs) are a class of signaling lipids that regulate immunological and neurological processes. "( Immunomodulatory lysophosphatidylserines are regulated by ABHD16A and ABHD12 interplay.
Bird, TD; Camara, K; Chen, DH; Cravatt, BF; Dix, MM; Howell, AR; Kamat, SS; Parsons, WH, 2015
)
2.2
"Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator generated by hydrolysis of membrane phospholipid phosphatidylserine. "( Structure-activity relationships of lysophosphatidylserine analogs as agonists of G-protein-coupled receptors GPR34, P2Y10, and GPR174.
Aoki, J; Ikubo, M; Inoue, A; Ishiguro, J; Jung, S; Kano, K; Kishi, T; Makide, K; Nakamura, S; Ohwada, T; Okudaira, M; Otani, Y; Sayama, M; Shuto, A; Suzuki, K; Uwamizu, A, 2015
)
2.13
"Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator that specifically activates membrane proteins of the P2Y and its related families of G protein-coupled receptors (GPCR), GPR34 (LPS1), P2Y10 (LPS2), and GPR174 (LPS3). "( Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity.
Aoki, J; Ikubo, M; Inoue, A; Jung, S; Kano, K; Kishi, T; Makide, K; Nakamura, S; Ohwada, T; Otani, Y; Sayama, M; Uwamizu, A, 2016
)
2.13
"Lysophosphatidylserine is a specific inducer of histamine release in isolated mast cells. "( Lysophosphatidylserine as histamine releaser in mice and rats.
Battistella, A; Bigon, E; Boarato, E; Bruni, A; Mietto, L; Toffano, G, 1984
)
3.15

Effects

ExcerptReferenceRelevance
"Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations."( Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
Aoki, J; Arai, H; Ishida, M; Iwashita, M; Makide, K; Misumi, Y; Nonomura, T; Ohwada, T; Otani, Y; Taguchi, R; Tsujimoto, M, 2009
)
1.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
1-acyl-sn-glycero-3-phosphoserineAn sn-glycerophosphoserine compound having an acyl substituent at the 1-hydroxy position.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID445953Increase in MAPK level in CHOK1 cells at 0.01 to 10 uM by Western blotting2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445951Inhibition of forskolin-induced cAMP production in CHOK1 cells at 0.01 to 10 uM after 30 mins by EIA2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445943Effect on hypothermic effect in mast cell-deficient WBB6F1 mouse assessed as reduction in rectal temperature at 10 ug, iv measured every 5 to 10 mins for 60 mins2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445944Activation of mouse GPR34 expressed in CHOK1 cells assessed as inhibition of forskolin-induced cAMP production at 0.01 to 10 uM after 30 mins by EIA2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445772Induction of Wistar rat peritoneal mast cell degradation assessed as anti-DNP IgE-induced histamine release at 0.01 to 10 uM after 15 mins fluorometric assay2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445775Cytotoxicity against concanavalin A-stimulated Wistar rat peritoneal mast cells assessed as LDH release at 50 uM2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445945Activation of mouse GPR34 expressed in CHOK1 cells assessed as increase in intracellular calcium level by spectrofluorimetry2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445948Activation of rat GPR34 expressed in CHOK1 cells assessed as phosphorylated ERK level at 0.01 to 10 uM by Western blotting2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445777Effect on hypothermic effect in C57BL/6 mouse assessed as reduction in rectal temperature at 25 to 100 ug, iv measured every 5 to 10 mins for 60 mins2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445954Stimulation of mouse bone marrow-derived mast cell degranulation2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445768Induction of Wistar rat peritoneal mast cell degradation assessed as concanavalin A-induced histamine release after 15 mins fluorometric assay2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445779Effect on hypothermic effect in Wistar rat assessed as reduction in rectal temperature at 20 to 200 ug, iv measured every 5 to 10 mins for 60 mins2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445952Increase in intracellular calcium level in CHOK1 cells by spectrofluorimetry2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445950Activation of rat GPR34 expressed in CHOK1 cells assessed as total ERK level at 0.01 to 10 uM by Western blotting2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445947Activation of mouse GPR34 expressed in CHOK1 cells assessed as phosphorylated ERK level at 0.01 to 10 uM by Western blotting2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445946Activation of rat GPR34 expressed in CHOK1 cells assessed as increase in intracellular calcium level by spectrofluorimetry2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445769Induction of C57BL/6 mouse peritoneal mast cell degradation assessed as concanavalin A-induced histamine release after 15 mins fluorometric assay2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID445949Activation of mouse GPR34 expressed in CHOK1 cells assessed as total ERK level at 0.01 to 10 uM by Western blotting2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.
AID1345065Mouse GPR34 (Class A Orphans)2006Biochemical and biophysical research communications, Mar-24, Volume: 341, Issue:4
Identification of a lysophosphatidylserine receptor on mast cells.
AID1345077Human GPR34 (Class A Orphans)2006Biochemical and biophysical research communications, Mar-24, Volume: 341, Issue:4
Identification of a lysophosphatidylserine receptor on mast cells.
AID1345387Human GPR174 (Class A Orphans)2012Nature methods, Oct, Volume: 9, Issue:10
TGFα shedding assay: an accurate and versatile method for detecting GPCR activation.
AID1345077Human GPR34 (Class A Orphans)2012Journal of biochemistry, May, Volume: 151, Issue:5
GPR34 is a receptor for lysophosphatidylserine with a fatty acid at the sn-2 position.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (145)

TimeframeStudies, This Drug (%)All Drugs %
pre-199038 (26.21)18.7374
1990's25 (17.24)18.2507
2000's25 (17.24)29.6817
2010's32 (22.07)24.3611
2020's25 (17.24)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.48

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index25.48 (24.57)
Research Supply Index5.01 (2.92)
Research Growth Index4.70 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.48)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews8 (5.37%)6.00%
Case Studies0 (0.00%)4.05%
Observational1 (0.67%)0.25%
Other140 (93.96%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]