Compounds > 1-O-oleoyl-sn-glycero-3-phosphoserine
Page last updated: 2024-11-11

1-O-oleoyl-sn-glycero-3-phosphoserine

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Description

1-O-oleoyl-sn-glycero-3-phosphoserine : A 1-acyl-sn-glycerophosphoserine compound having an oleoyl substituent at the 1-hydroxy position. [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 CID9547099
CHEMBL ID1742484
CHEBI ID52649
SCHEMBL ID15928095

Synonyms (18)

Synonym
1-(9z-octadecenoyl)-sn-glycero-3-phosphoserine
LMGP03050001 ,
ps(18:1/0:0)
ps(18:1(9z)/0:0)
l-serine, 2-hydroxy-3-[(1-oxo-9-octadecenyl)oxy]propyl hydrogen phosphate (ester), [r-(z)]-
lps(18:1)
bdbm50096349
chembl1742484 ,
o-[hydroxy({(2r)-2-hydroxy-3-[(9z)-octadec-9-enoyloxy]propyl}oxy)phosphoryl]-l-serine
CHEBI:52649 ,
1-oleoyl-sn-glycero-3-phosphoserine
1-o-oleoyl-sn-glycero-3-phosphoserine
SCHEMBL15928095
lysops(18:1(9z)/0:0)
(2s)-2-amino-3-[hydroxy-[(2r)-2-hydroxy-3-[(z)-octadec-9-enoyl]oxypropoxy]phosphoryl]oxypropanoic acid
1-oleoyl-sn-glycero-3-phospho-l-serine
JZWNYZVVZXZRRH-YFKVPUFHSA-N
Q27123529
[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]

Protein Targets (8)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
G protein-coupled receptor 34aDanio rerio (zebrafish)EC50 (µMol)0.12940.12880.12940.1300AID1723465
Putative P2Y purinoceptor 10Homo sapiens (human)EC50 (µMol)0.02810.02800.02810.0282AID1226968
Probable G-protein coupled receptor 174Mus musculus (house mouse)EC50 (µMol)0.03390.03390.03390.0340AID1895477
G protein-coupled receptor 34bDanio rerio (zebrafish)EC50 (µMol)0.00350.00350.00350.0035AID1723467
Putative P2Y purinoceptor 10Mus musculus (house mouse)EC50 (µMol)0.02230.01950.02230.0250AID1304958; AID1723459
Probable G-protein coupled receptor 174Homo sapiens (human)EC50 (µMol)0.52240.52000.52240.5248AID1226969
Probable G-protein coupled receptor 34Mus musculus (house mouse)EC50 (µMol)0.29690.23000.29690.4200AID1304957; AID1446540; AID1723456
Probable G-protein coupled receptor 34Homo sapiens (human)EC50 (µMol)1.29290.24550.95153.1623AID1226967; AID1446542; AID1723463
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
positive regulation of Rho protein signal transductionPutative P2Y purinoceptor 10Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayPutative P2Y purinoceptor 10Homo sapiens (human)
negative regulation of interleukin-2 productionProbable G-protein coupled receptor 174Homo sapiens (human)
T cell homeostasisProbable G-protein coupled receptor 174Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayProbable G-protein coupled receptor 174Homo sapiens (human)
positive regulation of Rho protein signal transductionProbable G-protein coupled receptor 174Homo sapiens (human)
G protein-coupled purinergic nucleotide receptor signaling pathwayProbable G-protein coupled receptor 34Homo sapiens (human)
G protein-coupled receptor signaling pathwayProbable G-protein coupled receptor 34Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
G protein-coupled receptor activityPutative P2Y purinoceptor 10Homo sapiens (human)
G protein-coupled receptor activityProbable G-protein coupled receptor 174Homo sapiens (human)
bioactive lipid receptor activityProbable G-protein coupled receptor 174Homo sapiens (human)
G protein-coupled receptor activityProbable G-protein coupled receptor 34Homo sapiens (human)
G protein-coupled purinergic nucleotide receptor activityProbable G-protein coupled receptor 34Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
plasma membranePutative P2Y purinoceptor 10Homo sapiens (human)
plasma membranePutative P2Y purinoceptor 10Homo sapiens (human)
plasma membraneProbable G-protein coupled receptor 174Homo sapiens (human)
centriolar satelliteProbable G-protein coupled receptor 174Homo sapiens (human)
intracellular membrane-bounded organelleProbable G-protein coupled receptor 174Homo sapiens (human)
plasma membraneProbable G-protein coupled receptor 174Homo sapiens (human)
plasma membraneProbable G-protein coupled receptor 34Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID1723458Agonist activity at mouse GPR34 expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis relative to posi2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
AID1723464Agonist activity at human GPR34 expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis relative to cont2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
AID1723466Agonist activity at zebrafish GPR34 type a expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis relat2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
AID1723463Agonist activity at human GPR34 expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
AID1446542Agonist activity at human GPR34 expressed in HEK293 cells co-transfected with AP-TGFalpha/chimeric Galphaq/i1 assessed as induction of AP-TGFalpha release after 1 hr2017Journal of medicinal chemistry, 07-27, Volume: 60, Issue:14
Probing the Hydrophobic Binding Pocket of G-Protein-Coupled Lysophosphatidylserine Receptor GPR34/LPS
AID1446544Agonist activity at mouse GPR34 expressed in HEK293 cells co-transfected with AP-TGFalpha/chimeric Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr relative to control2017Journal of medicinal chemistry, 07-27, Volume: 60, Issue:14
Probing the Hydrophobic Binding Pocket of G-Protein-Coupled Lysophosphatidylserine Receptor GPR34/LPS
AID1446541Intrinsic activity at mouse GPR34 expressed in HEK293 cells co-transfected with AP-TGFalpha/chimeric Galphaq/iL assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr relative to O-(Hydroxy(((2R,3R)-2-(((3-(2-((3-phenoxybenz2017Journal of medicinal chemistry, 07-27, Volume: 60, Issue:14
Probing the Hydrophobic Binding Pocket of G-Protein-Coupled Lysophosphatidylserine Receptor GPR34/LPS
AID1723456Agonist activity at mouse GPR34 expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
AID1723459Agonist activity at mouse P2Y10 expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
AID1226970Agonist activity at mouse P2Y10 receptor expressed in McA-RH7777 cells assessed as actin stress fiber formation at 1 uM after 30 mins by confocal microscopy2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Structure-activity relationships of lysophosphatidylserine analogs as agonists of G-protein-coupled receptors GPR34, P2Y10, and GPR174.
AID1446540Agonist activity at mouse GPR34 expressed in HEK293 cells co-transfected with AP-TGFalpha/chimeric Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr2017Journal of medicinal chemistry, 07-27, Volume: 60, Issue:14
Probing the Hydrophobic Binding Pocket of G-Protein-Coupled Lysophosphatidylserine Receptor GPR34/LPS
AID1723468Agonist activity at zebrafish GPR34 type b expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis relat2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
AID1304959Intrinsic activity at mouse GPR34 expressed in HEK293A cells cotransfected with chimeric Galphaq/il after 1.5 hrs by alkaline phosphatase tagged-TGFalpha shedding assay relative to O-(Hydroxy(((2R,3R)-2-(((3-(2-((3-phenoxybenzyl)oxy)phenyl)-propanoyl)oxy)2016Journal of medicinal chemistry, 04-28, Volume: 59, Issue:8
Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity.
AID1895477Agonist activity at mouse GPR174 transfected in human HEK293FT cells co-transfected with AP-TGFalpha assessed as AP-TGFalpha release incubated for 90 mins by TGFalpha shedding assay
AID1304957Agonist activity at mouse GPR34 expressed in HEK293A cells cotransfected with chimeric Galphaq/il after 1.5 hrs by alkaline phosphatase tagged-TGFalpha shedding assay2016Journal of medicinal chemistry, 04-28, Volume: 59, Issue:8
Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity.
AID1723460Agonist activity at mouse P2Y10 expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis relative to cont2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
AID1304958Agonist activity at mouse P2Y10 receptor expressed in HEK293A cells after 1.5 hrs by alkaline phosphatase tagged-TGFalpha shedding assay2016Journal of medicinal chemistry, 04-28, Volume: 59, Issue:8
Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity.
AID1723467Agonist activity at zebrafish GPR34 type b expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
AID1226969Agonist activity at GPR174 (unknown origin) transfected in HEK293FT cells after 1 hr by TGFalpha shedding assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Structure-activity relationships of lysophosphatidylserine analogs as agonists of G-protein-coupled receptors GPR34, P2Y10, and GPR174.
AID1226968Agonist activity at P2Y10 (unknown origin) transfected in HEK293A cells after 1 hr by TGFalpha shedding assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Structure-activity relationships of lysophosphatidylserine analogs as agonists of G-protein-coupled receptors GPR34, P2Y10, and GPR174.
AID1723465Agonist activity at zebrafish GPR34 type a expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
AID1304960Intrinsic activity at mouse P2Y10 receptor expressed in HEK293A cells after 1.5 hrs by alkaline phosphatase tagged-TGFalpha shedding assay relative to diF-C3-ph-o-O-C112016Journal of medicinal chemistry, 04-28, Volume: 59, Issue:8
Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity.
AID1226967Agonist activity at GPR34 (unknown origin) transfected in HEK293A cells after 1 hr by TGFalpha shedding assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Structure-activity relationships of lysophosphatidylserine analogs as agonists of G-protein-coupled receptors GPR34, P2Y10, and GPR174.
AID1446543Intrinsic activity at human GPR34 expressed in HEK293 cells co-transfected with AP-TGFalpha/chimeric Galphaq/i1 assessed as induction of AP-TGFalpha release after 1 hr relative to O-(Hydroxy(((2R,3R)-2-(((3-(2-((3-phenoxybenzyl)oxy)phenyl)- propanoyl)oxy)2017Journal of medicinal chemistry, 07-27, Volume: 60, Issue:14
Probing the Hydrophobic Binding Pocket of G-Protein-Coupled Lysophosphatidylserine Receptor GPR34/LPS
AID1446545Agonist activity at human GPR34 expressed in HEK293 cells co-transfected with AP-TGFalpha/chimeric Galphaq/i1 assessed as induction of AP-TGFalpha release after 1 hr relative to control2017Journal of medicinal chemistry, 07-27, Volume: 60, Issue:14
Probing the Hydrophobic Binding Pocket of G-Protein-Coupled Lysophosphatidylserine Receptor GPR34/LPS
AID1304963Agonist activity at mouse P2Y10 receptor expressed in rat McA-RH7777 cells assessed as induction of actin stress fiber formation at 100 nM after 30 mins by Alexa fluor 594-labelled phalloidin/DAPI staining based fluorescence microscopy2016Journal of medicinal chemistry, 04-28, Volume: 59, Issue:8
Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity.
AID1723461Agonist activity at mouse P2Y10 expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis relative to posi2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
AID1723457Agonist activity at mouse GPR34 expressed in HEK293 cells co-transfected with AP-TGFalpha/Galphaq/i1 assessed as induction of ectodomain shedding of membrane bound AP-TGFalpha after 1 hr by p-NPP substrate based microplate reader analysis relative to cont2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's3 (60.00)24.3611
2020's2 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.72

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.72 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
ConditionIndicatedRelationship StrengthStudiesTrials