Page last updated: 2024-11-12

VPC 23019

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

VPC23019: inhibits S1P3 receptor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

VPC 23019 : A secondary carboxamide resulting from the formal condensation of the carboxy group of O-phospho-D-serine with the amino group of m-octylaniline. An analogue of sphingosine-1-phosphate (S1P), it is a potent antagonist for both S1P1 and S1P3 receptors. It can inhibit S1P-induced migration of thyroid cancer cells, ovarian cancer cells, and neural stem cells. [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 CID11588811
CHEMBL ID228102
CHEBI ID144948
SCHEMBL ID12881971

Synonyms (28)

Synonym
[(2r)-2-amino-2-[(3-octylphenyl)carbamoyl]ethoxy]phosphonic acid
bdbm50198833
(r)-2-amino-3-(3-octylphenylamino)-3-oxopropyl dihydrogen phosphate
CHEMBL228102 ,
(2r)-2-amino-3-(3-octylanilino)-3-oxopropyl dihydrogen phosphate
vpc 23019
vpc-23019
449173-19-7
CHEBI:144948
(r)-phosphoric acid mono-[2-amino-2-(3-octyl-phenylcarbamoyl)-ethyl] ester
(2r)-2-amino-n-(3-octylphenyl)-3-(phosphonooxy)-propanamide
vpc23019
n-(3-octylphenyl)-o-phosphono-d-serinamide
gtpl3324
(r)-2-amino-3-((3-octylphenyl)amino)-3-oxopropyl dihydrogen phosphate ,
SCHEMBL12881971
2-amino-n-(3-octylphenyl)-3-(phosphonooxy)-propanamaide
AKOS024458026
HY-108490
Q27089156
AS-16597
CS-0028980
EX-A4712
A899698
ZSA17319
[(2r)-2-amino-3-(3-octylanilino)-3-oxopropyl] dihydrogen phosphate
AC-36622
2-amino-n-(3-octylphenyl)-3-(phosph onooxy)-propanamaide
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
sphingosine-1-phosphate receptor 3 antagonistAny sphingosine-1-phosphate receptor (S1PR) antagonist that acts as an antagonist towards the subtype 3 receptors (S1PR3).
sphingosine-1-phosphate receptor 1 antagonistAny sphingosine-1-phosphate receptor (S1PR) antagonist that acts as an antagonist for the subtype 1 receptors (S1PR1).
[role 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]

Drug Classes (5)

ClassDescription
D-serine derivativeA non-proteinogenic amino acid derivative resulting from reaction of D-serine at the amino group or the carboxy group, or from the replacement of any hydrogen of D-serine by a heteroatom.
secondary carboxamideA carboxamide resulting from the formal condensation of a carboxylic acid with a primary amine; formula RC(=O)NHR(1).
organic phosphate
phosphoric ester
aromatic amideAn amide in which the amide linkage is bonded directly to an aromatic system.
[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 (4)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sphingosine 1-phosphate receptor 4Homo sapiens (human)EC50 (µMol)0.50000.00010.26263.2500AID284812
Sphingosine 1-phosphate receptor 1Homo sapiens (human)EC50 (µMol)0.05800.00000.17597.8700AID284809
Sphingosine 1-phosphate receptor 3Homo sapiens (human)EC50 (µMol)0.45000.00010.30925.0000AID284811
Sphingosine 1-phosphate receptor 5Homo sapiens (human)EC50 (µMol)0.05200.00020.13653.1623AID284813
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (40)

Processvia Protein(s)Taxonomy
sphingosine-1-phosphate receptor signaling pathwaySphingosine 1-phosphate receptor 4Homo sapiens (human)
immune responseSphingosine 1-phosphate receptor 4Homo sapiens (human)
G protein-coupled receptor signaling pathwaySphingosine 1-phosphate receptor 4Homo sapiens (human)
activation of phospholipase C activitySphingosine 1-phosphate receptor 4Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationSphingosine 1-phosphate receptor 4Homo sapiens (human)
regulation of metabolic processSphingosine 1-phosphate receptor 4Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwaySphingosine 1-phosphate receptor 4Homo sapiens (human)
blood vessel maturationSphingosine 1-phosphate receptor 1Homo sapiens (human)
cardiac muscle tissue growth involved in heart morphogenesisSphingosine 1-phosphate receptor 1Homo sapiens (human)
sphingosine-1-phosphate receptor signaling pathwaySphingosine 1-phosphate receptor 1Homo sapiens (human)
chemotaxisSphingosine 1-phosphate receptor 1Homo sapiens (human)
cell adhesionSphingosine 1-phosphate receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathwaySphingosine 1-phosphate receptor 1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwaySphingosine 1-phosphate receptor 1Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwaySphingosine 1-phosphate receptor 1Homo sapiens (human)
brain developmentSphingosine 1-phosphate receptor 1Homo sapiens (human)
cell population proliferationSphingosine 1-phosphate receptor 1Homo sapiens (human)
cell migrationSphingosine 1-phosphate receptor 1Homo sapiens (human)
transmission of nerve impulseSphingosine 1-phosphate receptor 1Homo sapiens (human)
lamellipodium assemblySphingosine 1-phosphate receptor 1Homo sapiens (human)
actin cytoskeleton organizationSphingosine 1-phosphate receptor 1Homo sapiens (human)
regulation of cell adhesionSphingosine 1-phosphate receptor 1Homo sapiens (human)
neuron differentiationSphingosine 1-phosphate receptor 1Homo sapiens (human)
positive regulation of cell migrationSphingosine 1-phosphate receptor 1Homo sapiens (human)
regulation of bone mineralizationSphingosine 1-phosphate receptor 1Homo sapiens (human)
leukocyte chemotaxisSphingosine 1-phosphate receptor 1Homo sapiens (human)
regulation of bone resorptionSphingosine 1-phosphate receptor 1Homo sapiens (human)
endothelial cell differentiationSphingosine 1-phosphate receptor 1Homo sapiens (human)
positive regulation of transcription by RNA polymerase IISphingosine 1-phosphate receptor 1Homo sapiens (human)
positive regulation of smooth muscle cell proliferationSphingosine 1-phosphate receptor 1Homo sapiens (human)
positive regulation of positive chemotaxisSphingosine 1-phosphate receptor 1Homo sapiens (human)
negative regulation of stress fiber assemblySphingosine 1-phosphate receptor 1Homo sapiens (human)
heart trabecula morphogenesisSphingosine 1-phosphate receptor 1Homo sapiens (human)
T cell migrationSphingosine 1-phosphate receptor 1Homo sapiens (human)
angiogenesisSphingosine 1-phosphate receptor 1Homo sapiens (human)
regulation of metabolic processSphingosine 1-phosphate receptor 1Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwaySphingosine 1-phosphate receptor 1Homo sapiens (human)
sphingosine-1-phosphate receptor signaling pathwaySphingosine 1-phosphate receptor 3Homo sapiens (human)
inflammatory responseSphingosine 1-phosphate receptor 3Homo sapiens (human)
G protein-coupled receptor signaling pathwaySphingosine 1-phosphate receptor 3Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwaySphingosine 1-phosphate receptor 3Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationSphingosine 1-phosphate receptor 3Homo sapiens (human)
Notch signaling pathwaySphingosine 1-phosphate receptor 3Homo sapiens (human)
positive regulation of cell population proliferationSphingosine 1-phosphate receptor 3Homo sapiens (human)
anatomical structure morphogenesisSphingosine 1-phosphate receptor 3Homo sapiens (human)
regulation of interleukin-1 beta productionSphingosine 1-phosphate receptor 3Homo sapiens (human)
negative regulation of establishment of endothelial barrierSphingosine 1-phosphate receptor 3Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwaySphingosine 1-phosphate receptor 3Homo sapiens (human)
regulation of metabolic processSphingosine 1-phosphate receptor 3Homo sapiens (human)
sphingosine-1-phosphate receptor signaling pathwaySphingosine 1-phosphate receptor 5Homo sapiens (human)
regulation of neuron differentiationSphingosine 1-phosphate receptor 5Homo sapiens (human)
regulation of metabolic processSphingosine 1-phosphate receptor 5Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwaySphingosine 1-phosphate receptor 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
protein bindingSphingosine 1-phosphate receptor 4Homo sapiens (human)
lipid bindingSphingosine 1-phosphate receptor 4Homo sapiens (human)
sphingosine-1-phosphate receptor activitySphingosine 1-phosphate receptor 4Homo sapiens (human)
G protein-coupled receptor activitySphingosine 1-phosphate receptor 4Homo sapiens (human)
G protein-coupled receptor bindingSphingosine 1-phosphate receptor 1Homo sapiens (human)
G protein-coupled receptor activitySphingosine 1-phosphate receptor 1Homo sapiens (human)
protein bindingSphingosine 1-phosphate receptor 1Homo sapiens (human)
sphingosine-1-phosphate receptor activitySphingosine 1-phosphate receptor 1Homo sapiens (human)
sphingolipid bindingSphingosine 1-phosphate receptor 1Homo sapiens (human)
integrin bindingSphingosine 1-phosphate receptor 3Homo sapiens (human)
protein bindingSphingosine 1-phosphate receptor 3Homo sapiens (human)
lipid bindingSphingosine 1-phosphate receptor 3Homo sapiens (human)
sphingosine-1-phosphate receptor activitySphingosine 1-phosphate receptor 3Homo sapiens (human)
G protein-coupled receptor activitySphingosine 1-phosphate receptor 3Homo sapiens (human)
protein bindingSphingosine 1-phosphate receptor 5Homo sapiens (human)
sphingosine-1-phosphate receptor activitySphingosine 1-phosphate receptor 5Homo sapiens (human)
G protein-coupled receptor activitySphingosine 1-phosphate receptor 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
mitochondrionSphingosine 1-phosphate receptor 4Homo sapiens (human)
plasma membraneSphingosine 1-phosphate receptor 4Homo sapiens (human)
plasma membraneSphingosine 1-phosphate receptor 4Homo sapiens (human)
cytoplasmSphingosine 1-phosphate receptor 4Homo sapiens (human)
nucleoplasmSphingosine 1-phosphate receptor 1Homo sapiens (human)
endosomeSphingosine 1-phosphate receptor 1Homo sapiens (human)
plasma membraneSphingosine 1-phosphate receptor 1Homo sapiens (human)
external side of plasma membraneSphingosine 1-phosphate receptor 1Homo sapiens (human)
intracellular membrane-bounded organelleSphingosine 1-phosphate receptor 1Homo sapiens (human)
membrane raftSphingosine 1-phosphate receptor 1Homo sapiens (human)
plasma membraneSphingosine 1-phosphate receptor 1Homo sapiens (human)
cytoplasmSphingosine 1-phosphate receptor 1Homo sapiens (human)
plasma membraneSphingosine 1-phosphate receptor 3Homo sapiens (human)
cytoplasmSphingosine 1-phosphate receptor 3Homo sapiens (human)
plasma membraneSphingosine 1-phosphate receptor 3Homo sapiens (human)
plasma membraneSphingosine 1-phosphate receptor 5Homo sapiens (human)
cytoplasmSphingosine 1-phosphate receptor 5Homo sapiens (human)
plasma membraneSphingosine 1-phosphate receptor 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID284817Efficacy at human S1P4 receptor expressed in HEK293T cells relative to S1P2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.
AID284818Efficacy at human S1P5 receptor expressed in HEK293T cells relative to S1P2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.
AID284814Efficacy at human S1P1 receptor expressed in HEK293T cells relative to S1P2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.
AID284813Activity at human S1P5 receptor expressed in HEK293T cells by [35S]GTP-gamma-S binding assay2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.
AID284815Efficacy at human S1P2 receptor expressed in HEK293T cells relative to S1P2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.
AID284812Activity at human S1P4 receptor expressed in HEK293T cells by [35S]GTP-gamma-S binding assay2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.
AID284816Efficacy at human S1P3 receptor expressed in HEK293T cells relative to S1P2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.
AID284811Activity at human S1P3 receptor expressed in HEK293T cells by [35S]GTP-gamma-S binding assay2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.
AID284809Activity at human S1P1 receptor expressed in HEK293T cells by [35S]GTP-gamma-S binding assay2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.
AID284810Activity at human S1P2 receptor expressed in HEK293T cells by [35S]GTP-gamma-S binding assay2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.
AID1346205Human S1P3 receptor (Lysophospholipid (S1P) receptors)2005The Journal of biological chemistry, Mar-18, Volume: 280, Issue:11
Sphingosine 1-phosphate analogs as receptor antagonists.
AID1346170Human S1P1 receptor (Lysophospholipid (S1P) receptors)2005The Journal of biological chemistry, Mar-18, Volume: 280, Issue:11
Sphingosine 1-phosphate analogs as receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (16.67)29.6817
2010's9 (75.00)24.3611
2020's1 (8.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.54

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 Index19.54 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index5.16 (4.65)
Search Engine Demand Index13.88 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.54)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]