Page last updated: 2024-12-11

1-oleoyl-2-acetylglycerol

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

1-Oleoyl-2-acetylglycerol (OAG) is a synthetic lipid that plays a crucial role in research, primarily in the fields of **cell signaling and cancer biology**.

Here's a breakdown of its key features and importance:

**What it is:**

* **Structure:** OAG is a diglyceride, meaning it consists of a glycerol backbone with two fatty acid chains attached.
* **Components:** One fatty acid chain is oleic acid (an unsaturated fatty acid), and the other is acetic acid (a short-chain saturated fatty acid).
* **Synthesis:** It's synthesized in the lab and not found naturally in significant amounts.

**Why it's important in research:**

* **Mimics diacylglycerol (DAG):** OAG acts as a potent mimic of diacylglycerol (DAG), a natural signaling molecule involved in various cellular processes. DAG is produced by the breakdown of phospholipids and plays a role in activating protein kinase C (PKC), a key enzyme involved in cell growth, differentiation, and survival.
* **PKC activator:** OAG directly activates PKC, making it a valuable tool for studying the role of PKC in various cellular processes. This is important for understanding:
* **Cancer biology:** PKC is often overactive in cancer cells, contributing to their uncontrolled growth. OAG can be used to investigate PKC's role in cancer development and test the effectiveness of PKC inhibitors as potential cancer treatments.
* **Cell signaling:** PKC is involved in a wide range of cellular processes, including memory formation, inflammation, and insulin signaling. OAG allows researchers to study the intricate signaling pathways involving PKC and its downstream targets.
* **Other research applications:** OAG is also used to study:
* **Lipid metabolism:** Its effects on lipid metabolism can be studied, potentially leading to better understanding of obesity and metabolic disorders.
* **Neuroplasticity:** Its role in neuronal growth and plasticity is being investigated.

**Limitations:**

* **Non-physiological:** While OAG mimics DAG, it's not an exact replica. It's important to note that OAG's effects might not be entirely representative of natural DAG activity.
* **Specificity:** OAG can activate various PKC isoforms, making it difficult to study the specific roles of individual isoforms.

**Overall:**

1-Oleoyl-2-acetylglycerol (OAG) is a valuable research tool used to study the role of PKC in various cellular processes. Its ability to activate PKC, combined with its synthetic nature, provides researchers with a controlled way to investigate the intricate signaling pathways and potential therapeutic applications of PKC modulation.

Cross-References

ID SourceID
PubMed CID6437055
CHEMBL ID1591456
CHEBI ID188094
SCHEMBL ID1002909
MeSH IDM0115217

Synonyms (37)

Synonym
IDI1_033873
BSPBIO_001403
1-oleoyl-2-acetyl-sn-glycerol
NCGC00161334-01
NCGC00161334-02
NCGC00161334-03
1-o-octadecenoyl-2-o-acetylglycerol
1-oleoyl-2-acetyl-glycerol
86390-77-4
9-octadecenoic acid (z)-, 2-(acetyloxy)-3-hydroxypropyl ester, (s)-
1-oleyl-2-acetylglycerol
1-oleoyl-2-acetylglycerol
HMS1989G05
BML2-F08
HMS1361G05
HMS1791G05
CHEBI:188094
[(2s)-2-acetyloxy-3-hydroxypropyl] (z)-octadec-9-enoate
9-octadecenoic acid (9z)-, (2s)-2-(acetyloxy)-3-hydroxypropyl ester
2-acetyl-1-oleoyl-sn-glycerol
sn-1-oleoyl-2-acetylglycerol
SCHEMBL1002909
CHEMBL1591456
1-o-9z-octadecenoyl-2-o-acetyl-sn-glycerol
PWTCCMJTPHCGMS-YRBAHSOBSA-N
HMS3649G05
HMS3402G05
AKOS027257477
1-oleoyl-2-acetyl-sn-glycerol - cas 86390-77-4
sr-01000946570
SR-01000946570-1
1-olein-2-acetyl-sn-glycerol
HY-131648
CS-0138170
PD020881
(s)-2-acetoxy-3-hydroxypropyl oleate
BP-29900

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" Other protein kinase C activators also markedly enhanced O2- production in combination with hypotonicity, but not in the isotonic medium."( Stimulation of superoxide anion production in guinea pig polymorphonuclear leukocytes by hypotonic conditions in combination with protein kinase C activators.
Hiura, M; Ishibashi, S; Ohtsuka, T; Okamura, N; Ozawa, M; Takesue, H; Yamaguchi, M, 1991
)
0.28

Bioavailability

ExcerptReferenceRelevance
" Conversion of an isoquinoline amide to a naphthyridine amide markedly reduced clearance for the bicyclic piperidines, and improved oral bioavailability for this compound series, however TRPC3 and TRPC6 blocking activity was reduced substantially."( The discovery of potent blockers of the canonical transient receptor channels, TRPC3 and TRPC6, based on an anilino-thiazole pharmacophore.
Barton, L; Basilla, JB; Davenport, EA; Dodson, J; Fries, RE; Gillie, DJ; Guss, J; Holt, DA; Jensen, TC; Klein, M; Lozinskaya, IM; Manns, S; Marino, JP; McAtee, JJ; Morrow, DM; Negron, LK; Pritchard, C; Schnackenberg, CG; Terrell, LR; Washburn, DG; Waszkiewicz, A; Willette, RN; Xu, X, 2013
)
0.39

Dosage Studied

ExcerptRelevanceReference
" Similarly, dose-response curves for pepsinogen secretion and the increase in membrane-associated PKC activity induced by a membrane-permeant DAG (1-oleoyl-2-acetylglycerol) were superimposable."( Cellular distribution of gastric chief cell protein kinase C activity: differential effects of diacylglycerol, phorbol esters, carbachol, and cholecystokinin.
Raffaniello, RD; Raufman, JP, 1992
)
0.48
" The most effective inhibitory dosage with maximal carbachol (10(-5) M; 30."( Prostaglandin E analogue inhibition of pancreatic enzyme secretion.
Adrian, TE; Bilchik, AJ; Modlin, IM; Zucker, KA, 1989
)
0.28
" The OAG effect on testosterone production was inhibitory throughout the dose-response curve of 8-bromo-cAMP."( Effects of protein kinase C activation on cyclic AMP and testosterone production of rat Leydig cells in vitro.
Huhtaniemi, I; Nikula, H, 1989
)
0.28
" This decrease paralleled the time course and dose-response of the inhibition of cytocidal activity."( Tumor necrosis factor receptors and cytocidal activity are down-regulated by activators of protein kinase C.
Baglioni, C; Johnson, SE, 1988
)
0.27
" Protein kinase C activators increased the apparent maximum of the ionophoretic dose-response curve for glutamate-induced depolarization, without affecting the reversal potential and the voltage-dependent decay rate for the excitatory postsynaptic current (EPSC) under voltage-clamp conditions."( Activation of protein kinase C promotes glutamate-mediated transmission at the neuromuscular junction of the mealworm.
Yamamoto, D, 1988
)
0.27
" Furthermore, the magnitude of the translocation of protein kinase C from cytosol to plasma membrane corresponded to the physiologic IL 2 dose-response for IFN-gamma secretion."( Interleukin 2 induction of interferon-gamma mRNA synthesis.
Birchenall-Sparks, MC; Farrar, WL; Young, HB, 1986
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
1,2-diglyceride
[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 (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
phosphopantetheinyl transferaseBacillus subtilisPotency89.12510.141337.9142100.0000AID1490
regulator of G-protein signaling 4Homo sapiens (human)Potency4.22840.531815.435837.6858AID504845
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (616)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990259 (42.05)18.7374
1990's227 (36.85)18.2507
2000's106 (17.21)29.6817
2010's21 (3.41)24.3611
2020's3 (0.49)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 7.73

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 Index7.73 (24.57)
Research Supply Index6.44 (2.92)
Research Growth Index4.18 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (7.73)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (0.64%)6.00%
Case Studies1 (0.16%)4.05%
Observational0 (0.00%)0.25%
Other621 (99.20%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]