Page last updated: 2024-12-11

1-stearoyl-2-arachidonoylglycerol

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

Description

1-stearoyl-2-arachidonoylglycerol (SAG) is a **monoacylglycerol** (MAG) lipid that plays a significant role in various biological processes.

**Here's a breakdown of its structure and importance in research:**

**Structure:**

* SAG consists of a glycerol backbone attached to:
* **Stearic acid** (a saturated fatty acid) at the sn-1 position.
* **Arachidonic acid** (an omega-6 polyunsaturated fatty acid) at the sn-2 position.

**Importance in Research:**

1. **Signaling Molecule:** SAG acts as a signaling molecule in the endocannabinoid system. It binds to the **peroxisome proliferator-activated receptor alpha (PPARĪ±)** and **G protein-coupled receptor 119 (GPR119)**, which are implicated in:
* **Metabolic regulation:** SAG plays a role in controlling glucose homeostasis, lipid metabolism, and insulin sensitivity.
* **Inflammation:** SAG has anti-inflammatory effects, possibly through modulation of PPARĪ± signaling.
* **Neuroprotection:** SAG has shown potential in protecting against neuronal damage in various neurological conditions.

2. **Cell Signaling:** SAG is involved in various intracellular signaling pathways. For example, it can:
* Activate **protein kinase C (PKC)**, a key enzyme in cell signaling.
* Modulate **calcium signaling**, influencing cellular processes.
* Influence **gene expression** by affecting transcription factors.

3. **Therapeutic Potential:** Research on SAG is exploring its therapeutic potential in various conditions, including:
* **Metabolic diseases:** Type 2 diabetes, obesity, and dyslipidemia.
* **Neurological disorders:** Alzheimer's disease, Parkinson's disease, and stroke.
* **Inflammatory diseases:** Arthritis, Crohn's disease, and asthma.
* **Cancer:** SAG shows anti-proliferative effects in some cancer cells.

**Research Focus:**

Current research focuses on understanding the precise mechanisms by which SAG exerts its effects and exploring its therapeutic potential. This includes:

* **Developing synthetic analogs of SAG** with enhanced potency and selectivity for specific receptors.
* **Investigating the role of SAG in different tissues and organs**.
* **Conducting preclinical and clinical trials** to assess its efficacy and safety in human patients.

**Overall, 1-stearoyl-2-arachidonoylglycerol (SAG) is a promising molecule with potential applications in various fields, including medicine, pharmacology, and nutrition.**

## 1-Stearoyl-2-arachidonoylglycerol (SAG)

**What is it?**

1-stearoyl-2-arachidonoylglycerol (SAG) is a **monoacylglycerol** (MAG), which is a type of lipid molecule containing a glycerol backbone linked to one fatty acid. In the case of SAG:

* The **sn-1 position** is linked to **stearic acid**, a saturated fatty acid with 18 carbons.
* The **sn-2 position** is linked to **arachidonic acid**, a polyunsaturated fatty acid with 20 carbons.

**Why is it important for research?**

SAG is a potent **endocannabinoid** that plays a significant role in various physiological processes and is a subject of intense research due to its potential therapeutic implications. Here's why:

* **Endocannabinoid System (ECS) Modulation:** SAG is an **agonist** of the **cannabinoid receptor 2 (CB2)**, which is primarily expressed in the immune system and plays a crucial role in regulating inflammation, pain, and immune responses.
* **Anti-Inflammatory Effects:** SAG's activation of CB2 leads to anti-inflammatory effects by suppressing the release of pro-inflammatory cytokines and chemokines. This makes SAG a potential therapeutic target for inflammatory conditions like rheumatoid arthritis, inflammatory bowel disease, and multiple sclerosis.
* **Analgesic Effects:** SAG exhibits analgesic properties, potentially acting through both CB2 and other mechanisms. This suggests its potential in treating pain associated with different conditions.
* **Neuroprotective Effects:** SAG can protect neurons against damage and death, potentially by reducing oxidative stress and inflammation. This makes it a promising candidate for treating neurodegenerative diseases such as Alzheimer's and Parkinson's.
* **Metabolic Effects:** SAG has been shown to influence metabolism by regulating glucose homeostasis and insulin sensitivity, potentially contributing to the management of diabetes and obesity.
* **Anti-Cancer Effects:** Recent studies suggest that SAG may have anti-cancer properties, inhibiting tumor growth and promoting apoptosis.

**Current Research:**

Researchers are actively investigating the therapeutic potential of SAG in various conditions, including:

* **Inflammation:** Rheumatoid arthritis, inflammatory bowel disease, multiple sclerosis
* **Pain:** Chronic pain, neuropathic pain
* **Neurodegenerative diseases:** Alzheimer's disease, Parkinson's disease
* **Metabolic disorders:** Diabetes, obesity
* **Cancer:** Different types of cancer

**Challenges and Future Directions:**

Despite its promising potential, research on SAG still faces some challenges:

* **Delivery:** SAG is susceptible to enzymatic degradation, limiting its oral bioavailability. Developing effective delivery systems is crucial for clinical application.
* **Specificity:** SAG activates CB2 but may also have off-target effects on other receptors. More research is needed to refine its selectivity and optimize its therapeutic window.
* **Clinical Trials:** While promising, SAG's clinical efficacy is still under investigation. Well-designed clinical trials are required to confirm its therapeutic potential and establish its safety profile.

Overall, 1-stearoyl-2-arachidonoylglycerol (SAG) is a fascinating molecule with significant implications for research and potential therapeutic applications. Its role in modulating the endocannabinoid system, combined with its anti-inflammatory, analgesic, neuroprotective, metabolic, and anti-cancer properties, makes it a promising candidate for developing novel treatments for various diseases. Further research is necessary to fully understand its mechanisms of action and optimize its therapeutic potential.

1-stearoyl-2-arachidonoylglycerol : A 1,2-diglyceride in which the acyl groups at positions 1 and 2 are specifed as stearoyl and arachidonoyl respectively. [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-2-arachidonoyl-sn-glycerol : A 1,2-diacyl-sn-glycerol in which the acyl groups at positions 1 and 2 are specifed as stearoyl and arachidonoyl respectively. [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 CID14345637
CHEBI ID83288
SCHEMBL ID1412343
MeSH IDM0204123
PubMed CID6438587
CHEBI ID75728
SCHEMBL ID1009384
MeSH IDM0204123

Synonyms (53)

Synonym
1-stearoyl-2-arachidonoyl-sn-glycerol, ~98%, suitable for stimulation of protein kinase c derived from liver cells, liquid
1-stearoyl-2-arachidonoylglycerol
CHEBI:83288
1-hydroxy-3-(octadecanoyloxy)propan-2-yl (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate
1-octadecanoyl-2-(5z,8z,11z,14z)-eicosatetraenoylglycerol
1-octadecanoyl-2-(5z,8z,11z,14z)-icosatetraenoylglycerol
SCHEMBL1412343
Q27156731
(1-hydroxy-3-octadecanoyloxypropan-2-yl) (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate
1-stearin-2-arachidonin-sn-glycerol
gtpl2437
dg(18:0_20:4)
dg(18:0/20:4/0:0)[iso2]
1-octadecanoyl-2-(5z,8z,11z,14z-eicosatetraenoyl)-sn-glycerol
LMGL02010111
dg(18:0/20:4(5z,8z,11z,14z)/0:0)[iso2]
IDI1_033877
BSPBIO_001407
1-stearoyl-2-arachidonoyl-sn-glycerol
NCGC00161335-01
NCGC00161335-02
NCGC00161335-03
65914-84-3
1-stearoyl-2-arachidonoyl-glycerol
HMS1989G09
BML2-F09
HMS1791G09
HMS1361G09
[(2s)-1-hydroxy-3-octadecanoyloxypropan-2-yl] (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate
(2s)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate
dag(18:0/20:4omega6)
dag(18:0/20:4)
(2s)-1-hydroxy-3-(stearoyloxy)propan-2-yl (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate
dg(18:0/20:4(5z,8z,11z,14z)/0:0)
CHEBI:75728
dg(18:0/20:4omega6)
dg(18:0/20:4(omega-6)/0:0)
diacylglycerol(18:0/20:4omega6)
diacylglycerol(18:0/20:4)
5,8,11,14-eicosatetraenoic acid, 1-(hydroxymethyl)-2-((1-oxooctadecyl)ethyl) ester, (s-(all-z))-
SCHEMBL1009384
HMS3402G09
AKOS027379145
dg(18:0/20:4w6)
dg(18:0/20:4n6)
dag(18:0/20:4w6)
diacylglycerol(18:0/20:4w6)
dag(18:0/20:4n6)
Q27088683
diacylglycerol(18:0/20:4n6)
HY-131897
DTXSID901286391
CS-0142415
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
1,2-diglyceride
1,2-diacyl-sn-glycerol
[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]

Pathways (30)

PathwayProteinsCompounds
Activation of PKC Through G Protein-Coupled Receptor46
Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))620
Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))516
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))514
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/18:0)514
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:0)515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:0)515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/24:0)515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/14:1(9Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:1(11Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:3(5Z,8Z,11Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/18:3(6Z,9Z,12Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/18:3(9Z,12Z,15Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/18:4(6Z,9Z,12Z,15Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))515
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:2(11Z,14Z))514
De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z))514
Phosphatidylcholine/Phosphatidylethanolamine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z)) | PE(18:0/20:4(5Z,8Z,11Z,14Z))617

Bioassays (6)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
AID1346590Human TRPC6 (Transient Receptor Potential channels)1999Nature, Jan-21, Volume: 397, Issue:6716
Direct activation of human TRPC6 and TRPC3 channels by diacylglycerol.
AID1346613Mouse TRPC2 (Transient Receptor Potential channels)2003Neuron, Oct-30, Volume: 40, Issue:3
A diacylglycerol-gated cation channel in vomeronasal neuron dendrites is impaired in TRPC2 mutant mice: mechanism of pheromone transduction.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's9 (33.33)18.2507
2000's9 (33.33)29.6817
2010's6 (22.22)24.3611
2020's3 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.85

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 Index12.85 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.85)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other21 (100.00%)84.16%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]