1-stearoyl-2-arachidonylphosphatidylcholine profile

## 1-Stearoyl-2-arachidonylphosphatidylcholine (SAPC)

**What it is:**

1-Stearoyl-2-arachidonylphosphatidylcholine (SAPC) is a type of **phospholipid**, specifically a **phosphatidylcholine**, which is a major component of cell membranes. It consists of:

* **Glycerol:** A 3-carbon molecule that forms the backbone of the lipid.
* **Two fatty acids:**
* **Stearic acid (C18:0):** A saturated fatty acid attached to the first carbon of glycerol.
* **Arachidonic acid (C20:4):** An unsaturated fatty acid attached to the second carbon of glycerol.
* **Phosphate group:** Attached to the third carbon of glycerol.
* **Choline:** A nitrogenous base attached to the phosphate group.

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

SAPC is a valuable tool in research for several reasons:

**1. Membrane Studies:**

* **Model membrane formation:** SAPC is often used to create **liposomes**, which are artificial vesicles that mimic cell membranes. These liposomes allow researchers to study membrane properties, such as fluidity, permeability, and protein interactions in a controlled environment.
* **Investigating lipid-protein interactions:** SAPC can be used to investigate how proteins interact with specific lipids in the cell membrane. This is particularly important for understanding the function of membrane proteins involved in signal transduction, transport, and other cellular processes.

**2. Signal Transduction and Inflammation:**

* **Arachidonic acid release:** SAPC contains arachidonic acid, a precursor to a variety of signaling molecules involved in inflammation, pain, and fever. Researchers can use SAPC to study the release and metabolism of arachidonic acid in response to various stimuli.
* **Studying the effects of phospholipases:** Phospholipases are enzymes that break down phospholipids, including SAPC. Researchers use SAPC to study the activity of phospholipases and their roles in cell signaling and disease processes.

**3. Drug Delivery and Nanomedicine:**

* **Drug encapsulation:** Liposomes made from SAPC can be used to encapsulate drugs and deliver them to specific cells or tissues. This approach is promising for developing new targeted drug therapies.
* **Nanoparticle fabrication:** SAPC can be incorporated into nanoparticles for drug delivery, diagnostics, and other biomedical applications.

**In conclusion**, 1-stearoyl-2-arachidonylphosphatidylcholine (SAPC) is a valuable tool for researchers studying various aspects of cell membranes, signal transduction, and drug delivery. Its unique properties, including its ability to form stable liposomes and its content of the important signaling molecule arachidonic acid, make it a crucial reagent in various research areas.

1-stearoyl-2-arachidonylphosphatidylcholine: RN given refers to (all-Z)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	6441413
MeSH ID	M0128300

Synonym
1-stearoyl-2-arachidonylphosphatidylcholine
[2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyl]oxy-3-octadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
1-stearoyl-2-arachidonylcholine phosphoglyceride
3,5,8-trioxa-4-phosphaoctacosa-13,16,19,22-tetraen-1-aminium, 4-hydroxy-n,n,n-trimethyl-9-oxo-7-(((1-oxooctadecyl)oxy)methyl)-, inner salt, 4-oxide, (all-z)-
1-stearoyl-2-arachidonoyl-sn-glycero-phosphocholine
alpha-stearoyl-beta-arachidonyl-l-phosphatidylcholine
st-ar-phosphatidylcholine
18892-74-5
stearoylarachidonylphosphatidylcholine

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (12.50)	18.7374
1990's	8 (50.00)	18.2507
2000's	3 (18.75)	29.6817
2010's	3 (18.75)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	17 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.41	2	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
phosphorylcholine Phosphorylcholine: Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.. phosphocholine : The phosphate of choline; and the parent compound of the phosphocholine family.	2.01	1	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	1.96	1	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	1.96	1	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.15	1	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	1.98	1
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	1.99	1	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	1.98	1	amino sulfonic acid; bile acid taurine conjugate	human metabolite
pregnenolone [no description available]	1.96	1	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
dehydroepiandrosterone sulfate Dehydroepiandrosterone Sulfate: The circulating form of a major C19 steroid produced primarily by the ADRENAL CORTEX. DHEA sulfate serves as a precursor for TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE.. dehydroepiandrosterone sulfate : A steroid sulfate that is the 3-sulfooxy derivative of dehydroepiandrosterone.	1.96	1	17-oxo steroid; steroid sulfate	EC 2.7.1.33 (pantothenate kinase) inhibitor; human metabolite; mouse metabolite
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.92	4	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
cholesteryl sulfate cholesteryl sulfate: component of human seminal plasma & spermatozoa; RN given refers to (3beta)-isomer. cholesterol sulfate : A steroid sulfate that is cholesterol substituted by a sulfoxy group at position 3.	1.96	1	steroid sulfate	human metabolite
1,2-dipalmitoyl-3-phosphatidylethanolamine 1,2-dipalmitoyl-3-phosphatidylethanolamine: RN given refers to parent cpd without isomeric designation	1.98	1
glycerophosphoinositol 4,5-bisphosphate glycerophosphoinositol 4,5-bisphosphate: do not confuse with phosphatidylinositols which have fatty acids esterified at the C-1 and C-2 hydroxyl groups of glycerol	1.99	1
taurochenodeoxycholic acid Taurochenodeoxycholic Acid: A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic.. taurochenodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurochenodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. taurochenodeoxycholic acid : A bile acid taurine conjugate of chenodeoxycholic acid.	1.98	1	bile acid taurine conjugate	human metabolite; mouse metabolite
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	3.09	5	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	1.98	1	diphosphate ion
glyceryl 2-arachidonate glyceryl 2-arachidonate: binds to cannabinoid receptors; structure in first source. 2-arachidonoylglycerol : An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.	2.05	1	2-acylglycerol 20:4; endocannabinoid	human metabolite
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	1.98	1	1-O-acyl-sn-glycero-3-phosphocholine
1-palmitoyl-2-oleoylphosphatidylcholine 1-palmitoyl-2-oleoylphosphatidylcholine: RN given refers to (Z)-isomer	2.4	2
1-palmitoyl-2-linoleoylphosphatidylcholine [no description available]	2.68	3
ursodoxicoltaurine tauroursodeoxycholate : An organosulfonate oxoanion that is the conjugate base of tauroursodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. tauroursodeoxycholic acid : A bile acid taurine conjugate derived from ursoodeoxycholic acid.	1.98	1	bile acid taurine conjugate	anti-inflammatory agent; apoptosis inhibitor; bone density conservation agent; cardioprotective agent; human metabolite; neuroprotective agent
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	2.69	3	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	4.13	16	1,2-diacyl-sn-glycero-3-phosphocholine
phosphatidylcholines 1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine: RN given refers to (Z)-isomer. 1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine : A phosphatidylcholine 36:1 in which the phosphatidyl acyl groups at positions 1 and 2 are stearoyl and oleoyl respectively.	2.41	2	1-acyl-2-oleoyl-sn-glycero-3-phosphocholine betaine; 1-octadecanoyl-2-octadecenoyl-sn-glycero-3-phosphocholine

Condition	Relationship Strength	Studies
Innate Inflammatory Response [description not available]	2.15	1
Infections, Picornaviridae [description not available]	2.15	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.15	1
Extravascular Hemolysis [description not available]	2.05	1
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.05	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.67	3
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	1.98	1

1-stearoyl-2-arachidonylphosphatidylcholine

Description

Cross-References

Synonyms (9)

Research

Studies (16)

Market Indicators

Research Demand Index: 11.89

Study Types