Compounds > 1,2-diarachidonoyl-glycero-3-phosphocholine
Page last updated: 2024-12-11

1,2-diarachidonoyl-glycero-3-phosphocholine

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

Description

## 1,2-Diarachidonoyl-glycero-3-phosphocholine (1,2-Di-AA-GPC): The Basics

1,2-Diarachidonoyl-glycero-3-phosphocholine (1,2-Di-AA-GPC) is a specific type of **phospholipid**, a crucial component of cell membranes. It is characterized by:

* **Glycerol backbone:** This forms the core of the molecule.
* **Two arachidonic acid (AA) molecules:** These are fatty acids attached to the glycerol backbone at positions 1 and 2. Arachidonic acid is a polyunsaturated fatty acid known for its role in inflammation and cell signaling.
* **Phosphocholine head group:** This is attached to the glycerol backbone at position 3. It is hydrophilic (water-loving) and contributes to the overall structure and function of cell membranes.

## Importance in Research

1,2-Di-AA-GPC is gaining increasing attention in research due to its potential roles in:

**1. Cell Signaling and Inflammation:**

* **Precursor to pro-inflammatory mediators:** 1,2-Di-AA-GPC can be broken down by enzymes called phospholipases to release arachidonic acid. This released AA then serves as a precursor for the production of potent pro-inflammatory mediators like prostaglandins, leukotrienes, and thromboxanes.
* **Regulation of inflammation:** Studies suggest that 1,2-Di-AA-GPC might play a role in modulating inflammatory responses by impacting the activity of specific enzymes involved in the synthesis of these mediators.

**2. Neurological Disorders:**

* **Potential target for Alzheimer's disease:** Research indicates that 1,2-Di-AA-GPC may be involved in the pathogenesis of Alzheimer's disease. It has been shown to be altered in the brains of Alzheimer's patients, suggesting a potential connection to amyloid-beta aggregation and neuronal dysfunction.
* **Neuroprotection:** Some studies suggest that 1,2-Di-AA-GPC might exhibit neuroprotective effects, potentially by influencing neuronal signaling and membrane integrity.

**3. Cancer:**

* **Role in cancer development:** 1,2-Di-AA-GPC has been linked to cancer cell growth and proliferation, particularly in prostate cancer and breast cancer.
* **Potential therapeutic target:** Targeting the metabolism of 1,2-Di-AA-GPC or its related pathways might offer new strategies for cancer prevention and treatment.

**4. Other areas of research:**

* **Cardiovascular health:** 1,2-Di-AA-GPC is being investigated for its potential role in regulating blood pressure and platelet aggregation.
* **Immune system:** Research is ongoing to understand the role of 1,2-Di-AA-GPC in immune responses, particularly in the context of autoimmunity.

## Future Directions

The research on 1,2-Di-AA-GPC is still in its early stages, but it holds significant promise for furthering our understanding of cellular processes, disease mechanisms, and potential therapeutic targets. Further investigations are necessary to elucidate its precise roles in different biological systems and to develop safe and effective interventions based on its properties.

1,2-diarachidonoyl-glycero-3-phosphocholine: RN given refers to (all-Z)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,2-di-O-arachidonoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine in which the phosphatidyl acyl groups at positions 1 and 2 are both arachidonoyl. [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 CID24779076
CHEBI ID60657
SCHEMBL ID235399
MeSH IDM0130658

Synonyms (37)

Synonym
dapc
1,2-diarachidonylphosphatidylcholine
l-diarachidonoyl lecithin
1,2-di-(5z,8z,11z,14z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
LMGP01011052
pc(20:4/20:4)
1,2-diarachidonyl-l-alpha-glycerophosphorylcholine
arachidonin, 1,2-di, dihydrogen phosphate, monoester with choline hydroxide, inner salt, l-
diarachidonoylphosphatidylcholine
choline, hydroxide, dihydrogen phosphate, inner salt, ester with 1,2-diarachidonin, l-
diarachidonyl phosphatidylcholine
pc(20:4(5z,8z,11z,14z)/20:4(5z,8z,11z,14z))
diarachidonyl lecithin
1,2-diarachidonoyl-sn-glycero-3-phosphocholine
1,2-di-o-arachidonoyl-sn-glycero-3-phosphocholine
(7r,14z,17z,20z,23z)-4-hydroxy-7-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]-n,n,n-trimethyl-10-oxo-3,5,9-trioxa-4-phosphanonacosa-14,17,20,23-tetraen-1-aminium 4-oxide
CHEBI:60657 ,
1,2-diarachidonoyl-glycero-3-phosphocholine
1,2-diarachidyl-3-phosphatidylcholine
17688-29-8
SCHEMBL235399
20:4 (cis) pc
LZLVZIFMYXDKCN-QJWFYWCHSA-N
3,5,9-trioxa-4-phosphanonacosa-14,17,20,23-tetraen-1-aminium, 4-hydroxy-n,n,n-trimethyl-10-oxo-7-[(1-oxo-5,8,11,14-eicosatetraenyl)oxy]-, inner salt, 4-oxide, [r-(all-z)]-
pc(20:4n6/20:4n6)
phosphatidylcholine(20:4n6/20:4n6)
gpcho(20:4w6/20:4w6)
gpcho(20:4n6/20:4n6)
phosphatidylcholine(20:4w6/20:4w6)
pc(20:4w6/20:4w6)
1,2-diarachidonoyl-rac-glycero-3-phosphocholine
(2-{[(2r)-2,3-bis[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Q27104877
l-a-lecithin-diarachidonoyl
diarachidonoyl phosphatidylcholine
DTXSID801297385
PD053621
[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-diacyl-sn-glycero-3-phosphocholineThe conjugate base of a 1,2-diacyl-sn-glycero-3-phosphocholine compound formed by deprotonation of the phosphate OH group.
[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 (5)

PathwayProteinsCompounds
Lysolipid Incorporation into ER PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))1023
Lysolipid incorporation into Mitochondria PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))514
Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))620
Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))516
Phosphatidylcholine/Phosphatidylethanolamine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) | PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))617

Research

Studies (28)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (25.00)18.7374
1990's5 (17.86)18.2507
2000's6 (21.43)29.6817
2010's10 (35.71)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other28 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
betaine
glycine betaine : The amino acid betaine derived from glycine.		210amino-acid betaine;
glycine derivative		fundamental metabolite
choline
[no description available]		210cholinesallergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter;
nutrient;
plant metabolite;
Saccharomyces cerevisiae 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.		2.1110phosphocholinesallergen;
epitope;
hapten;
human metabolite;
mouse metabolite
miltefosine
miltefosine: hexadecyl phosphocholine derivative of cisplatin; did not substantially activate HIV long terminal repeat; less toxic than cisplatin. miltefosine : A phospholipid that is the hexadecyl monoester of phosphocholine.		2.1110phosphocholines;
phospholipid		anti-inflammatory agent;
anticoronaviral agent;
antifungal agent;
antineoplastic agent;
antiprotozoal drug;
apoptosis inducer;
immunomodulator;
protein kinase inhibitor
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.		3.5280
2-naphthylamine
2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.		210naphthylaminecarcinogenic agent
dithiothreitol
1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.		1.97101,4-dimercaptobutane-2,3-diol;
butanediols;
dithiol;
glycol;
thiol		chelator;
human metabolite;
reducing agent
fluorides
[no description available]		2.0310halide anion;
monoatomic fluorine
bw-755c
4,5-Dihydro-1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-amine: A dual inhibitor of both cyclooxygenase and lipoxygenase pathways. It exerts an anti-inflammatory effect by inhibiting the formation of prostaglandins and leukotrienes. The drug also enhances pulmonary hypoxic vasoconstriction and has a protective effect after myocardial ischemia.		1.9710
1,2-dipalmitoyl-3-phosphatidylethanolamine
1,2-dipalmitoyl-3-phosphatidylethanolamine: RN given refers to parent cpd without isomeric designation		210
1,2-distearoyllecithin
[no description available]		3.0850
lissamine rhodamine b
lissamine rhodamine B: RN given refers to parent cpd; Lissamine Rhodamine B refers to Na salt		210
laurdan
laurdan: RN from CA Index Guide		210
1-hexadecyl-2-acetyl-glycero-3-phosphocholine
Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.		1.97102-acetyl-1-alkyl-sn-glycero-3-phosphocholineantihypertensive agent;
beta-adrenergic antagonist;
bronchoconstrictor agent;
hematologic agent;
vasodilator agent
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.		3.0850icosa-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
1,2-dilauroylphosphatidylcholine
1,2-dilauroylphosphatidylcholine: RN given refers to cpd without isomeric designation. 1,2-dilauroyl-sn-glycero-3-phosphocholine(1+) : A A 1,2-diacyl-sn-glycero-3-phosphocholine(1+) that is the dilauroyl diester of phosphatidiylcholine.		2.44201,2-diacyl-sn-glycero-3-phosphocholine(1+)
sphingosine
sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.		2.1110sphing-4-eninehuman metabolite;
mouse metabolite
1,2-oleoylphosphatidylcholine
1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.		2.1110phosphatidylcholine(1+)
dimyristoylphosphatidylcholine
1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).		2.91401,2-diacyl-sn-glycero-3-phosphocholine;
phosphatidylcholine 28:0;
tetradecanoate ester		antigen;
mouse metabolite
phosphorus
Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.		1.9810monoatomic phosphorus;
nonmetal atom;
pnictogen		macronutrient
1-palmitoyl-2-oleoylphosphatidylcholine
1-palmitoyl-2-oleoylphosphatidylcholine: RN given refers to (Z)-isomer		2.5120
1,2-dioleoyloxy-3-(trimethylammonium)propane
1,2-dioleoyloxy-3-(trimethylammonium)propane: fluorescent probe for phospholipids; RN & structure given in first source		2.1110
1,2-linoleoylphosphatidylcholine
1,2-linoleoylphosphatidylcholine: used for premature induction of labor in rabbits; RN given refers to (all Z)-isomer		2.730
1,2-diarachidonoyl-glycero-3-phosphoethanolamine
1,2-diarachidonoyl-glycero-3-phosphoethanolamine: RN given refers to (R-(all-Z))-isomer		2.3720
melitten
Melitten: Basic polypeptide from the venom of the honey bee (Apis mellifera). It contains 26 amino acids, has cytolytic properties, causes contracture of muscle, releases histamine, and disrupts surface tension, probably due to lysis of cell and mitochondrial membranes.		1.9810
gramicidin a
Gramicidin: A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.		2.110
phosphatidylcholines
Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.		4.682801,2-diacyl-sn-glycero-3-phosphocholine
glycolipids
[no description available]		1.9710
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.0310
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.		02.0310
Kahler Disease
[description not available]		0210
Multiple Myeloma
A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.		0210
Acute Promyelocytic Leukemia
[description not available]		01.9810
Leukemia, Promyelocytic, Acute
An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.		01.9810
Blood Clot
[description not available]		01.9710
Thrombosis
Formation and development of a thrombus or blood clot in the blood vessel.		01.9710
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		01.9710