1-palmitoyl-2-acetyl-sn-glycero-3-phosphocholine profile

1-Palmitoyl-2-acetyl-sn-glycero-3-phosphocholine (PAPC) is a synthetic phospholipid, which is a type of lipid molecule that contains a phosphate group.

Here's a breakdown of its components:

* **1-Palmitoyl:** Indicates a palmitic acid molecule attached to the first carbon of the glycerol backbone. Palmitic acid is a saturated fatty acid.
* **2-Acetyl:** Indicates an acetyl group (CH3CO-) attached to the second carbon of the glycerol backbone.
* **sn-Glycero-3-Phosphocholine:** This refers to the glycerol backbone with a phosphocholine group attached to the third carbon.

**Why is PAPC important for research?**

PAPC is used as a model system to study the properties of biological membranes and phospholipids. It plays a crucial role in research in several areas:

* **Membrane Structure and Dynamics:** PAPC helps researchers understand how phospholipids interact to form membranes, their fluidity, and how they respond to changes in the environment. This knowledge is crucial for understanding how cells function and communicate.
* **Drug Delivery and Targeting:** PAPC can be used to create liposomes, which are tiny spherical vesicles that encapsulate drugs. These liposomes can target specific cells or tissues, improving drug delivery and minimizing side effects.
* **Lipid Metabolism and Signaling:** PAPC is involved in various lipid metabolic pathways and cell signaling processes. Researchers use PAPC to study these processes and explore potential therapeutic targets for treating diseases.
* **Studying Membrane Protein Function:** PAPC provides a controlled environment to study the behavior of membrane proteins. Researchers can use PAPC to investigate how proteins interact with membranes and how they function in different cellular environments.

**Overall, PAPC is a valuable tool for researchers investigating various aspects of cell biology, membrane properties, and drug delivery. It offers a simple yet powerful model system to gain valuable insights into complex biological phenomena.**

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

1-palmitoyl-2-acetyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine in which the two acyl substituents at positions 1 and 2 are specified as palmitoyl and acetyl 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]

ID Source	ID
PubMed CID	16759367
CHEMBL ID	1335151
CHEBI ID	75219
SCHEMBL ID	434281
MeSH ID	M0126866

Synonym
1-palmitoyl-2-acetyl-sn-glycero-3-phosphorylcholine
1-palmitoyl-2-acetyl-sn-glycero-3-phosphocholine
pc(16:0/2:0)
1-o-palmitoyl-2-o-acetyl-sn-glyceryl-3-phosphorylcholine
1-hexadecanoyl-2-acetyl-sn-glycero-3-phosphocholine
LMGP01010612 ,
NCGC00161385-02
NCGC00161385-01
NCGC00161385-03
HMS1989E13
BML3-F04
HMS1361E13
HMS1791E13
CHEBI:75219 ,
1-palmitoyl-2-acetyl-sn-phosphatidylcholine
(2r)-2-acetoxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
(2r)-2-acetoxy-3-(palmitoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
SCHEMBL434281
CHEMBL1335151
79512-78-0
HMS3402E13
3,5,9-trioxa-4-phosphapentacosan-1-aminium, 7-(acetyloxy)-4-hydroxy-n,n,n-trimethyl-10-oxo-, inner salt, 4-oxide, (r)-
16:0-02:0 pc, 1-palmitoyl-2-acetyl-sn-glycero-3-phosphocholine, chloroform
Q27145169
3,5,9-trioxa-4-phosphapentacosan-1-aminium,7-(acetyloxy)-4-hydroxy-n,n,n-trimethyl-10-oxo-,inner salt,4-oxide,(7r)-
[(2r)-2-acetyloxy-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
3,5,9-trioxa-4-phosphapentacosan-1-aminium, 7-(acetyloxy)-4-hydroxy-n,n,n-trimethyl-10-oxo-, inner salt, 4-oxide, (7r)-
DTXSID701105288

Role	Description
platelet-activating factor receptor agonist	An agonist that binds to and activates platelet-activating factor receptors.
[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]

Class	Description
1,2-diacyl-sn-glycero-3-phosphocholine	The 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]

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, Cruzipain	Trypanosoma cruzi	Potency	19.9526	0.0020	14.6779	39.8107	AID1476
Microtubule-associated protein tau	Homo sapiens (human)	Potency	0.3981	0.1800	13.5574	39.8107	AID1468
regulator of G-protein signaling 4	Homo sapiens (human)	Potency	23.7781	0.5318	15.4358	37.6858	AID504845
euchromatic histone-lysine N-methyltransferase 2	Homo sapiens (human)	Potency	0.6310	0.0355	20.9770	89.1251	AID504332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID1347154	Primary screen GU AMC qHTS for Zika virus inhibitors	2020	Proceedings 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.
AID1508630	Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay	2021	Cell reports, 04-27, Volume: 35, Issue:4	A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID588519	A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities	2011	Antiviral research, Sep, Volume: 91, Issue:3	High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299	A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis	2010	Bioorganic & 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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (9.09)	18.7374
1990's	4 (36.36)	18.2507
2000's	2 (18.18)	29.6817
2010's	2 (18.18)	24.3611
2020's	2 (18.18)	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	11 (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
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2	1	alkyl hydroperoxide	antibacterial agent; oxidising agent
glycerylphosphorylcholine Glycerylphosphorylcholine: A component of PHOSPHATIDYLCHOLINES or LECITHINS, in which the two hydroxy groups of GLYCEROL are esterified with fatty acids. (From Stedman, 26th ed)	2.69	3	glycerophosphocholine
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2	1	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	1.96	1	D-glucopyranose	epitope; mouse metabolite
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.	3.24	6	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
formylmethionyl-leucyl-phenylalanine methyl ester [no description available]	2	1	peptide
1-o-hexadecyl-2-n-methylcarbamol -sn-glycerol-3-phosphocholine 1-O-hexadecyl-2-N-methylcarbamol -sn-glycerol-3-phosphocholine: PAF analog found in rabbit cornea; induces collagenase expression in corneal epithelial cells	1.99	1
palmitoyl-palmityl-lecithin ether palmitoyl-palmityl-lecithin ether: inhibitor of phospholipase A2; structure given in second source. 1-hexadecanoyl-2-hexadecyl-sn-glycero-3-phosphocholine : A 1-acyl-2-alkyl-sn-glycero-3-phosphocholine in which the acyl and alkyl groups at positions 1 and 2 are specified as hexadecanoyl and hexadecyl respectively.	1.99	1	1-acyl-2-alkyl-sn-glycero-3-phosphocholine; phosphatidylcholine O-32:0	Papio hamadryas metabolite
n-formylmethionine leucyl-phenylalanine N-Formylmethionine Leucyl-Phenylalanine: A formylated tripeptide originally isolated from bacterial filtrates that is positively chemotactic to polymorphonuclear leucocytes, and causes them to release lysosomal enzymes and become metabolically activated.. N-formyl-L-methionyl-L-leucyl-L-phenylalanine : A tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor.	2	1	tripeptide
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.	1.96	1	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
1-o-hexadecyl-2-arachidonyl-sn-glycero-3-phosphocholine 1-O-hexadecyl-2-arachidonyl-sn-glycero-3-phosphocholine: RN given refers to (all-Z)-isomer	1.96	1
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	2.68	3	benzoxazole
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	3.37	7	1,2-diacyl-sn-glycero-3-phosphocholine

Condition	Relationship Strength	Studies
Encephalitis, Polio [description not available]	2.06	1
Poliomyelitis An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)	2.06	1
Congenital Zika Syndrome [description not available]	2.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.25	1
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.25	1
Bleb [description not available]	1.99	1
Innate Inflammatory Response [description not available]	1.99	1
Pemphigoid [description not available]	1.99	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.	1.99	1
Pemphigoid, Bullous A chronic and relatively benign subepidermal blistering disease usually of the elderly and without histopathologic acantholysis.	1.99	1
Granulocytic Leukemia [description not available]	2	1
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	2	1

1-palmitoyl-2-acetyl-sn-glycero-3-phosphocholine

Description

Cross-References

Synonyms (28)

Roles (1)

Drug Classes (1)

Protein Targets (4)

Potency Measurements

Bioassays (4)

Research

Studies (11)

Study Types