1-o-hexadecyl-2-n-methylcarbamylphosphatidylcholine profile

**1-O-hexadecyl-2-N-methylcarbamylphosphatidylcholine (16:0-MPPC)** is a synthetic phospholipid analog that is widely used in research.

**Structure and Properties:**

- **16:0-MPPC** has a saturated acyl chain at the sn-1 position (hexadecanoyl, 16 carbons) and a N-methylcarbamoyl group at the sn-2 position.
- The phosphate group is linked to choline, forming a phosphatidylcholine headgroup.
- It is a liquid at room temperature and is soluble in organic solvents.

**Importance in Research:**

**1. Model Membrane Systems:**

- **16:0-MPPC** is a commonly used component in model membrane systems, such as liposomes and bilayers.
- Its structural similarity to natural phospholipids allows it to mimic the properties of biological membranes, providing a controlled environment for studying membrane-related processes.

**2. Membrane Dynamics and Interactions:**

- **16:0-MPPC** is used to study the dynamics of lipid bilayers, including phase transitions, fluidity, and lateral diffusion.
- It can also be used to investigate the interactions of proteins, drugs, and other molecules with membranes.

**3. Drug Delivery and Targeting:**

- **16:0-MPPC** is a potential carrier for drug delivery systems.
- Its ability to form liposomes and its membrane-interacting properties can enhance drug encapsulation, stability, and targeting.

**4. Cell Signaling and Receptor Activation:**

- **16:0-MPPC** can influence cell signaling pathways by modulating the activity of membrane-bound receptors.
- It can also be used to study the role of lipid rafts in cellular processes.

**5. Biophysical Studies:**

- **16:0-MPPC** is a valuable tool for biophysical studies, such as X-ray diffraction, neutron scattering, and nuclear magnetic resonance spectroscopy.
- These techniques provide insights into the structure and dynamics of lipid bilayers at the molecular level.

**Conclusion:**

**16:0-MPPC** is a versatile and widely used phospholipid analog in research. Its ability to mimic biological membranes and its unique properties make it a valuable tool for studying membrane-related processes, drug delivery, and cell signaling.

1-O-hexadecyl-2-N-methylcarbamylphosphatidylcholine: biologically active analog of PAF; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	2495
MeSH ID	M0151512

Synonym
111057-91-1
methylcarbamyl-paf
1-o-hexadecyl-2-n-methylcarbamyl-glycerophosphocholine
n-carbamyl-paf
1-o-hexadecyl-2-n-methylcarbamylphosphatidylcholine
carbamyl-platelet-activating factor
1-hmc-gpc
4,7,9-trioxa-2-aza-8-phosphaundecan-11-aminium, 5-((hexadecyloxy)methyl)-8-hydroxy-n,n,n-trimethyl-3-oxo-, hydroxide, inner salt, 8-oxide, (+-)-
[3-hexadecoxy-2-(methylcarbamoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
FT-0642206
3-(hexadecyloxy)-2-[hydroxy(methylimino)methoxy]propyl 2-(trimethylazaniumyl)ethyl phosphate
DTXSID10911971

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (7.41)	18.7374
1990's	10 (37.04)	18.2507
2000's	13 (48.15)	29.6817
2010's	2 (7.41)	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	27 (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
bisindolylmaleimide i bisindolylmaleimide I: a bis(indolyl)maleimide	2.06	1
chelerythrine chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.	2.06	1	benzophenanthridine alkaloid; organic cation	antibacterial agent; antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
dapi DAPI: RN given refers to parent cpd.	2	1	indoles	fluorochrome
nocodazole [no description available]	2	1	aromatic ketone; benzimidazoles; carbamate ester; thiophenes	antimitotic; antineoplastic agent; microtubule-destabilising agent; tubulin modulator
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	2.06	1	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	2.02	1	mitomycin	alkylating agent; antineoplastic agent
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	2	1	fluorescein isothiocyanate
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.	2.42	2	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
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	2.02	1	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.02	1	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
web 2086 WEB 2086: structure given in first source; PAF antagonist	2.93	4	organonitrogen heterocyclic compound; organosulfur heterocyclic compound
bepafant bepafant: RN given from Toxlit 6/90; PAF antagonist	2.42	2
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	3.62	9	1,2,3-triazole
cv 3988 CV 3988: platelet activating factor antagonist; structure given in first source	1.98	1
cv 6209 CV 6209: platelet activating factor antagonist; structure given in first source	2.01	1
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.	4.48	23	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
bn 50739 BN 50739: platelet activating factor antagonist; structure given in first source	2	1
4-(2-chlorophenyl)-2-(2-(4-isobutylphenyl)ethyl)-6,9-dimethyl-6h-thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepine 4-(2-chlorophenyl)-2-(2-(4-isobutylphenyl)ethyl)-6,9-dimethyl-6H-thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepine: PAF antagonist	2.05	1
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.05	1	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
cariporide cariporide: a selective sodium-hydrogen exchange subtype 1 inhibitor; structure in first source	2.06	1
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	1.99	1
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.	1.99	1	tripeptide
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.02	1	acyl-CoA	acyl donor; coenzyme; effector; fundamental 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.	2.01	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
bn 50730 BN 50730: platelet activating factor antagonist; structure given in first source	2.4	2
modipafant modipafant: structure given in first source ; PAF antagonist	1.99	1
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.01	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	1.97	1	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
barium Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.	2.01	1	alkaline earth metal atom; elemental barium
am-356 methanandamide: structure given in first source; RN given refers to (all-Z)-(+-)-isomer	2.01	1	fatty amide
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	1.99	1	1,2-diacyl-sn-glycero-3-phosphocholine
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.93	4
ginkgolide b [no description available]	2.91	4
cytochalasin d Cytochalasin D: A fungal metabolite that blocks cytoplasmic cleavage by blocking formation of contractile microfilament structures resulting in multinucleated cell formation, reversible inhibition of cell movement, and the induction of cellular extrusion. Additional reported effects include the inhibition of actin polymerization, DNA synthesis, sperm motility, glucose transport, thyroid secretion, and growth hormone release.. cytochalasin D : An organic heterotricyclic compound that is a mycotoxin produced by Helminthosporium and other moulds which is cell permeable and a potent inhibitor of actin polymerisation and DNA synthesis.	2	1

Condition	Relationship Strength	Studies
Metabolic Acidosis [description not available]	2.06	1
Alkalosis A pathological condition that removes acid or adds base to the body fluids.	2.06	1
Acidosis A pathologic condition of acid accumulation or depletion of base in the body. The two main types are RESPIRATORY ACIDOSIS and metabolic acidosis, due to metabolic acid build up.	2.06	1
Carcinoma, Epidermoid [description not available]	2.02	1
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.02	1
Corneal Angiogenesis [description not available]	2.02	1
Corneal Neovascularization New blood vessels originating from the corneal blood vessels and extending from the limbus into the adjacent CORNEAL STROMA. Neovascularization in the superficial and/or deep corneal stroma is a sequel to numerous inflammatory diseases of the ocular anterior segment, such as TRACHOMA, viral interstitial KERATITIS, microbial KERATOCONJUNCTIVITIS, and the immune response elicited by CORNEAL TRANSPLANTATION.	2.02	1
Acquired-Immune Deficiency Syndrome Dementia Complex [description not available]	2.02	1
AIDS Dementia Complex A neurologic condition associated with the ACQUIRED IMMUNODEFICIENCY SYNDROME and characterized by impaired concentration and memory, slowness of hand movements, ATAXIA, incontinence, apathy, and gait difficulties associated with HIV-1 viral infection of the central nervous system. Pathologic examination of the brain reveals white matter rarefaction, perivascular infiltrates of lymphocytes, foamy macrophages, and multinucleated giant cells. (From Adams et al., Principles of Neurology, 6th ed, pp760-1; N Engl J Med, 1995 Apr 6;332(14):934-40)	2.02	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.38	2
Sarcoma, Epithelioid [description not available]	2	1
Cancer of Endometrium [description not available]	2	1
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	2	1
Endometrial Neoplasms Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.	2	1
Di Guglielmo Disease [description not available]	2.01	1
Leucocythaemia [description not available]	2.01	1
Leukemia, Erythroblastic, Acute A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.	2.01	1
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	2.01	1
Arrhythmia [description not available]	2.01	1
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	2.01	1
African Lymphoma [description not available]	1.98	1
Burkitt Lymphoma A form of undifferentiated malignant LYMPHOMA usually found in central Africa, but also reported in other parts of the world. It is commonly manifested as a large osteolytic lesion in the jaw or as an abdominal mass. B-cell antigens are expressed on the immature cells that make up the tumor in virtually all cases of Burkitt lymphoma. The Epstein-Barr virus (HERPESVIRUS 4, HUMAN) has been isolated from Burkitt lymphoma cases in Africa and it is implicated as the causative agent in these cases; however, most non-African cases are EBV-negative.	1.98	1

1-o-hexadecyl-2-n-methylcarbamylphosphatidylcholine

Description

Cross-References

Synonyms (12)

Research

Studies (27)

Market Indicators

Research Demand Index: 11.59

Study Types