Compounds > 1,2-didecanoylphosphatidylcholine
Page last updated: 2024-12-08

1,2-didecanoylphosphatidylcholine

Description

## 1,2-Didecanoylphosphatidylcholine (DDPC): A Model Phospholipid

1,2-Didecanoylphosphatidylcholine (DDPC) is a **synthetic phospholipid** that is commonly used in research. It is a **model lipid** that mimics the structure and properties of natural phospholipids found in cell membranes.

Here's a breakdown of why it's important in research:

**Structure and Properties:**

* **Structure:** DDPC has a similar head group and two acyl chains as natural phospholipids. Its head group is a **choline** molecule, and the two acyl chains are **decanoic acid**, which is a saturated fatty acid with 10 carbon atoms.
* **Properties:** DDPC is a **highly water-soluble** lipid due to its polar choline head group. It forms **stable bilayers** in aqueous solutions, mimicking the structure of cell membranes. Its **saturated acyl chains** give it a high melting point and make it more rigid than unsaturated phospholipids.

**Applications in Research:**

DDPC is a valuable tool for research in a wide range of fields, including:

* **Membrane Biology:**
* DDPC is used to study the **structure and function of cell membranes** in model systems.
* It helps researchers understand how lipids interact with proteins and other membrane components.
* Researchers use it to study the effects of drugs and toxins on membrane properties.
* **Biophysics:**
* DDPC is used to investigate the **physical properties of lipid bilayers**, including their fluidity, permeability, and elasticity.
* It is used to study how lipid bilayers respond to environmental changes like temperature and pH.
* **Drug Delivery:**
* DDPC is used to develop **novel drug delivery systems**, taking advantage of its ability to form liposomes, which are vesicles made of lipid bilayers.
* **Biomaterials:**
* DDPC is used as a component of biomaterials, including **artificial membranes and cell culture substrates**.

**Advantages of using DDPC:**

* **Simplicity:** DDPC is a simple, well-defined molecule, making it easier to study its properties and interactions.
* **Stability:** It is relatively stable in aqueous solutions and can be stored for extended periods.
* **Versatility:** DDPC can be used in various experimental techniques, including microscopy, spectroscopy, and chromatography.

**Limitations of using DDPC:**

* **Lack of biological complexity:** DDPC is a simplified model of natural phospholipids and doesn't capture the full complexity of cell membranes.
* **Saturated acyl chains:** DDPC's saturated acyl chains make it more rigid than natural phospholipids, which often have unsaturated acyl chains.

**Overall, DDPC is a powerful tool for researchers studying the fundamental properties of cell membranes and developing new applications in medicine and biotechnology.**

1,2-didecanoylphosphatidylcholine: RN given refers to parent compound [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID166886
CHEMBL ID114624
CHEBI ID182631
SCHEMBL ID235645
MeSH IDM0064184

Synonyms (23)

Synonym
2,3-di(decanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
CHEBI:182631
13699-47-3
1,2-didecanoylphosphatidylcholine
CHEMBL114624
3,5,9-trioxa-4-phosphanonadecan-1-aminium, 4-hydroxy-n,n,n-trimethyl-10-oxo-7-((1-oxodecyl)oxy)-, inner salt, 4-oxide
dicaprylphosphatidylcholine
6ilb57epfe ,
unii-6ilb57epfe
FT-0627671
SCHEMBL235645
10:0 pc
didecanoylphosphatidylcholine, dl-
didecanoylglycerophosphocholine, dl-
1,2-didecanoyl pc
J-019569
DTXSID70929618
2,3-bis(decanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
1,2-didecanoyl phosphatidylcholine
Q27264968
dl-didecanoylphosphatidylcholine
didecanoyl lecithin
PD049033

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Plasma concentrations of the hormone were determined until 240 min post administration by ELISA, and the absolute bioavailability was estimated to be in the vicinity of 20%."( Epithelial transport and bioavailability of intranasally administered human growth hormone formulated with the absorption enhancers didecanoyl-L-alpha-phosphatidylcholine and alpha-cyclodextrin in rabbits.
Agerholm, C; Bastholm, L; Elling, F; Johansen, PB; Nielsen, MH, 1994)		0.29
[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]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID18294Michaelis -Menten constant against phospholipase A2 was determined1999Bioorganic & medicinal chemistry letters, Feb-08, Volume: 9, Issue:3
Quantitative analysis of the kinetics of phospholipase A2 using fast atom bombardment mass spectrometry.
AID17471Catalytic rate constant against phospholipase A2 was determined1999Bioorganic & medicinal chemistry letters, Feb-08, Volume: 9, Issue:3
Quantitative analysis of the kinetics of phospholipase A2 using fast atom bombardment mass spectrometry.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (7.14)18.7374
1990's9 (64.29)18.2507
2000's4 (28.57)29.6817
2010's0 (0.00)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 (%)
Trials1 (6.25%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
bromide
Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)		2.0310halide anion;
monoatomic bromine
chlorine
chloride : A halide anion formed when chlorine picks up an electron to form an an anion.		2.4120halide anion;
monoatomic chlorine		cofactor;
Escherichia coli metabolite;
human metabolite
urea
pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.		2.0310isourea;
monocarboxylic acid amide;
one-carbon compound		Daphnia magna metabolite;
Escherichia coli metabolite;
fertilizer;
flour treatment agent;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
haloperidol
Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.		1.9810aromatic ketone;
hydroxypiperidine;
monochlorobenzenes;
organofluorine compound;
tertiary alcohol		antidyskinesia agent;
antiemetic;
dopaminergic antagonist;
first generation antipsychotic;
serotonergic antagonist
potassium chloride
Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.		2.0310inorganic chloride;
inorganic potassium salt;
potassium salt		fertilizer
sucrose
Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.		2.3920glycosyl glycosidealgal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
sweetening agent
amiloride
Amiloride: A pyrazine compound inhibiting SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with DIURETICS to spare POTASSIUM loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705). amiloride : A member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid.		1.9810aromatic amine;
guanidines;
organochlorine compound;
pyrazines		diuretic;
sodium channel blocker
deoxycholic acid
Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.		1.9910bile acid;
C24-steroid;
dihydroxy-5beta-cholanic acid		human blood serum metabolite
betadex
beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.		1.9910cyclodextrin
alpha-cyclodextrin
alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.		1.9810cyclodextrin
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.		2.03101,2-diacyl-sn-glycero-3-phosphocholine(1+)
fusidic acid
Fusidic Acid: An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed). It acts by inhibiting translocation during protein synthesis.. fusidic acid : A steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum.		1.991011alpha-hydroxy steroid;
3alpha-hydroxy steroid;
alpha,beta-unsaturated monocarboxylic acid;
steroid acid;
steroid antibiotic;
sterol ester		EC 2.7.1.33 (pantothenate kinase) inhibitor;
Escherichia coli metabolite;
protein synthesis inhibitor
tauro-24,25-dihydrofusidate
tauro-24,25-dihydrofusidate: affects nasal absorption of insulin in sheep		1.9910
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.		1.9910prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic
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.		2.4320phosphatidylcholine(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).		2.43201,2-diacyl-sn-glycero-3-phosphocholine;
phosphatidylcholine 28:0;
tetradecanoate ester		antigen;
mouse metabolite
1,2-dielaidoylphosphatidylethanolamine
1,2-dielaidoylphosphatidylethanolamine: RN given refers to (E,E)-isomer; member of a class of cationic lipid formulations called cytofectins		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.		1.9810
glucagon
Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.		1.9610peptide hormone
phosphatidylcholines
Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.		3.941301,2-diacyl-sn-glycero-3-phosphocholine
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		0210
Autosomal Hemophilia A
[description not available]		02.0310
Hemophilia A
The classic hemophilia resulting from a deficiency of factor VIII. It is an inherited disorder of blood coagulation characterized by a permanent tendency to hemorrhage.		02.0310
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