n-octadecylphosphocholine

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Description

n-octadecylphosphocholine: substrate analog for phospholipase A2 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	125219
CHEMBL ID	198938
SCHEMBL ID	744376
MeSH ID	M0100531

Synonyms (20)

Synonym
ethanaminium,n,n-trimethyl-, inner salt
65956-63-0
nsc-282880
d 19391
octadecylphosphorylcholine
octadecylphosphocholine
nsc282880 ,
NCGC00178095-01
O-0350
n-octadecylphosphocholine
octadecyl 2-(trimethylazaniumyl)ethyl phosphate
d-19391
CHEMBL198938
odpc
ethanaminium, 2-((hydroxy(octadecyloxy)phosphinyl)oxy)-n,n,n-trimethyl-, hydroxide, inner salt
nsc 282880
SCHEMBL744376
o-(octadecylphosphoryl)choline, >=98% (tlc)
choline octadecyl phosphate
DTXSID00984437

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (23)

Assay ID	Title	Year	Journal	Article
AID256233	Hemolytic effect (30 uM) on human erythrocytes upon incubation with lipid for 30 min in pH 7.5	2005	Journal of medicinal chemistry, Oct-06, Volume: 48, Issue:20	Synthesis and biological evaluation of spin-labeled alkylphospholipid analogs.
AID256235	Hemolytic effect (30 uM) on human erythrocytes upon incubation with liposomes for 30 min in pH 7.5; not determined	2005	Journal of medicinal chemistry, Oct-06, Volume: 48, Issue:20	Synthesis and biological evaluation of spin-labeled alkylphospholipid analogs.
AID288963	Toxicity assessed as haemolytic activity against human erythrocytes at 88 uM	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID353105	Activity of human autotaxin in human MBA-MBA-435 cells assessed as effect on enzyme-mediated of FS3 hydrolysis at 0.1 uM	2009	Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9	Autotaxin structure-activity relationships revealed through lysophosphatidylcholine analogs.
AID288958	Inhibition of lipoprotein lipase activity of Cryptococcus neoformans var. grubi H99 secreted PLB1 at 25 uM by radiometric assay method	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID288967	Antibacterial activity against Escherichia coli ATCC 25922 after 24 hrs	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID288962	Toxicity assessed as haemolytic activity against human erythrocytes at 175 uM	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID288955	Antifungal activity against Candida albicans ATCC 10231	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID288966	Toxicity assessed as haemolytic activity against human erythrocytes at 3.5 uM	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID353107	Activity of human autotaxin in human MBA-MBA-435 cells assessed as effect on enzyme-mediated of FS3 hydrolysis at 10 uM	2009	Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9	Autotaxin structure-activity relationships revealed through lysophosphatidylcholine analogs.
AID288965	Toxicity assessed as haemolytic activity against human erythrocytes at 17.5 uM	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID288968	Antibacterial activity against Staphylococcus aureus ATCC 25923 after 24 hrs	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID288954	Antifungal activity against Cryptococcus neoformans ATCC 90112	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID423276	Activity ratio of compound EC50 to miltefosine EC50 for Leishmania donovani MHOM/ET/67/HU3 promastigotes	2007	Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12	Antileishmanial structure-activity relationships of synthetic phospholipids: in vitro and in vivo activities of selected derivatives.
AID288961	Toxicity assessed as haemolytic activity against human erythrocytes at 350 uM	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID423275	Antileishmanial activity against Leishmania donovani MHOM/ET/67/HU3 promastigotes by drug sensitivity assay	2007	Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12	Antileishmanial structure-activity relationships of synthetic phospholipids: in vitro and in vivo activities of selected derivatives.
AID288964	Toxicity assessed as haemolytic activity against human erythrocytes at 44 uM	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID288969	Antibacterial activity against methicillin-resistant Staphylococcus aureus after 24 hrs	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID288970	Antibacterial activity against vancomycin-resistant Enterococcus ATCC 51299 after 24 hrs	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID256232	Hemolytic effect (100 uM) on human erythrocytes; not determined	2005	Journal of medicinal chemistry, Oct-06, Volume: 48, Issue:20	Synthesis and biological evaluation of spin-labeled alkylphospholipid analogs.
AID288957	Inhibition of lipoprotein lipase activity of Cryptococcus neoformans var. grubi H99 secreted PLB1 at 250 uM by radiometric assay method	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID288959	Inhibition of lysophosphatidic acid acyltransferase activity of Cryptococcus neoformans var. grubi H99 secreted PLB1 at 250 uM by radiometric assay method	2007	Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15	Synthesis, antifungal and antimicrobial activity of alkylphospholipids.
AID353106	Activity of human autotaxin in human MBA-MBA-435 cells assessed as effect on enzyme-mediated of FS3 hydrolysis at 1 uM	2009	Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9	Autotaxin structure-activity relationships revealed through lysophosphatidylcholine analogs.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (16.67)	18.7374
1990's	9 (50.00)	18.2507
2000's	5 (27.78)	29.6817
2010's	1 (5.56)	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]

Market Indicators

Research Demand Index: 11.62

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	11.62 (24.57)
Research Supply Index	2.94 (2.92)
Research Growth Index	4.57 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (11.62)

All Compounds (24.57)

Study Types

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	18 (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
choline [no description available]	2.38	2	cholines	allergen; 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.	4	14	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite
edelfosine edelfosine: RN given refers to parent cpd. edelfosine : A racemate comprising equimolar amounts of (R)- and (S)-edelfosine.. 1-octadecyl-2-methylglycero-3-phosphocholine : A glycerophosphocholine that is glycero-3-phosphocholine substituted at positions 1 and 2 by octadecyl and methyl groups respectively.	2.71	3	glycerophosphocholine
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.	3.86	12	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
phenylbutazone Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.	1.99	1	pyrazolidines	antirheumatic drug; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.02	1	xanthene
resazurin resazurin: used as indicator in detection of hyposulfite (sulfoxylate); in food research (reductase test); structure	2.02	1	phenoxazine
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	2.38	2	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
vancomycin Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.	2.03	1	glycopeptide	antibacterial drug; antimicrobial agent; bacterial metabolite
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.	1.98	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
amoxicillin Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.	2.03	1	penicillin allergen; penicillin	antibacterial drug
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).	1.99	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
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.	1.99	1	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
perifosine [no description available]	2.43	2	ammonium betaine; phospholipid	EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor
n-tetradecylphosphorylcholine [no description available]	2.9	4
dodecylphosphocholine dodecylphosphocholine: phospholipase A2 inhibitor; RN refers to chloride. dodecylphosphocholine : A phosphocholine that is the monododecyl ester of phosphocholine	2.41	2	phosphocholines	detergent
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	2.03	1	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial 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.	2.08	1	phosphatidylcholine(1+)
erucylphosphocholine erucylphosphocholine: structure given in first source	2.4	2
chlorhexidine Chlorhexidine: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.. chlorhexidine : A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge.	2.02	1	biguanides; monochlorobenzenes	antibacterial agent; antiinfective agent
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	3.23	6	1,2-diacyl-sn-glycero-3-phosphocholine
arginine Teniposide: A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Teniposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent cells from entering into the mitotic phase of the cell cycle, and lead to cell death. Teniposide acts primarily in the G2 and S phases of the cycle.. teniposide : A furonaphthodioxole that is a synthetic derivative of podophyllotoxin with anti-tumour activity; causes single- and double-stranded breaks in DNA and DNA-protein cross-links and prevents repair by topoisomerase II binding.	1.99	1
glycolipids [no description available]	2.08	1
piperidines Piperidines: A family of hexahydropyridines.	1.99	1

Condition	Relationship Strength	Studies
Extravascular Hemolysis [description not available]	2.69	3
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.69	3
Herpes Simplex Virus Infection [description not available]	1.98	1
Viral Diseases [description not available]	1.98	1
Experimental Mammary Neoplasms [description not available]	2.67	3
Herpes Simplex A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)	1.98	1
Virus Diseases A general term for diseases caused by viruses.	1.98	1
African Sleeping Sickness [description not available]	1.99	1
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	1.99	1
Breast Cancer [description not available]	2.39	2
Leucocythaemia [description not available]	2	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.39	2
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	1
Carcinoma, Anaplastic [description not available]	1.98	1
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	1.98	1
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	1.97	1
B16 Melanoma [description not available]	1.97	1
Experimental Neoplasms [description not available]	2.38	2

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