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Showing Compound Phosphatidylcholine (FDB019141)

Record Information
Version1.0
Creation date2010-04-08 22:14:10 UTC
Update date2025-11-19 02:17:16 UTC
Primary IDFDB019141
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhosphatidylcholine
DescriptionPC(16:0/18:1(9Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(16:0/18:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
CAS Number6753-55-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-16:0-2-18:1-PhosphatidylcholineChEBI
1-Hexadecanoyl-2-oleoyl-sn-glycero-3-phosphocholineChEBI
1-Palmitoyl-2-oleoyl-GPCChEBI
1-Palmitoyl-2-oleoyl-GPC (16:0/18:1)ChEBI
1-Palmitoyl-2-oleoyl-lecithinChEBI
1-Palmitoyl-2-oleoylphosphatidylcholineChEBI
1-Palmotoyl-2-oleoylglycero-3-phosphocholineChEBI
1-POPCChEBI
16:0-18:1-PCChEBI
GPC(16:0/18:1)ChEBI
GPCho(16:0/18:1)ChEBI
GPCho(16:0/18:1omega9)ChEBI
GPCho(34:1)ChEBI
LecithinChEBI
PalmitoyloleoylphosphatidylcholineChEBI
PC(16:0/18:1)ChEBI
PC(16:0/18:1omega9)ChEBI
PC(34:1)ChEBI
Phosphatidylcholine(16:0/18:1)ChEBI
Phosphatidylcholine(16:0/18:1omega9)ChEBI
Phosphatidylcholine(34:1)ChEBI
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylcholineMeSH
alpha-Phosphatidylcholine-beta-oleoyl-gamma-palmitoylMeSH
1-Palmitoyl-2-oleoyl-phosphatidylcholineMeSH
1-Palmitoyl-2-oleoylphosphatidylcholine, (R)-(Z)-isomerMeSH
POPC LipidMeSH
beta-Oleoyl-gamma-palmitoyl-L-alpha-phosphatidylcholineMeSH
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholineLipid Annotator, MeSH, HMDB
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
PC(16:0/18:1(9Z))Lipid Annotator, ChEBI
1-Palmitoyl-2-oleoyl-3-sn-phosphatidylcholineHMDB
1-Palmitoyl-2-oleoyl-L-alpha-lecithinHMDB
1-Palmitoyl-2-oleoyl-L-alpha-phosphatidylcholineHMDB
1-Palmitoyl-2-oleoyl-L-α-lecithinHMDB
1-Palmitoyl-2-oleoyl-L-α-phosphatidylcholineHMDB
1-Palmitoyl-2-oleoyl-sn-3-phosphocholineHMDB
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphorylcholineHMDB
1-Palmitoyl-2-oleoyl-sn-glycero-phosphatidylcholineHMDB
1-Palmitoyl-2-oleoyl-sn-glycero-phosphocholineHMDB
1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphatidylcholineHMDB
1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholineHMDB
1-Palmitoyl-2-oleoyl-sn-glyceryl-3-phosphorylcholineHMDB
1-Palmitoyl-2-oleoyllecithinHMDB
1-Palmitoyl-2-oleyl-3-sn-phosphatidylcholineHMDB
2-Oleo-1-palmitin phosphate choline esterHMDB
2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholineHMDB
2-Oleoyl-1-palmitoyllecithinHMDB
GPC(16:0/18:1(9Z))HMDB
GPC(16:0/18:1n9)HMDB
GPC(16:0/18:1w9)HMDB
GPC(34:1)HMDB
GPCho(16:0/18:1(9Z))HMDB
GPCho(16:0/18:1n9)HMDB
GPCho(16:0/18:1w9)HMDB
L-1-Palmitoyl-2-oleoylphosphatidylcholineHMDB
L-PalmitoyloleoylphosphatidylcholineHMDB
L-alpha-1-Palmitoyl-2-oleoylphosphatidylcholineHMDB
L-α-1-Palmitoyl-2-oleoylphosphatidylcholineHMDB
PC(16:0/18:1n9)HMDB
PC(16:0/18:1w9)HMDB
POPCHMDB
Phosphatidylcholine(16:0/18:1(9Z))HMDB
Phosphatidylcholine(16:0/18:1n9)HMDB
Phosphatidylcholine(16:0/18:1w9)HMDB
β-Oleoyl-γ-palmitoyl-L-α-phosphatidylcholineHMDB
1,2-Diacyl-sn-glycero-3-phosphocholinebiospider
1,2-Diacylglycero-3-phosphocholinedb_source
3-sn-Phosphatidylcholinebiospider
Choline phosphatidebiospider
Diacyllecithindb_source
Diacylphosphatidylcholinedb_source
E322db_source
Granulestindb_source
Kelecindb_source
Lecitholdb_source
Vitellindb_source
Predicted Properties
PropertyValueSource
Water Solubility2.1e-05 g/LALOGPS
logP5.59ALOGPS
logP8.64ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity226.18 m³·mol⁻¹ChemAxon
Polarizability94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC42H82NO8P
IUPAC name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1
InChI KeyWTJKGGKOPKCXLL-VYOBOKEXSA-N
Isomeric SMILESCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
Average Molecular Weight760.0761
Monoisotopic Molecular Weight759.577805117
Classification
Description Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QqQ 1V, negativesplash10-000t-0090200800-c8db3c4042d858672ebd2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-0006-0020000900-603012fb0ce5ff46f1ea2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 24V, negativesplash10-0udi-0000000190-afc4cd2ac0e64fa396232020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0udl-0000000490-09171592a6955e57e1632020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-0f6x-0000000940-3b9edba3cc0cdfff49452020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0006-0030000910-e80b4b8f6690eea16c9d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-000x-0090000700-527aadfe756a5f2ad9a52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-053r-0090000200-e27632edecd3a83538a42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-053r-0090000000-875a5d38cc2b636df4a12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 72V, negativesplash10-053r-0090000000-6bdad7ea857755dad8df2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 91V, negativesplash10-053r-0090000000-a0160ca0a20b8ca408de2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 109V, negativesplash10-053r-0090000000-d2bc446076d9d86bbadf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 133V, negativesplash10-053r-1090000000-a94d8052959d35d3d25e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 157V, negativesplash10-057i-5190000000-12de950663c450d5ad7f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 194V, negativesplash10-004i-9000000000-906a0ebc0dd0220ac2882020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 53V, negativesplash10-0006-0000000900-0bfd0ce87b7b119d82fb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-0006-0000000900-88f30608c9fd0df934c22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-0006-0000000900-fb159b53855796db7d352020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 34V, negativesplash10-0006-0000000900-084480cec1d6930fa8342020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 41V, negativesplash10-0006-0020000900-103adeac53f8768681222020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 47V, negativesplash10-000x-0090000800-a9198efdf2f4fe5ec5da2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-053r-0090000200-9df170809bae304c6bc12020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-64875131a83d4fda43e62017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000900-dfb450caf9537c97446e2017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fai-1900230300-31ec54e207b217422a2e2017-10-04View Spectrum
NMRNot Available
ChemSpider ID4593686
ChEMBL IDNot Available
KEGG Compound IDC00157
Pubchem Compound ID5497103
Pubchem Substance ID3457
ChEBI ID49183
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0007972
CRC / DFC (Dictionary of Food Compounds) IDLRV43-T:LRV43-T
EAFUS ID2000
Dr. Duke IDLECITHIN|PHOSPHATIDYL-CHOLINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1099111
SuperScent IDNot Available
Wikipedia IDPhosphatidylcholine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-Alzheimeran52217 An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders.DUKE
Anti ataxicAn agent that stimulates movement coordination centers, such as the cerebellum, to treat ataxia, improving balance and motor function, commonly used in managing neurological disorders like multiple sclerosis and spinocerebellar ataxia.DUKE
Anti-cirrhotic52217 An agent that prevents or treats liver cirrhosis, reducing fibrosis and promoting liver health. It inhibits liver scarring, commonly used in managing liver diseases such as hepatitis and fatty liver disease.DUKE
Anti-dementia52217 An agent that slows or prevents cognitive decline, reducing symptoms of dementia. It plays a biological role in neuroprotection, enhancing neuronal function and survival. Therapeutically, it is used to manage Alzheimer's disease, vascular dementia, and other neurodegenerative disorders, improving memory, cognition, and daily functioning.DUKE
Anti dyskineticAn agent that relieves or prevents dyskinesia, improving voluntary movement. It plays a biological role in regulating motor function, and has therapeutic applications in managing Parkinson's disease, Huntington's disease, and other movement disorders, reducing involuntary movements and improving motor control.DUKE
Anti eczemic52217 An agent that reduces inflammation and itching, commonly used to manage eczema symptoms, atopic dermatitis, and other skin allergies, providing relief and preventing flare-ups.DUKE
Anti-lithicAn agent that prevents the formation of calculi (kidney stones) or promotes their dissolution, playing a key role in urology. Its therapeutic applications include managing kidney stone disease, nephrolithiasis, and urinary tract disorders, helping to alleviate pain and prevent complications.DUKE
Anti-manicAn agent that stabilizes mood by controlling symptoms of mania, used to manage bipolar disorder, reducing excessive excitement and impulsivity, and preventing manic episodes.DUKE
Anti-morphinisticAn agent that blocks morphine's activation of the mu opioid receptor, used to treat morphine addiction (morphinism) and manage opioid withdrawal symptoms, reducing dependence and cravings.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti-psoriac52217 An agent that reduces psoriasis symptoms, commonly used in managing plaque psoriasis, scalp psoriasis, and other inflammatory skin conditions, by inhibiting cell growth, reducing inflammation, and modulating the immune system.DUKE
Anti-sclerodermic50177 An agent that prevents or treats scleroderma, a condition characterized by hardened skin and connective tissue. It reduces fibrosis and inflammation, commonly used in managing scleroderma, pulmonary fibrosis, and other fibrotic diseases, improving skin and organ function.DUKE
Anti-seborrheic52217 An agent that reduces seborrheic dermatitis symptoms, commonly used in managing scalp and skin conditions, such as dandruff, itching, and flaking, by inhibiting fungal growth and inflammation.DUKE
Anti-sprueAn antibody associated with celiac sprue, an autoimmune disorder of the small intestine. Its biological role is in immune response, and it has therapeutic applications in diagnosing and monitoring celiac disease, with key medical uses in managing gluten intolerance and intestinal inflammation.DUKE
Anti-Tourette's52217 An agent that reduces tic symptoms, commonly used in managing Tourette's syndrome, with a biological role in regulating neurotransmitter imbalance, and therapeutic applications in reducing involuntary movements and vocalizations, with key medical uses including treatment of tic disorders and associated conditions.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Cholinergic38323 An agent that stimulates the parasympathetic nervous system by mimicking acetylcholine, enhancing muscle contraction, and regulating various bodily functions. Therapeutically, it treats conditions like glaucoma, myasthenia gravis, and Alzheimer's disease, improving muscle tone, cognition, and eye pressure.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
LipotropicA compound that facilitates fat breakdown and metabolism, playing a biological role in lipid utilization. Therapeutically, it's used to enhance weight loss and improve liver function. Key medical applications include treating fatty liver disease, obesity, and hyperlipidemia, making it a valuable agent in managing metabolic disorders.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bland
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).