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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-04-16 17:00:53 UTC
HMDB IDHMDB0000593
Secondary Accession Numbers
  • HMDB0008104
  • HMDB00593
  • HMDB08104
Metabolite Identification
Common NamePC(18:1(9Z)/18:1(9Z))
DescriptionPC(18:1(9Z)/18:1(9Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(18:1(9Z)/18:1(9Z)), in particular, consists of two chains of oleic acid at the C-1 and C-2 positions. The oleic acid moieties are derived from vegetable oils, especially olive and canola oil. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Dioleoylphosphatidylcholine is found in human platelets and red blood cells, in mitochondria from skeletal muscle, lung, umbilical artery and vein endothelial cells (PMID: 15351277 , 7138900 , 2351875 , 4046747 , 2755318 ).While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.
Structure
Thumb
Synonyms
ValueSource
(Z,Z)-(1)-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxideHMDB
(Z,Z)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxo-9-octadecenyl)oxy]-3,5,9-trioxa-4-phosphaheptacos-18-en-1-aminium 4-oxide hydroxide inner saltHMDB
1,2-Dioleoyl-rac-glycero-3-phosphocholineHMDB
1,2-Dioleoylglycerol-3-phosphorylcholineHMDB
1,2-Dioleoylglyceryl-3-phosphorylcholineHMDB
1,2-DioleoyllecHMDB
DioleoylphosphatidylcholineHMDB
gpcho(18:1/18:1)HMDB
gpcho(18:1n9/18:1n9)HMDB
gpcho(18:1W9/18:1W9)HMDB
gpcho(36:2)HMDB
LecithinHMDB
PC Aa C36:2HMDB
PC(18:1n9/18:1n9)HMDB
PC(18:1W9/18:1W9)HMDB
PC(36:2)HMDB
Phosphatidylcholine(18:1/18:1)HMDB
Phosphatidylcholine(18:1n9/18:1n9)HMDB
Phosphatidylcholine(18:1W9/18:1W9)HMDB
Phosphatidylcholine(36:2)HMDB
1,2-DOCPCMeSH
1,2-Dioleoyl glycerophosphocholineMeSH
1,2-Dioleoyl-sn-glycerol-3-ethylphosphocholineMeSH
1,2-DioleoylglycerophosphocholineMeSH
1,2-Oleoyl-sn-glycero-3-phosphocholineMeSH
1,2-OleoylphosphatidylcholineMeSH
1,2-Oleoylphosphatidylcholine, (e,e)-isomerMeSH
1,2-Oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomerMeSH
1,2-Oleoylphosphatidylcholine, (R-(e,e))-isomerMeSH
1,2-Oleoylphosphatidylcholine, (Z,Z)-(+-)-isomerMeSH
1,2-Oleoylphosphatidylcholine, 14C-labeled, (R-(Z,Z))-isomerMeSH
DOPCMeSH
Dielaidinoyl lecithinMeSH
DielaidoylphosphatidylcholineMeSH
Dioleoyl lecithinMeSH
Dioleoyl phosphatidylcholineMeSH
DioleylphosphatidylcholineMeSH
1,2-di(9Z-octadecenoyl)-rac-glycero-3-phosphocholine; PC(18:1/18:1)Lipid Annotator
PC(18:1(9Z)/18:1(9Z))Lipid Annotator
1,2-di(9Z-octadecenoyl)-rac-glycero-3-phosphocholineLipid Annotator
PC(18:1/18:1)Lipid Annotator
Chemical FormulaC44H84NO8P
Average Molecular Weight786.1134
Monoisotopic Molecular Weight785.593455181
IUPAC Name[2-({2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphonato}oxy)ethyl]trimethylazanium
Traditional Namedioleoylphosphatidylcholine
CAS Registry Number68737-67-7
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-
InChI KeySNKAWJBJQDLSFF-YEUCEMRASA-N
Chemical Taxonomy
DescriptionThis compound 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 DescriptorsNot Available
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.2e-05 g/LALOGPS
logP5.78ALOGPS
logP9.17ChemAxon
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 Count42ChemAxon
Refractivity236.5 m³·mol⁻¹ChemAxon
Polarizability96.78 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0100000900-8d76152294364173953dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-0900000000-db47a3894ce23f083a99View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-0900000000-ac1e031a7d236f329ed9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-36f689a3cf8b031c9ce5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-4df68b8e85813f4b5ad8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900021300-f15a88b3adc3a38193cbView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified44.5 (37.6-53.3) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected and Quantified212 (183-244) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected and Quantified250.7 +/- 47.2 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified267.03(66.1) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified100.0-425.0 uMAdult (>18 years old)BothNormal details
FecesDetected and Quantified0.84 +/- 2 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified1.46 +/- 2.13 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.200 +/- 0.031 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.016 (0.0021-0.045) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0833 +/- 0.2914 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified155.673 (140.706) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified279.018 (74.520) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified192.7 +/- 50.0 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified233.6 +/- 68.4 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified220.75(59.14) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
FecesDetected but not Quantified Newborn (0-30 days old)Not Specified
Premature neonates
details
UrineDetected and Quantified0.0127 +/- 0.0342 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0219 +/- 0.0716 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood242.91 +/- 55.844 uMAdult (>18 years old)BothNormal (Upper Limit)NULL
Blood29.09 +/- 7.79 uMAdult (>18 years old)BothNormal (Most Probable)NULL
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022133
KNApSAcK IDNot Available
Chemspider ID4941669
KEGG Compound IDC00157
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5572
PubChem Compound6437081
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceTokuyama, Satoru; Morisawa, Kazuya; Nakachi, Osamu; Nakano, Yoshiro; Miki, Tomoharu. Preparation of phosphatidylcholines. Jpn. Kokai Tokkyo Koho (1989), 6 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Myher JJ, Kuksis A, Pind S: Molecular species of glycerophospholipids and sphingomyelins of human plasma: comparison to red blood cells. Lipids. 1989 May;24(5):408-18. [PubMed:2755318 ]
  2. Smith RE, Daleke DL: Phosphatidylserine transport in Rhnull erythrocytes. Blood. 1990 Sep 1;76(5):1021-7. [PubMed:2118395 ]
  3. Pigault C, Follenius-Wund A, Schmutz M, Freyssinet JM, Brisson A: Formation of two-dimensional arrays of annexin V on phosphatidylserine-containing liposomes. J Mol Biol. 1994 Feb 11;236(1):199-208. [PubMed:8107105 ]
  4. Knight JD, Miranker AD: Phospholipid catalysis of diabetic amyloid assembly. J Mol Biol. 2004 Aug 27;341(5):1175-87. [PubMed:15321714 ]
  5. Grasso P, Dattatreyamurty B, Reichert LE Jr: Reconstitution of hormone-responsive detergent-solubilized follicle stimulating hormone receptors into liposomes. Mol Endocrinol. 1988 May;2(5):420-30. [PubMed:3138532 ]
  6. Finean JB, Hutchinson AL: X-ray diffraction studies of lipid phase transitions in cholesterol-rich membranes at sub-zero temperatures. Chem Phys Lipids. 1988 Jan;46(1):63-71. [PubMed:3338100 ]
  7. Pinnaduwage P, Huang L: The role of protein-linked oligosaccharide in the bilayer stabilization activity of glycophorin A for dioleoylphosphatidylethanolamine liposomes. Biochim Biophys Acta. 1989 Nov 17;986(1):106-14. [PubMed:2819088 ]
  8. Seppen J, Jansen PL, Oude Elferink RP: Immunoaffinity purification and reconstitution of the human bilirubin/phenol UDP-glucuronosyltransferase family. Protein Expr Purif. 1995 Apr;6(2):149-54. [PubMed:7606162 ]
  9. Larsen CE, Alford DR, Young LJ, McGraw TP, Duzgunes N: Fusion of simian immunodeficiency virus with liposomes and erythrocyte ghost membranes: effects of lipid composition, pH and calcium. J Gen Virol. 1990 Sep;71 ( Pt 9):1947-55. [PubMed:2120385 ]
  10. Anderluh G, Gutierrez-Aguirre I, Rabzelj S, Ceru S, Kopitar-Jerala N, Macek P, Turk V, Zerovnik E: Interaction of human stefin B in the prefibrillar oligomeric form with membranes. Correlation with cellular toxicity. FEBS J. 2005 Jun;272(12):3042-51. [PubMed:15955063 ]
  11. Billy D, Speijer H, Lindhout T, Hemker HC, Willems GM: Inhibition of prothrombinase at macroscopic lipid membranes: competition between antithrombin and prothrombin. Biochemistry. 1995 Oct 17;34(41):13699-704. [PubMed:7577961 ]
  12. Versluis AJ, Rensen PC, Kuipers ME, Love WG, Taylor PW: Interaction between zinc(II)-phthalocyanine-containing liposomes and human low density lipoprotein. J Photochem Photobiol B. 1994 May;23(2-3):141-8. [PubMed:8040754 ]
  13. Mahadevappa VG, Holub BJ: The molecular species composition of individual diacyl phospholipids in human platelets. Biochim Biophys Acta. 1982 Oct 14;713(1):73-9. [PubMed:7138900 ]
  14. Ritov VB, Menshikova EV, Kelley DE: High-performance liquid chromatography-based methods of enzymatic analysis: electron transport chain activity in mitochondria from human skeletal muscle. Anal Biochem. 2004 Oct 1;333(1):27-38. [PubMed:15351277 ]
  15. Takamura H, Kasai H, Arita H, Kito M: Phospholipid molecular species in human umbilical artery and vein endothelial cells. J Lipid Res. 1990 Apr;31(4):709-17. [PubMed:2351875 ]
  16. Itoh K, Suzuki A, Kuroki Y, Akino T: High performance liquid chromatographic separation of diacylglycerol acetates to quantitate disaturated species of lung phosphatidylcholine. Lipids. 1985 Sep;20(9):611-6. [PubMed:4046747 ]

Only showing the first 10 proteins. There are 78 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:
LYPLA1
Uniprot ID:
O75608
Molecular weight:
24669.355
General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:
PLA2G15
Uniprot ID:
Q8NCC3
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in hydrolase activity
Specific function:
May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:
LYPLA2
Uniprot ID:
O95372
Molecular weight:
24736.71

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates ATP-dependent export of organic anions and drugs from the cytoplasm. Hydrolyzes ATP with low efficiency. Human MDR3 is not capable of conferring drug resistance. Mediates the translocation of phosphatidylcholine across the canalicular membrane of the hepatocyte
Gene Name:
ABCB4
Uniprot ID:
P21439
Molecular weight:
141521.8

Only showing the first 10 proteins. There are 78 proteins in total.