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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2010-03-18 16:07:54 UTC
Update Date2022-03-07 02:51:30 UTC
HMDB IDHMDB0013455
Secondary Accession Numbers
  • HMDB13455
Metabolite Identification
Common NamePC(O-22:2(13Z,16Z)/22:2(13Z,16Z))
DescriptionPC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 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(O-22:2(13Z,16Z)/22:2(13Z,16Z)), in particular, consists of one chain of Docosadienyl alcohol at the C-1 position and one chain of docosadienoic acid at the C-2 position. The Docosadienyl alcohol moiety is derived from animal fat, while the docosadienoic acid moiety is derived from animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. 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
Data?1582753118
Synonyms
ValueSource
PC(22:2/22:2)Lipid Annotator, HMDB
GPCho(22:2/22:2)Lipid Annotator, HMDB
Phosphatidylcholine(44:4)Lipid Annotator, HMDB
1-Docosadienyl-2-docosadienoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
LecithinLipid Annotator, HMDB
PC(o-22:2(13Z,16Z)/22:2(13Z,16Z))Lipid Annotator
GPCho(44:4)Lipid Annotator, HMDB
PC(44:4)Lipid Annotator, HMDB
1-(13Z,16Z-docosadienyl)-2-(13Z,16Z-docosadienoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
Phosphatidylcholine(22:2/22:2)Lipid Annotator, HMDB
gpcho(22:2n6/22:2n6)HMDB
gpcho(22:2W6/22:2W6)HMDB
PC Ae C44:4HMDB
PC(22:2n6/22:2n6)HMDB
PC(22:2W6/22:2W6)HMDB
PC(O-44:4)HMDB
Phosphatidylcholine(22:2n6/22:2n6)HMDB
Phosphatidylcholine(22:2W6/22:2W6)HMDB
Chemical FormulaC52H98NO7P
Average Molecular Weight880.3108
Monoisotopic Molecular Weight879.708091007
IUPAC Name(2-{[(2R)-3-[(13Z,16Z)-docosa-13,16-dien-1-yloxy]-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(13Z,16Z)-docosa-13,16-dien-1-yloxy]-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C52H98NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h14-17,20-23,51H,6-13,18-19,24-50H2,1-5H3/b16-14-,17-15-,22-20-,23-21-/t51-/m1/s1
InChI KeyGCAMFMBVIXVYSA-VIVKCUGUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-alkyl,2-acylglycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-alkyl,2-acylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Glycerol ether
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.4e-05 g/LALOGPS
logP7.09ALOGPS
logP12.38ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count48ChemAxon
Refractivity275.79 m³·mol⁻¹ChemAxon
Polarizability111.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+314.83130932474
DeepCCS[M-H]-312.94830932474
DeepCCS[M-2H]-346.18630932474
DeepCCS[M+Na]+320.43730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PC(O-22:2(13Z,16Z)/22:2(13Z,16Z))CCCCC\C=C/C\C=C/CCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC5673.5Standard polar33892256
PC(O-22:2(13Z,16Z)/22:2(13Z,16Z))CCCCC\C=C/C\C=C/CCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC5348.6Standard non polar33892256
PC(O-22:2(13Z,16Z)/22:2(13Z,16Z))CCCCC\C=C/C\C=C/CCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC5847.6Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 10V, Positive-QTOFsplash10-0019-9107032230-fd221ac76a433bc194042017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 20V, Positive-QTOFsplash10-0cei-4209021100-31819aa8a85dc752f6fc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 40V, Positive-QTOFsplash10-06s9-7009004210-9128766be59fc0493e6d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 10V, Negative-QTOFsplash10-004r-0007000290-46109b57eace9c21f25f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 20V, Negative-QTOFsplash10-004i-2019200630-6b82709f5d224509f1942017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 40V, Negative-QTOFsplash10-009i-4019200000-69e87fa349b9f78b19ff2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 10V, Negative-QTOFsplash10-004i-0000000090-28c0ee1b28fef89e85882021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 20V, Negative-QTOFsplash10-00or-0004001090-f15ee5c76297b3cfb7452021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 40V, Negative-QTOFsplash10-0079-4009400000-c0a396c92ae9a9408abe2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 10V, Negative-QTOFsplash10-03di-0000000009-f52b9a9681edddda0ddf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 20V, Negative-QTOFsplash10-03di-0000000009-f52b9a9681edddda0ddf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 40V, Negative-QTOFsplash10-0ue0-0007120191-4ce8fbe2ae6ea98b6fb12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 10V, Positive-QTOFsplash10-001i-0000000090-03f6106a76b0f10572b32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 20V, Positive-QTOFsplash10-001i-0000000090-03f6106a76b0f10572b32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(O-22:2(13Z,16Z)/22:2(13Z,16Z)) 40V, Positive-QTOFsplash10-001i-1900061070-e6a838e80bb30c5167772021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.4 (0.33-0.47) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected and Quantified0.39 +/- 0.09 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.46 +/- 0.15 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.25 (0.22-0.3) uMNewborn (0-30 days old)Not Available
Normal
details
FecesDetected and Quantified0.16 +/- 0.1 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.14 +/- 0.08 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.043 +/- 0.004 uMAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified2.13 +/- 0.10 umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.4641 (0.421) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified0.7322 (0.2906) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified0.4(0.1) uMAdult (>18 years old)BothHeart failure with reduced ejection fraction details
BloodDetected and Quantified0.354 +/- 0.114 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.385 +/- 0.110 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
UrineDetected and Quantified2.58 +/- 0.18 umol/mmol creatinineAdolescent (13-18 years old)Both
Obese
details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Obesity
  1. Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
  2. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029455
KNApSAcK IDNot Available
Chemspider ID35032637
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481765
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000865
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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.