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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-12 01:34:25 UTC
Update Date2018-05-20 10:17:38 UTC
HMDB IDHMDB0008283
Secondary Accession Numbers
  • HMDB08283
Metabolite Identification
Common NamePC(20:0/22:1(13Z))
DescriptionPC(20:0/22:1(13Z)) 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(20:0/22:1(13Z)), in particular, consists of one chain of arachidic acid at the C-1 position and one chain of erucic acid at the C-2 position. The arachidic acid moiety is derived from peanut oil, while the erucic acid moiety is derived from seed oils and avocados. 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
Thumb
Synonyms
ValueSource
1-Arachidonyl-2-erucoyl-sn-glycero-3-phosphocholineChEBI
gpcho(20:0/22:1n9)ChEBI
gpcho(20:0/22:1W9)ChEBI
PC(20:0/22:1n9)ChEBI
PC(20:0/22:1W9)ChEBI
Phosphatidylcholine(20:0/22:1n9)ChEBI
Phosphatidylcholine(20:0/22:1W9)ChEBI
Phosphatidylcholine(20:0/22:1)Lipid Annotator
PC(20:0/22:1(13Z))Lipid Annotator
GPCho(42:1)Lipid Annotator
Phosphatidylcholine(42:1)Lipid Annotator
GPCho(20:0/22:1)Lipid Annotator
PC(42:1)Lipid Annotator
LecithinLipid Annotator
1-eicosanoyl-2-(13Z-docosenoyl)-sn-glycero-3-phosphocholineLipid Annotator
PC(20:0/22:1)Lipid Annotator
Chemical FormulaC50H98NO8P
Average Molecular Weight872.2888
Monoisotopic Molecular Weight871.703005629
IUPAC Name(2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-(icosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C50H98NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h20,22,48H,6-19,21,23-47H2,1-5H3/b22-20-/t48-/m1/s1
InChI KeyQXFAPNLFOQKMLO-RURDTVAGSA-N
Chemical Taxonomy
ClassificationNot classified
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 Solubility2.1e-05 g/LALOGPS
logP6.6ALOGPS
logP12.2ChemAxon
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 Count49ChemAxon
Refractivity262.99 m³·mol⁻¹ChemAxon
Polarizability110.93 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-9056041140-8e3e95f550641cc125d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fes-5297021010-6ef510130e6c7e1b708bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fz0-9088002110-add84925e710dba03498View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03kl-0049000040-9e582f0c8a523ee03121View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-0059000100-01bb234aa97021d4ae3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0296-5059100000-e7696b2519a24d3ac804View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.27 (0.22-0.33) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected and Quantified0.32 +/- 0.08 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.28 (0.22-0.34) uMNewborn (0-30 days old)Not Available
Normal
details
FecesDetected and Quantified0.04 +/- 0.03 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.03 +/- 0.01 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.025 +/- 0.009 uMAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.242 +/- 0.097 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.250 +/- 0.084 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.3311 (0.3002) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified0.5457 (0.1542) uMAdult (>18 years old)FemalePregnancy details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.001 +/- 0.002 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood1.000 +/- 0.265 uMAdult (>18 years old)BothNormal (Upper Limit)Calculated using MetaboAnalyst
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. 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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779051
PDB IDNot Available
ChEBI ID86216
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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.