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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-12 01:31:04 UTC
Update Date2018-01-13 00:14:24 UTC
HMDB IDHMDB0008083
Secondary Accession Numbers
  • HMDB08083
Metabolite Identification
Common NamePC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))
DescriptionPC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 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(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of eicosapentaenoic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the eicosapentaenoic acid moiety is derived from fish oils, liver and kidney. 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-Vaccenoyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholineChEBI
gpcho(18:1n7/20:5n3)ChEBI
gpcho(18:1W7/20:5W3)ChEBI
PC(18:1n7/20:5n3)ChEBI
PC(18:1W7/20:5W3)ChEBI
Phosphatidylcholine(18:1n7/20:5n3)ChEBI
Phosphatidylcholine(18:1W7/20:5W3)ChEBI
1-(11Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholine; PC(38:6)Lipid Annotator
GPCho(18:1/20:5)Lipid Annotator
PC(18:1/20:5)Lipid Annotator
GPCho(38:6)Lipid Annotator
Phosphatidylcholine(18:1/20:5)Lipid Annotator
Phosphatidylcholine(38:6)Lipid Annotator
LecithinLipid Annotator
PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))Lipid Annotator
1-(11Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholineLipid Annotator
PC(38:6)Lipid Annotator
Chemical FormulaC46H80NO8P
Average Molecular Weight806.1031
Monoisotopic Molecular Weight805.562155053
IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCC\C=C/CCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C46H80NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h8,10,14,16-17,19-20,22,25,27,31,33,44H,6-7,9,11-13,15,18,21,23-24,26,28-30,32,34-43H2,1-5H3/b10-8-,16-14-,19-17-,22-20-,27-25-,33-31-/t44-/m1/s1
InChI KeyBLXFIBZJVTVAKI-BLPZMAMRSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Disposition

Biological location:

  Cell and elements:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

Source:

  Biological:

Route of exposure:

  Enteral:

Role

Biological role:

Industrial application:

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 Solubility3.1e-05 g/LALOGPS
logP5.75ALOGPS
logP8.61ChemAxon
logS-7.4ALOGPS
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 Count40ChemAxon
Refractivity250.17 m³·mol⁻¹ChemAxon
Polarizability96 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, Positivesplash10-000i-8091041220-67f3a9acaa5dd088dcb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3192011100-72082ee2ab7c6411886cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-8095002100-39f9c7186583f0e391dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w30-0092000030-9ddf1a858783a3803cf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000100-159187ac6aacc532231bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4091000000-5190bdb2750f4981bbcfView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • All Tissues
Pathways
NameSMPDB/PathwhizKEGG
Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))Pw015280Pw015280 greyscalePw015280 simpleNot Available
Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))Pw016120Pw016120 greyscalePw016120 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified60.6 (50.1-72.9 ) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected and Quantified49.1 (37.8-60.8) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected and Quantified88.0 +/- 25.0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified103.41(31.68) uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.030 +/- 0.004 uMAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.13 +/- 0.15 umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified0.001 (0.0005-0.0036) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified51.9 +/- 20.0 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified60.5 +/- 21.7 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified85.74(28.21) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified79.2(25.38) uMAdult (>18 years old)BothHeart failure with reduced ejection fraction details
BloodDetected and Quantified90.567 (84.144) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified178.280 (54.427) uMAdult (>18 years old)FemalePregnancy details
UrineDetected and Quantified0.78 +/- 0.08 umol/mmol creatinineAdolescent (13-18 years old)Both
Obese
details
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0.640885487 +/- 0.179096577 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood61.1 +/- 14.12657071 uMAdult (>18 years old)BothNormal (Upper Limit)Calculated using MetaboAnalyst
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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 Compound24778898
PDB IDNot Available
ChEBI ID86186
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 protein binding
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:
PLD2
Uniprot ID:
O14939
Molecular weight:
104656.485
General function:
Not Available
Specific function:
Not Available
Gene Name:
PLSCR5
Uniprot ID:
A0PG75
Molecular weight:
30026.2
General function:
Involved in calcium ion binding
Specific function:
May play a role in the antiviral response of interferon (IFN) by amplifying and enhancing the IFN response through increased expression of select subset of potent antiviral genes. May contribute to cytokine-regulated cell proliferation and differentiation
Gene Name:
PLSCR1
Uniprot ID:
O15162
Molecular weight:
35048.8
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 ATP binding
Specific function:
May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids in the canicular membrane. May have a role in transport of bile acids into the canaliculus, uptake of bile acids from intestinal contents into intestinal mucosa or both
Gene Name:
ATP8B1
Uniprot ID:
O43520
Molecular weight:
143694.1
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP10A
Uniprot ID:
O60312
Molecular weight:
167686.6
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP8B3
Uniprot ID:
O60423
Molecular weight:
146750.9
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP9A
Uniprot ID:
O75110
Molecular weight:
118581.5
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP10B
Uniprot ID:
O94823
Molecular weight:
165388.9
General function:
Involved in phosphatidylcholine-retinol O-acyltransfera
Specific function:
Transfers the acyl group from the sn-1 position of phosphatidylcholine to all-trans retinol, producing all-trans retinyl esters. Retinyl esters are storage forms of vitamin A. LRAT plays a critical role in vision. It provides the all-trans retinyl ester substrates for the isomerohydrolase which processes the esters into 11-cis-retinol in the retinal pigment epithelium; due to a membrane-associated alcohol dehydrogenase, 11 cis-retinol is oxidized and converted into 11-cis-retinaldehyde which is the chromophore for rhodopsin and the cone photopigments.
Gene Name:
LRAT
Uniprot ID:
O95237
Molecular weight:
25702.635

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.