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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-12 01:30:18 UTC
Update Date2018-01-13 00:13:36 UTC
HMDB IDHMDB0008037
Secondary Accession Numbers
  • HMDB08037
Metabolite Identification
Common NamePC(18:0/18:1(11Z))
DescriptionPC(18:0/18:1(11Z)) 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(18:0/18:1(11Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the vaccenic acid moiety is derived from butter fat and animal fat. 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-Stearoyl-2-vaccenoyl-sn-glycero-3-phosphocholineChEBI
gpcho(18:0/18:1)ChEBI
gpcho(18:0/18:1n7)ChEBI
gpcho(18:0/18:1W7)ChEBI
PC(18:0/18:1)ChEBI
PC(18:0/18:1n7)ChEBI
PC(18:0/18:1W7)ChEBI
1-octadecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphocholine; GPCho(18:0/18:1)Lipid Annotator
Phosphatidylcholine(18:0/18:1)Lipid Annotator
GPCho(36:1)Lipid Annotator
PC(36:1)Lipid Annotator
LecithinLipid Annotator
PC(18:0/18:1(11Z))Lipid Annotator
Phosphatidylcholine(36:1)Lipid Annotator
1-octadecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phosphocholineLipid Annotator
Chemical FormulaC44H86NO8P
Average Molecular Weight788.1293
Monoisotopic Molecular Weight787.609105245
IUPAC Nametrimethyl(2-{[(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C44H86NO8P/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/h17,19,42H,6-16,18,20-41H2,1-5H3/b19-17-/t42-/m1/s1
InChI KeyAEAMHDRXCYEOCU-HTDYWKJCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassGlycerophospholipids
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

Industrial application:

  Food and nutrition:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Physiological effect

Organoleptic effect:

  Touch:

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 Solubility1.9e-05 g/LALOGPS
logP5.88ALOGPS
logP9.53ChemAxon
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 Count43ChemAxon
Refractivity235.39 m³·mol⁻¹ChemAxon
Polarizability97.21 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, Positivesplash10-05gi-0000091500-b541b9c1ccc131707404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00m0-0090000400-8ac5a86c021b42ab76c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000100-356447a4f12cdea22c43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-3090100000-612a575f81c6023223d2View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • All Tissues
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified19.8 (16.9-22.8) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected and Quantified40.80 (33.8-47.9) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected and Quantified57.1 +/- 13.5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified60.62(19.39) uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.109 +/- 0.052 uMAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified2.35 +/- 0.13 umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified0.0034 (0.0006-0.025) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified38.8 +/- 13.3 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified47.7 +/- 15.4 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified49.24(14.45) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified34.645 (31.864) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified65.276 (21.905) uMAdult (>18 years old)FemalePregnancy details
UrineDetected and Quantified1.75 +/- 0.10 umol/mmol creatinineAdolescent (13-18 years old)Both
Obese
details
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood5.386642516 +/- 0.591572942 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood66.13333333 +/- 10.43136297 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 Compound24778815
PDB IDNot Available
ChEBI ID86109
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.