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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-12 01:33:08 UTC
Update Date2020-10-09 21:06:11 UTC
HMDB IDHMDB0008206
Secondary Accession Numbers
  • HMDB08206
Metabolite Identification
Common NamePC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))
DescriptionPC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) 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(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)), in particular, consists of two chains of a-linolenic acid at the C-1 and C-2 positions. The a-linolenic acid moieties are derived from seed oils, especially canola and soybean 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.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?1591649302
Synonyms
ValueSource
GPCho(18:3/18:3)ChEBI
GPCho(18:3n3/18:3n3)ChEBI
GPCho(18:3W3/18:3W3)ChEBI
PC(18:3/18:3)ChEBI
PC(18:3n3/18:3n3)ChEBI
PC(18:3W3/18:3W3)ChEBI
Phosphatidylcholine(18:3/18:3)ChEBI
Phosphatidylcholine(18:3n3/18:3n3)ChEBI
Phosphatidylcholine(18:3W3/18:3W3)ChEBI
Phosphatidylcholine(36:6)HMDB
GPCho(36:6)HMDB
LecithinHMDB
PC(36:6)HMDB
1,2-Di(9Z,12Z,15Z-octadeatrienoyl)-rac-glycero-3-phosphocholineHMDB
1,2-Dia-linolenoyl-rac-glycero-3-phosphocholineHMDB
1,2-Dilinolenoyl-sn-glycero-3-phosphatidylcholineHMDB
1,2-DilinolenoylphosphatidylcholineHMDB
DLPC (Linolenoyl) lipidHMDB
PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))Lipid Annotator, ChEBI
1,2-Dialpha-linolenoyl-GPCHMDB
1,2-Dialpha-linolenoyl-sn-glycero-3-phosphocholineHMDB
1,2-Dialpha-linolenoyl-sn-glycero-phosphatidylcholineHMDB
1,2-Dilinolenoyl-GPCHMDB
1,2-Dilinolenoyl-sn-glycero-3-phosphocholineHMDB
Dilinolenoyl lecithinHMDB
DilinolenoylphosphatidylcholineHMDB
GPC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))HMDB
GPC(18:3/18:3)HMDB
GPC(18:3n3/18:3n3)HMDB
GPC(18:3w3/18:3w3)HMDB
GPC(36:6)HMDB
GPCho(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))HMDB
L-Dilinolenoyl lecithinHMDB
L-alpha-Di(cis,cis,cis-9,12,15-octadecatrienoyl) lecithinHMDB
L-alpha-Dilinolenoyl phosphatidylcholineHMDB
L-α-Di(cis,cis,cis-9,12,15-octadecatrienoyl) lecithinHMDB
L-α-Dilinolenoyl phosphatidylcholineHMDB
Phosphatidylcholine(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))HMDB
Chemical FormulaC44H76NO8P
Average Molecular Weight778.0499
Monoisotopic Molecular Weight777.530854925
IUPAC Name(2-{[(2R)-2,3-bis[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2,3-bis[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number2701-19-1
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C44H76NO8P/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/h8-11,14-17,20-23,42H,6-7,12-13,18-19,24-41H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,23-21-/t42-/m1/s1
InChI KeyXXKFQTJOJZELMD-JICBSJGISA-N
Chemical Taxonomy
Description 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 Descriptors
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 Solubility3.6e-05 g/LALOGPS
logP5.34ALOGPS
logP7.72ChemAxon
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 Count38ChemAxon
Refractivity240.97 m³·mol⁻¹ChemAxon
Polarizability91.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-03di-0030020930-b04a9be78829ff3219a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-003r-0900010500-c970039605c9f604c652Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, positivesplash10-004i-0000000900-f837314e003c3113eb1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 35V, positivesplash10-003r-0900000600-92f5630d60c09ddc321bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, positivesplash10-001i-0900000000-9f98f26880b83576e000Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 59V, positivesplash10-001i-0900000000-4974bb5a3deda8855a56Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 71V, positivesplash10-001i-0900000000-7d7f52656eb8e463d8d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 83V, positivesplash10-001i-1900000000-1b646130ad373ee1f327Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 96V, positivesplash10-001i-3900000000-3b5d29ad855bb63e6937Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 108V, positivesplash10-001i-4900000000-b7301a9f30c5899d2693Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 119V, positivesplash10-001r-6900000000-83408e36a7976e7bf701Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 144V, positivesplash10-003i-9800000000-6ba7dbc7bfc88b830d44Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 180V, positivesplash10-002r-9500000000-cc6f65c360783bb9a2a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 217V, positivesplash10-002s-9300000000-edbc43f25aa0849d3e17Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 265V, positivesplash10-006t-9100000000-35bfcabf3f76210dc62eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 314V, positivesplash10-0002-9000000000-cde5ee66653888ffbd24Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 387V, positivesplash10-0002-9000000000-f8598eeba460ada3ca58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-9051061400-057fe0081044e2f48e7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03yr-6395052200-cdf2814236901dca5853Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-9057043100-252c59a1d38b47e6b1ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000400-09785e8202c3360f75f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0090001000-0668f1ba3bed11b37ad8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4090100000-69fe58cd77008d99959eSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.16 +/- 0.47 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.31 (0.26-0.37) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected and Quantified1.7(0.84) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.4 (0.3-0.54) uMInfant (0-1 year old)Not Available
Normal
details
FecesDetected and Quantified0.03 +/- 0.01 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.17 +/- 0.35 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0037 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0-0.02 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.0 +/- 0.01 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal
    • López Hernández Y...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.574 +/- 0.243 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.725 +/- 0.281 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified1.26(0.59) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified1.1(0.3) uMAdult (>18 years old)BothHeart failure with reduced ejection fraction details
BloodDetected and Quantified1.2059 (1.1361) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified2.1289 (0.9321) uMAdult (>18 years old)FemalePregnancy details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.025 +/- 0.016 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood6.250 +/- 2.407 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
FooDB IDFDB030240
KNApSAcK IDNot Available
Chemspider ID24766868
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24778990
PDB IDNot Available
ChEBI ID86161
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000630
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.