You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2010-03-18 16:07:57 UTC
Update Date2018-01-13 00:23:29 UTC
HMDB IDHMDB0013458
Secondary Accession Numbers
  • HMDB13458
Metabolite Identification
Common NamePC(o-24:0/18:3(6Z,9Z,12Z))
DescriptionPC(o-24:0/18:3(6Z,9Z,12Z)) 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-24:0/18:3(6Z,9Z,12Z)), in particular, consists of one chain of Lignoceryl alcohol at the C-1 position and one chain of g-linolenic acid at the C-2 position. The Lignoceryl alcohol moiety is derived from plant waxes and beeswax, while the g-linolenic 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
Thumb
Synonyms
ValueSource
1-Lignoceryl-2-g-linolenoyl-sn-glycero-3-phosphocholineHMDB
1-Lignoceryl-2-gamma-linolenoyl-sn-glycero-3-phosphocholineHMDB
gpcho(24:0/18:3)HMDB
gpcho(24:0/18:3n6)HMDB
gpcho(24:0/18:3W6)HMDB
gpcho(42:3)HMDB
LecithinHMDB
PC Ae C42:3HMDB
PC(24:0/18:3)HMDB
PC(24:0/18:3n6)HMDB
PC(24:0/18:3W6)HMDB
PC(42:3)HMDB
PC(O-42:3)HMDB
Phosphatidylcholine(24:0/18:3)HMDB
Phosphatidylcholine(24:0/18:3n6)HMDB
Phosphatidylcholine(24:0/18:3W6)HMDB
Phosphatidylcholine(42:3)HMDB
1-Tetracosanyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholine; Phosphatidylcholine(24:0/18:3)Lipid Annotator
PC(o-24:0/18:3(6Z,9Z,12Z))Lipid Annotator
1-Tetracosanyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholineLipid Annotator
Chemical FormulaC50H96NO7P
Average Molecular Weight854.2735
Monoisotopic Molecular Weight853.692440943
IUPAC Nametrimethyl(2-{[(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(tetracosyloxy)propyl phosphonato]oxy}ethyl)azanium
Traditional Nametrimethyl(2-{[(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(tetracosyloxy)propyl phosphonato]oxy}ethyl)azanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C50H96NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-27-28-30-32-34-36-38-40-42-45-55-47-49(48-57-59(53,54)56-46-44-51(3,4)5)58-50(52)43-41-39-37-35-33-31-29-21-19-17-15-13-11-9-7-2/h15,17,21,29,33,35,49H,6-14,16,18-20,22-28,30-32,34,36-48H2,1-5H3/b17-15-,29-21-,35-33-/t49-/m1/s1
InChI KeyLDFITNYTODJQBW-AQBSXLNYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Biological location:

  Cell and elements:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

Source:

  Biological:

Route of exposure:

  Enteral:

Role

Biological role:

Industrial application:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

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 Solubility2.3e-05 g/LALOGPS
logP6.97ALOGPS
logP11.85ChemAxon
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 Count47ChemAxon
Refractivity265.47 m³·mol⁻¹ChemAxon
Polarizability108.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • All Tissues
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.6 (0.50-0.72) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected and Quantified0.40-2.20 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.84 +/- 0.18 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.92(0.27) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.47 (0.37-0.63) uMNewborn (0-30 days old)Not Available
Normal
details
SalivaDetected and Quantified0.013 +/- 0.003 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.0011 +/- 0.0014 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0007 (0.0001-0.002) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.8538 (0.817) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified1.3914 (0.4665) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified0.79(0.2) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified0.79(0.16) uMAdult (>18 years old)BothHeart failure with reduced ejection fraction details
BloodDetected and Quantified0.579 +/- 0.170 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.630 +/- 0.185 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
UrineDetected and Quantified0.0009 +/- 0.0008 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0011 +/- 0.0012 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029458
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481771
PDB IDNot Available
ChEBI ID86451
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 44 proteins in total.

Enzymes

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:
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 phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Molecular weight:
21066.99
General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Central enzyme in the extracellular metabolism of plasma lipoproteins. Synthesized mainly in the liver and secreted into plasma where it converts cholesterol and phosphatidylcholines (lecithins) to cholesteryl esters and lysophosphatidylcholines on the surface of high and low density lipoproteins (HDLs and LDLs). The cholesterol ester is then transported back to the liver. Has a preference for plasma 16:0-18:2 or 18:O-18:2 phosphatidylcholines. Also produced in the brain by primary astrocytes, and esterifies free cholesterol on nascent APOE-containing lipoproteins secreted from glia and influences cerebral spinal fluid (CSF) APOE- and APOA1 levels. Together with APOE and the cholesterol transporter ABCA1, plays a key role in the maturation of glial-derived, nascent lipoproteins. Required for remodeling high-density lipoprotein particles into their spherical forms.
Gene Name:
LCAT
Uniprot ID:
P04180
Molecular weight:
49577.545
General function:
Involved in phospholipase A2 activity
Specific function:
Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G2A
Uniprot ID:
P14555
Molecular weight:
16082.525
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other phospholipids examined.
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Molecular weight:
16546.1

Only showing the first 10 proteins. There are 44 proteins in total.