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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-12-10 02:07:41 UTC
Update Date2022-03-07 02:51:07 UTC
HMDB IDHMDB0011331
Secondary Accession Numbers
  • HMDB11331
Metabolite Identification
Common NamePC(P-18:1(9Z)/P-16:0)
DescriptionPC(P-18:1(9Z)/P-16:0) 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(P-18:1(9Z)/P-16:0), in particular, consists of one chain of plasmalogen 18:1n9 at the C-1 position and one chain of plasmalogen 16:0 at the C-2 position. The plasmalogen 18:1n9 moiety is derived from animal fats, liver and kidney, while the plasmalogen 16:0 moiety is derived from animal fats, 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.
Structure
Data?1582752895
Synonyms
ValueSource
(2R)-2-[(1Z)-Hexadec-1-en-1-yloxy]-3-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]propyl 2-(trimethylazaniumyl)ethyl phosphoric acidGenerator
Chemical FormulaC42H82NO6P
Average Molecular Weight728.093
Monoisotopic Molecular Weight727.587976362
IUPAC Name(2R)-2-[(1Z)-hexadec-1-en-1-yloxy]-3-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]propyl 2-(trimethylazaniumyl)ethyl phosphate
Traditional Name(2R)-2-[(1Z)-hexadec-1-en-1-yloxy]-3-[(1Z,9Z)-octadeca-1,9-dien-1-yloxy]propyl 2-(trimethylammonio)ethyl phosphate
CAS Registry NumberNot Available
SMILES
[H][C@@](CO\C=C/CCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)O\C=C/CCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C42H82NO6P/c1-6-8-10-12-14-16-18-20-22-23-24-26-28-30-32-34-37-46-40-42(41-49-50(44,45)48-39-36-43(3,4)5)47-38-35-33-31-29-27-25-21-19-17-15-13-11-9-7-2/h20,22,34-35,37-38,42H,6-19,21,23-33,36,39-41H2,1-5H3/b22-20-,37-34-,38-35-/t42-/m1/s1
InChI KeyDKCXAWVKSPBFRB-BCZCSWKFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentGlycerophosphocholines
Alternative Parents
Substituents
  • Glycero-3-phosphocholine
  • Phosphocholine
  • Glycerol vinyl ether
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP6.34ALOGPS
logP9.43ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area77.05 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity226.86 m³·mol⁻¹ChemAxon
Polarizability90.88 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+289.92130932474
DeepCCS[M-H]-286.62330932474
DeepCCS[M-2H]-320.95930932474
DeepCCS[M+Na]+297.23830932474
AllCCS[M+H]+287.032859911
AllCCS[M+H-H2O]+286.832859911
AllCCS[M+NH4]+287.232859911
AllCCS[M+Na]+287.232859911
AllCCS[M-H]-277.532859911
AllCCS[M+Na-2H]-281.932859911
AllCCS[M+HCOO]-286.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PC(P-18:1(9Z)/P-16:0)[H][C@@](CO\C=C/CCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)O\C=C/CCCCCCCCCCCCCC5079.7Standard polar33892256
PC(P-18:1(9Z)/P-16:0)[H][C@@](CO\C=C/CCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)O\C=C/CCCCCCCCCCCCCC4153.9Standard non polar33892256
PC(P-18:1(9Z)/P-16:0)[H][C@@](CO\C=C/CCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)O\C=C/CCCCCCCCCCCCCC4885.5Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 10V, Negative-QTOFsplash10-004i-0090002800-a078e99750559522b0692019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 20V, Negative-QTOFsplash10-016r-1090104100-1298834d33327561bb2c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 40V, Negative-QTOFsplash10-0170-3090200000-fb5c5d7f8578613ec3d52019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 10V, Negative-QTOFsplash10-004i-0000000900-108cb09bf84194a629e82021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 20V, Negative-QTOFsplash10-004i-0010013900-6ea37a0d6063902d03522021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 40V, Negative-QTOFsplash10-004i-9142010000-f0e9e99a7979a71c373c2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 10V, Positive-QTOFsplash10-000i-9120131300-a4788e57f1ebd469ceaf2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 20V, Positive-QTOFsplash10-000b-7391134000-d4a32660de41ee4ccdbb2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 40V, Positive-QTOFsplash10-0081-9081053000-739c8cf820e22798e59a2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 10V, Positive-QTOFsplash10-004i-3200011900-7b995ad79541fc641ef62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 20V, Positive-QTOFsplash10-053r-9600025100-3dcacd4f2e8e9d3d81522021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PC(P-18:1(9Z)/P-16:0) 40V, Positive-QTOFsplash10-001i-2900000000-6ca085773872c51e5f9d2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified242.2 +/- 51.3 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified105 (91.8-119) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected and Quantified173 (145-199) uMInfant (0-1 year old)Not Available
Normal
details
FecesDetected and Quantified2.21 +/- 1.94 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.65 +/- 0.67 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.214 +/- 0.082 uMAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified4.00 +/- 0.35 umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified0.0077 (0.0023-0.05) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified170.6 +/- 49.9 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified208.6 +/- 57.9 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified168.65 (151.577) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified316.441 (96.259) uMAdult (>18 years old)FemalePregnancy details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
UrineDetected and Quantified2.86 +/- 0.18 umol/mmol creatinineAdolescent (13-18 years old)Both
Obese
details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.010 +/- 0.009 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood2.033 +/- 1.762 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. Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
  2. 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 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 Compound131801677
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029960
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 72 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 metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635
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

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 72 proteins in total.