Showing metabocard for PC(18:2(9Z,12Z)/18:2(9Z,12Z)) (BMDB0008138)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
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Record Information
Version1.0
Creation Date2016-10-03 17:14:36 UTC
Update Date2020-06-04 19:46:17 UTC
BMDB IDBMDB0008138
Secondary Accession Numbers
  • BMDB08138
Metabolite Identification
Common NamePC(18:2(9Z,12Z)/18:2(9Z,12Z))
DescriptionPC(18:2(9Z,12Z)/18:2(9Z,12Z)), also known as L-dilinoleoyllecithin or dilinoleoylphosphatidylcholine, 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. Thus, PC(18:2(9Z,12Z)/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:2(9Z,12Z)/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:2(9Z,12Z)/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:2(9Z,12Z)/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:2(9Z,12Z)/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:2(9Z,12Z)/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:2(9Z,12Z)/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(18:2(9Z,12Z)/18:2(9Z,12Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:2(9Z,12Z)/18:2(9Z,12Z)) and L-serine can be converted into choline and PS(18:2(9Z,12Z)/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(18:2(9Z,12Z)/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC44H80NO8P
Average Molecular Weight782.0817
Monoisotopic Molecular Weight781.562155053
IUPAC Name(2-{[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number998-06-1
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C44H80NO8P/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/h14-17,20-23,42H,6-13,18-19,24-41H2,1-5H3/b16-14-,17-15-,22-20-,23-21-/t42-/m1/s1
InChI KeyFVXDQWZBHIXIEJ-LNDKUQBDSA-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
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.68ALOGPS
logP8.44ChemAxon
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
Refractivity238.74 m³·mol⁻¹ChemAxon
Polarizability93.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 21V, positivesplash10-001i-0000000900-bd3ed2ff47d70cb5ac3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-001i-0400000900-d002062176d9e1a58fccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 43V, positivesplash10-001i-0900000100-1d81bafed34be0680f8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, positivesplash10-001i-0900000000-b42fac72a675be84234dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 65V, positivesplash10-001i-0900000000-a1756c5f56f420105ec6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 76V, positivesplash10-001i-0900000000-57ce459f0f2b4ef3b388View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 87V, positivesplash10-001i-1900000000-26d27e14f475fd58e101View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 98V, positivesplash10-001i-2900000000-ee4e32911559ac08e569View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, positivesplash10-001i-3900000000-c96a527426c641063662View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 131V, positivesplash10-003i-7900000000-8fd87469bebc7841cfebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 164V, positivesplash10-002s-9700000000-805c2bda88ecbe768134View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 196V, positivesplash10-002k-9500000000-739389c73c5b7af69f2bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 240V, positivesplash10-0002-9200000000-d6507de242e2b9f69119View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 286V, positivesplash10-0002-9000000000-747c2f7f10ab5dc686cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 351V, positivesplash10-0002-9000000000-e963880e5dd642c7c967View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 54V, positivesplash10-0fe0-0000090600-6c4096785e931bdd859aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 54V, positivesplash10-0006-0000900000-d438f5570e710ae02ee6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 54V, positivesplash10-08fr-0934000000-a2858d3a6aed2e863180View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 54V, positivesplash10-0udi-0300090000-e353c4c82a0a4a7c7e36View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 54V, positivesplash10-000i-9200000000-b6ca8b900ee76df8ea58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-95a10c93ea7d71892a44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-da1f205f6fe8475ad9edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900030300-707d383caeedd787dae6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-2534b1e8e0eb889fbec2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-0080020900-5688f54205e1eea312abView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
  • Placenta
  • Ruminal Fluid
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0008138
DrugBank IDDB04372
Phenol Explorer Compound IDNot Available
FooDB IDFDB030223
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5288075
PDB IDNot Available
ChEBI ID42027
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

Enzyme Details
1. Phosphatidylserine synthase 1
General function:
Not Available
Specific function:
Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:
PTDSS1
Uniprot ID:
Q2KHY9
Molecular weight:
55416.0
Reactions
PC(18:2(9Z,12Z)/18:2(9Z,12Z)) + L-Serine → Choline + PS(18:2(9Z,12Z)/18:2(9Z,12Z))details