Showing metabocard for PC(16:1(9Z)/18:0) (BMDB0008003)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:48:48 UTC
Update Date2020-06-04 20:44:21 UTC
BMDB IDBMDB0008003
Secondary Accession Numbers
  • BMDB08003
Metabolite Identification
Common NamePC(16:1(9Z)/18:0)
DescriptionPC(16:1(9Z)/18:0), also known as gpcho(16:1/18:0) or gpcho(34:1), 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(16:1(9Z)/18:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:1(9Z)/18:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:1(9Z)/18:0) exists in all eukaryotes, ranging from yeast to humans. PC(16:1(9Z)/18:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:1(9Z)/18:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/18:0); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:1(9Z)/18:0) can be biosynthesized from CDP-choline and DG(16:1(9Z)/18:0/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:1(9Z)/18:0) and L-serine can be converted into choline and PS(16:1(9Z)/18:0) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(16:1(9Z)/18:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:1(9Z)/18:0) pathway and phosphatidylethanolamine biosynthesis pe(16:1(9Z)/18:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(9Z-Hexadecenoyl)-2-octadecanoyl-sn-glycero-3-phosphocholineChEBI
GPCho(16:1/18:0)ChEBI
GPCho(16:1n7/18:0)ChEBI
GPCho(16:1W7/18:0)ChEBI
PC(16:1/18:0)ChEBI
PC(16:1n7/18:0)ChEBI
PC(16:1W7/18:0)ChEBI
Phosphatidylcholine(16:1/18:0)ChEBI
Phosphatidylcholine(16:1n7/18:0)ChEBI
Phosphatidylcholine(16:1W7/18:0)ChEBI
1-Palmitoleoyl-2-stearoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(34:1)HMDB
LecithinHMDB
PC Aa C34:1HMDB
PC(34:1)HMDB
Phosphatidylcholine(34:1)HMDB
PC(16:1(9Z)/18:0)Lipid Annotator
Chemical FormulaC42H82NO8P
Average Molecular Weight760.0761
Monoisotopic Molecular Weight759.577805117
IUPAC Name(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h17,19,40H,6-16,18,20-39H2,1-5H3/b19-17-/t40-/m1/s1
InChI KeyLJUDFFWSOQEQKW-QCFYSATCSA-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
logP5.59ALOGPS
logP8.64ChemAxon
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 Count41ChemAxon
Refractivity226.18 m³·mol⁻¹ChemAxon
Polarizability93.86 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified26 +/- 1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified16.1 +/- 0.5 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified17.0 +/- 0.2 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified22 +/- 1 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.227 +/- 0.120 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.231 +/- 0.165 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.14 +/- 0.145 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.312 +/- 0.284 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.027 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.03 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.034 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.3 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008003
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025194
KNApSAcK IDNot Available
Chemspider ID24766672
KEGG Compound IDC00157
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922448
PDB IDNot Available
ChEBI ID84570
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(16:1(9Z)/18:0) + L-Serine → Choline + PS(16:1(9Z)/18:0)details