Showing metabocard for PC(14:1(9Z)/16:0) (BMDB0007902)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:46:44 UTC
Update Date2020-06-04 19:25:01 UTC
BMDB IDBMDB0007902
Secondary Accession Numbers
  • BMDB07902
Metabolite Identification
Common NamePC(14:1(9Z)/16:0)
DescriptionPC(14:1(9Z)/16:0), also known as gpcho(30:1) or lecithin, 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(14:1(9Z)/16:0) is considered to be a glycerophosphocholine lipid molecule. PC(14:1(9Z)/16:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:1(9Z)/16:0) exists in all eukaryotes, ranging from yeast to humans. PC(14:1(9Z)/16:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:1(9Z)/16:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:1(9Z)/16:0) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:1(9Z)/16:0) can be biosynthesized from CDP-choline and DG(14:1(9Z)/16:0/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:1(9Z)/16:0) and L-serine can be converted into choline and PS(14:1(9Z)/16:0); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(14:1(9Z)/16:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:1(9Z)/16:0) pathway and phosphatidylethanolamine biosynthesis pe(14:1(9Z)/16:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPCho(30:1)HMDB
PC(30:1)HMDB
LecithinHMDB
Phosphatidylcholine(14:1/16:0)HMDB
PC(14:1/16:0)HMDB
Phosphatidylcholine(30:1)HMDB
GPCho(14:1/16:0)HMDB
1-(9Z-Tetradecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphocholineHMDB
1-Myristoleoyl-2-palmitoyl-sn-glycero-3-phosphocholineHMDB
PC(14:1(9Z)/16:0)Lipid Annotator
Chemical FormulaC38H74NO8P
Average Molecular Weight703.9698
Monoisotopic Molecular Weight703.515204861
IUPAC Name(2-{[(2R)-2-(hexadecanoyloxy)-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C38H74NO8P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(41)47-36(35-46-48(42,43)45-33-32-39(3,4)5)34-44-37(40)30-28-26-24-22-20-17-15-13-11-9-7-2/h13,15,36H,6-12,14,16-35H2,1-5H3/b15-13-/t36-/m1/s1
InChI KeyANKCYRKQDLQXGL-MRDDHZETSA-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
logP4.91ALOGPS
logP6.86ChemAxon
logS-7.3ALOGPS
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 Count37ChemAxon
Refractivity207.78 m³·mol⁻¹ChemAxon
Polarizability85.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-484373c40031f84f56b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000900-e86bec38d03a29058b24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1900412100-5259e28a2ec9b26dd27aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-76cb015a5001ccf1d85eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0090042700-6bbbe8f3560bf84f1791View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3294000000-a03ef0bfbd8f621534f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-63c48d3c3566091cd0bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000001900-b22bb941d429955bbe49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-0101791100-33b04cf05db60fba3d1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-2d8ca5019554fe3747deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0030000900-e4f80bd9e3fc3f95b9dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a9i-0090000400-e2909d25bf6adf65ba94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-0c127c4e0d2d526ee55bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000001900-603b5b1686f87c76460eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-0600491100-9f6f8947a96c9c034594View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-7a94d5121f99008ea5f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000900-00d5e9cf26bb924b9286View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1900412100-5ee193d4becfce1ca49cView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.29 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007902
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 Compound52922250
PDB IDNot Available
ChEBI IDNot Available
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(14:1(9Z)/16:0) + L-Serine → Choline + PS(14:1(9Z)/16:0)details