Showing metabocard for PC(16:1(9Z)/P-18:1(11Z)) (BMDB0008029)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:49:19 UTC
Update Date2020-06-04 20:00:33 UTC
BMDB IDBMDB0008029
Secondary Accession Numbers
  • BMDB08029
Metabolite Identification
Common NamePC(16:1(9Z)/P-18:1(11Z))
DescriptionPC(16:1(9Z)/P-18:1(11Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(16:1(9Z)/P-18:1(11Z)), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one 1Z,11Z-octadecadienyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Palmitoleoyl-2-(1-enyl-vaccenoyl)-sn-glycero-3-phosphocholineHMDB
Gpcho(16:1/18:1)HMDB
Gpcho(16:1n7/18:1n7)HMDB
Gpcho(16:1W7/18:1W7)HMDB
Gpcho(34:2)HMDB
LecithinHMDB
PC Aa C34:2HMDB
PC(16:1/18:1)HMDB
PC(16:1n7/18:1n7)HMDB
PC(16:1W7/18:1W7)HMDB
PC(34:2)HMDB
Phosphatidylcholine(16:1/18:1)HMDB
Phosphatidylcholine(16:1n7/18:1n7)HMDB
Phosphatidylcholine(16:1W7/18:1W7)HMDB
Phosphatidylcholine(34:2)HMDB
Chemical FormulaC42H80NO7P
Average Molecular Weight742.0609
Monoisotopic Molecular Weight741.567240431
IUPAC Name[2-({3-[(9Z)-hexadec-9-enoyloxy]-2-[(1Z,11Z)-octadeca-1,11-dien-1-yloxy]propyl phosphonato}oxy)ethyl]trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCC\C=C/CCCCCCCC\C=C/OC(COC(=O)CCCCCCC\C=C/CCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C42H80NO7P/c1-6-8-10-12-14-16-18-20-21-22-24-26-28-30-32-34-37-47-41(40-50-51(45,46)49-38-36-43(3,4)5)39-48-42(44)35-33-31-29-27-25-23-19-17-15-13-11-9-7-2/h16-19,34,37,41H,6-15,20-33,35-36,38-40H2,1-5H3/b18-16-,19-17-,37-34-
InChI KeyZFACUKICYTXONE-IWDZABBFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl,2-(1z-alkenyl)-glycerophosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O1-position, and one 1Z-alkenyl chain attached through an ether linkage at the O2-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl,2-(1Z-alkenyl)-glycerophosphocholines
Alternative Parents
Substituents
  • 1-acyl,2-(1z-alkenyl)-glycerophosphocholine
  • Phosphocholine
  • Glycerol vinyl ether
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not 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
logP5.85ALOGPS
logP8.67ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity227.64 m³·mol⁻¹ChemAxon
Polarizability91.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9050321300-98a37ca451116d7940edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5292121000-ebb09ca3445f18a51770View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-8092033000-3b999ebacd18124e7200View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f7c-0090000300-d1ca2bf0ebeb8134fd03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0090001000-873e58e1eafa26c7bb8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kbr-3090000000-b120615ce0ca70487ac9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-eda6b98afc513e9474e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0060003900-790f136240e2577c8e23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-7292100000-141bf839e3f4929e752fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2200001900-6b095b0f3e4eb96983a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-4900001100-f82334e79ffa6355b009View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2900000000-6053a195be10dd67af33View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008029
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025220
KNApSAcK IDNot Available
Chemspider ID24766698
KEGG Compound IDC00157
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478697
PDB IDNot Available
ChEBI ID89648
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available