Showing metabocard for PC(24:0/22:2(6Z,13Z)) (BMDB0063630)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-11-07 18:04:53 UTC
Update Date2020-06-04 19:50:39 UTC
MCDB ID BMDB0063630
Secondary Accession Numbers
  • BMDB63630
Metabolite Identification
Common NamePC(24:0/22:2(6Z,13Z))
DescriptionPC(24:0/22:2(6Z,13Z)) is a phosphatidylchloline (PC or GPCho). 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. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(24:0/22:2(6Z,13Z)), in particular, consists of one tetracosanoyl chain to the C-1 atom, and one 6Z,13Z-docosadienoyl 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. PCs can also be synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC54H104NO8P
Average Molecular Weight926.399
Monoisotopic Molecular Weight925.749956311
IUPAC Name(2-{[(2R)-2-[(6Z,13Z)-docosa-6,13-dienoyloxy]-3-(tetracosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-[(6Z,13Z)-docosa-6,13-dienoyloxy]-3-(tetracosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/CCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C54H104NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-27-29-30-32-34-36-38-40-42-44-46-53(56)60-50-52(51-62-64(58,59)61-49-48-55(3,4)5)63-54(57)47-45-43-41-39-37-35-33-31-28-25-23-21-19-17-15-13-11-9-7-2/h21,23,37,39,52H,6-20,22,24-36,38,40-51H2,1-5H3/b23-21-,39-37-/t52-/m1/s1
InChI KeyQYVKBNMHUYGIRK-IHXGGWPCSA-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
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.08ALOGPS
logP13.61ChemAxon
logS-7.7ALOGPS
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 Count52ChemAxon
Refractivity282.51 m³·mol⁻¹ChemAxon
Polarizability116.84 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-8009030113-619ef7ba0581463caa392019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-1013-4219110101-1ea0193396fd10e2620f2019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-055r-9028400230-c792cf200c6b481e35b62019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ba-0009000002-871f9e8248d19ba438ec2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000010-ddc6f7f52df17947927f2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-4019000000-8c8c169fadd5f996ca262019-02-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified1.7 +/- 0.1 uM details
Detected and Quantified2.5 +/- 0.4 uM details
Detected and Quantified5.0 +/- 0.1 uM details
Detected and Quantified0.9 +/- 0.1 uM details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID75320560
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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.