Showing metabocard for PC(O-16:0/18:2(9Z,12Z)) (BMDB0011151)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:13:41 UTC
Update Date2020-06-04 20:40:45 UTC
MCDB ID BMDB0011151
Secondary Accession Numbers
  • BMDB11151
Metabolite Identification
Common NamePC(O-16:0/18:2(9Z,12Z))
DescriptionPC(O-16:0/18:2(9Z,12Z)), also known as PC ae C34:2 or PC(O-34:2), belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position. Thus, PC(O-16:0/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(O-16:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(O-16:0/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hexadecyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineChEBI
2-(9Z,12Z-Octadecadienoyl)-1-hexadecyl-sn-glycero-3-phosphocholineHMDB
PC Ae C34:2HMDB
PC(16:0E/18:2(9Z,12Z))HMDB
PC(O-34:2)HMDB
[(2R)-3-Hexadecoxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] 2-trimethylazaniumylethyl phosphateHMDB
Chemical FormulaC42H82NO7P
Average Molecular Weight744.0767
Monoisotopic Molecular Weight743.582890495
IUPAC Name(2-{[(2R)-3-(hexadecyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(hexadecyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry Number88542-95-4
SMILES
CCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C42H82NO7P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-42(44)50-41(40-49-51(45,46)48-38-36-43(3,4)5)39-47-37-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h14,16,20,22,41H,6-13,15,17-19,21,23-40H2,1-5H3/b16-14-,22-20-/t41-/m1/s1
InChI KeyIQACMFWAGALEAQ-WESJWMGVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-alkyl,2-acylglycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-alkyl,2-acylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Glycerol ether
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.86ALOGPS
logP8.66ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity227.55 m³·mol⁻¹ChemAxon
Polarizability92.68 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, Positivesplash10-01q0-9170321300-dbd7856d52c0aa092c202017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-3290111000-2345c437d6514d4c63c62017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-7090022000-2630e93789ae7b7534772017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0090003700-619264aad469d6299fc52017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004u-1091006100-9abf3093eddcb9a13e762017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-4091000000-70d3982de65c2c7f92912017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-23872d2e94db2d9fdf312021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-0060012900-27c3aa121cb366946f752021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4091200000-64e10c7f3565c8d5c6702021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-190e542fe7b67b8c20142021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000000900-190e542fe7b67b8c20142021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0061201900-3adf33f5c1cb71fb83332021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-414ec66860f431bd72762021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-414ec66860f431bd72762021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-1900341600-1c67b05fa14757dd6ff52021-09-24View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.416 +/- 0.002 uM details
Detected and Quantified0.541 +/- 0.004 uM details
Detected and Quantified0.66 +/- 0.01 uM details
Detected and Quantified0.40 +/- 0.01 uM details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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 Compound6443157
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.