Showing metabocard for PC(o-14:0/16:0) (LMDB00585)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:53:07 UTC
Update Date2016-07-20 20:45:53 UTC
LmdbLMDB00585
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(o-14:0/16:0)
DescriptionPC(o-14:0/16:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(o-14:0/16:0), in particular, consists of one chain of Myristyl alcohol at the C-1 position and one chain of palmitic acid at the C-2 position. The Myristyl alcohol moiety is derived from butter oil, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also 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
Synonyms
ValueSource
1-Myristyl-2-palmitoyl-sn-glycero-3-phosphocholineChEBI
Gpcho(14:0/16:0)HMDB
Gpcho(30:0)HMDB
LecithinHMDB
PC Ae C30:0HMDB
PC(14:0/16:0)HMDB
PC(30:0)HMDB
PC(O-30:0)HMDB
Phosphatidylcholine(14:0/16:0)HMDB
Phosphatidylcholine(30:0)HMDB
1-Tetradecanyl-2-hexadecanoyl-sn-glycero-3-phosphocholineHMDB
PC(o-14:0/16:0)Lipid Annotator
Chemical FormulaC38H78NO7P
Average Molecular Weight692.0022
Monoisotopic Molecular Weight691.551590367
IUPAC Name(2-{[(2R)-2-(hexadecanoyloxy)-3-(tetradecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-(hexadecanoyloxy)-3-(tetradecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C38H78NO7P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-38(40)46-37(36-45-47(41,42)44-34-32-39(3,4)5)35-43-33-30-28-26-24-22-19-17-15-13-11-9-7-2/h37H,6-36H2,1-5H3/t37-/m1/s1
InChI KeyBYMZZQJJOHDZOU-DIPNUNPCSA-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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot 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
logP5.29ALOGPS
logP7.61ChemAxon
logS-7.4ALOGPS
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 Count38ChemAxon
Refractivity206.91 m³·mol⁻¹ChemAxon
Polarizability87.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08mj-9740556000-3e9e7266e142695dcf02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9260314000-1375fa09f32711c370c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-6690221000-f6795c8ca1591f425f84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-9360021000-df3b35b7dc7ea5f6593aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-0080009000-4a929d27293cbd8601e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ri-1292035000-9a6b3ebd58995a9b7d10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvr-5291000000-01d2aba3196158f4335cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000009000-226658b31fd18f2f823cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0020009000-823615bf03933229b1cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3092010000-004dd8ecd533328dafebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-4a474af1484b50cf0799Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000000900-4a474af1484b50cf0799Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-0061209100-3708075914e1ec67bb47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-35c39cc16c21189a0e2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000009000-35c39cc16c21189a0e2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-1900617000-44225b83d4d23384c7bcSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected and Quantified0.24 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.27 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.23 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected and Quantified0.26 uMNot AvailablePorcine
    • Barbara U. Metzle...
 details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
DrugBank IDNot Available
HMDB IDHMDB0013341
FooDB IDFDB029401
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24822836
ChEBI ID86223
PubChem Compound ID24779275
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available