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Showing Compound PC(o-22:2(13Z,16Z)/22:2(13Z,16Z)) (FDB029455)

Record Information
Version1.0
Creation date2011-09-21 01:56:07 UTC
Update date2019-11-26 03:21:31 UTC
Primary IDFDB029455
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePC(o-22:2(13Z,16Z)/22:2(13Z,16Z))
DescriptionPC(o-22:2(13Z,16Z)/22:2(13Z,16Z)) 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-22:2(13Z,16Z)/22:2(13Z,16Z)), in particular, consists of one chain of Docosadienyl alcohol at the C-1 position and one chain of docosadienoic acid at the C-2 position. The Docosadienyl alcohol moiety is derived from animal fat, while the docosadienoic acid moiety is derived from 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility2.4e-05 g/LALOGPS
logP7.09ALOGPS
logP12.38ChemAxon
logS-7.6ALOGPS
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 Count48ChemAxon
Refractivity275.79 m³·mol⁻¹ChemAxon
Polarizability111.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC52H98NO7P
IUPAC name(2-{[(2R)-3-[(13Z,16Z)-docosa-13,16-dien-1-yloxy]-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C52H98NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h14-17,20-23,51H,6-13,18-19,24-50H2,1-5H3/b16-14-,17-15-,22-20-,23-21-/t51-/m1/s1
InChI KeyGCAMFMBVIXVYSA-VIVKCUGUSA-N
Isomeric SMILESCCCCC\C=C/C\C=C/CCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC
Average Molecular Weight880.3108
Monoisotopic Molecular Weight879.708091007
Classification
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
Physiological effect

Organoleptic effect:

Disposition

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Naturally occurring process:

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Industrial application:

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Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-0007000290-46109b57eace9c21f25f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2019200630-6b82709f5d224509f1942017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-009i-4019200000-69e87fa349b9f78b19ff2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000090-28c0ee1b28fef89e85882021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-0004001090-f15ee5c76297b3cfb7452021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-4009400000-c0a396c92ae9a9408abe2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000009-f52b9a9681edddda0ddf2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000000009-f52b9a9681edddda0ddf2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue0-0007120191-4ce8fbe2ae6ea98b6fb12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-9107032230-fd221ac76a433bc194042017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cei-4209021100-31819aa8a85dc752f6fc2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06s9-7009004210-9128766be59fc0493e6d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-03f6106a76b0f10572b32021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000090-03f6106a76b0f10572b32021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900061070-e6a838e80bb30c5167772021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481765
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13455
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Cow milk, pasteurized, vitamin A + D added, 0% fat0.03600 - 0.03600 uM0.03600 uMEXPERIMENTAL
Cow milk, pasteurized, vitamin A + D added, 1% fat0.02400 - 0.02400 uM0.02400 uMEXPERIMENTAL
Cow milk, pasteurized, vitamin A + D added, 2% fat0.03000 - 0.03000 uM0.03000 uMEXPERIMENTAL
Cow milk, pasteurized, vitamin D added, 3.25% fat0.02800 - 0.02800 uM0.02800 uMEXPERIMENTAL
Milk (Cow)0.04100 - 0.04100 uM0.04100 uM30994344
AnatidaeExpected but not quantifiedNot AvailableHMDB
BeefaloExpected but not quantifiedNot AvailableHMDB
BisonExpected but not quantifiedNot AvailableHMDB
BuffaloExpected but not quantifiedNot AvailableHMDB
Cattle (Beef, Veal)Expected but not quantifiedNot AvailableHMDB
Showing 1 to 10 of 34 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference