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Phosphatidylcholine (FDB019141)

Record Information
Version1.0
Creation date2010-04-08 22:14:10 UTC
Update date2020-09-17 15:37:00 UTC
Primary IDFDB019141
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhosphatidylcholine
DescriptionPC(16:0/18:1(9Z)) 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(16:0/18:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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.
CAS Number6753-55-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility2.1e-05 g/LALOGPS
logP5.59ALOGPS
logP8.64ChemAxon
logS-7.6ALOGPS
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 Count41ChemAxon
Refractivity226.18 m³·mol⁻¹ChemAxon
Polarizability94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC42H82NO8P
IUPAC name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1
InChI KeyWTJKGGKOPKCXLL-VYOBOKEXSA-N
Isomeric SMILESCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
Average Molecular Weight760.0761
Monoisotopic Molecular Weight759.577805117
Classification
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
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QqQ 1V, negativesplash10-000t-0090200800-c8db3c4042d858672ebd2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-0006-0020000900-603012fb0ce5ff46f1ea2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 24V, negativesplash10-0udi-0000000190-afc4cd2ac0e64fa396232020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0udl-0000000490-09171592a6955e57e1632020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-0f6x-0000000940-3b9edba3cc0cdfff49452020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0006-0030000910-e80b4b8f6690eea16c9d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-000x-0090000700-527aadfe756a5f2ad9a52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-053r-0090000200-e27632edecd3a83538a42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-053r-0090000000-875a5d38cc2b636df4a12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 72V, negativesplash10-053r-0090000000-6bdad7ea857755dad8df2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 91V, negativesplash10-053r-0090000000-a0160ca0a20b8ca408de2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 109V, negativesplash10-053r-0090000000-d2bc446076d9d86bbadf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 133V, negativesplash10-053r-1090000000-a94d8052959d35d3d25e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 157V, negativesplash10-057i-5190000000-12de950663c450d5ad7f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 194V, negativesplash10-004i-9000000000-906a0ebc0dd0220ac2882020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 53V, negativesplash10-0006-0000000900-0bfd0ce87b7b119d82fb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-0006-0000000900-88f30608c9fd0df934c22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-0006-0000000900-fb159b53855796db7d352020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 34V, negativesplash10-0006-0000000900-084480cec1d6930fa8342020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 41V, negativesplash10-0006-0020000900-103adeac53f8768681222020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 47V, negativesplash10-000x-0090000800-a9198efdf2f4fe5ec5da2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-053r-0090000200-9df170809bae304c6bc12020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-64875131a83d4fda43e62017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000900-dfb450caf9537c97446e2017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fai-1900230300-31ec54e207b217422a2e2017-10-04View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00157
Pubchem Compound IDNot Available
Pubchem Substance ID3457
ChEBI ID49183
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDLRV43-T:LRV43-T
EAFUS ID2000
Dr. Duke IDLECITHIN|PHOSPHATIDYL-CHOLINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1099111
SuperScent IDNot Available
Wikipedia IDPhosphatidylcholine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
CarrotExpected but not quantifiedNot AvailableDUKE, PATHBANK, HMDB
Common peaExpected but not quantifiedNot AvailableDUKE, PATHBANK, HMDB
CucumberExpected but not quantifiedNot AvailableDUKE, PATHBANK, HMDB
SpinachExpected but not quantifiedNot AvailableDUKE, PATHBANK, HMDB
BarleyExpected but not quantifiedNot AvailablePATHBANK, HMDB
BroccoliExpected but not quantifiedNot AvailablePATHBANK, HMDB
DillExpected but not quantifiedNot AvailablePATHBANK, HMDB
EggplantExpected but not quantifiedNot AvailablePATHBANK, HMDB
Garden onionExpected but not quantifiedNot AvailablePATHBANK, HMDB
Garden tomatoExpected but not quantifiedNot AvailablePATHBANK, HMDB
Showing 1 to 10 of 37 entries
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).