Record Information
Version1.0
Creation date2011-09-21 00:53:33 UTC
Update date2020-02-24 19:11:11 UTC
Primary IDFDB025161
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePC(16:0/18:0)
DescriptionPC(16:0/18:0) 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(16:0/18:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of stearic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. 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
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility2.2e-05 g/LALOGPS
logP5.62ALOGPS
logP9ChemAxon
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 Count42ChemAxon
Refractivity225.07 m³·mol⁻¹ChemAxon
Polarizability95.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC42H84NO8P
IUPAC name(2-{[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C42H84NO8P/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/h40H,6-39H2,1-5H3/t40-/m1/s1
InChI KeyPZNPLUBHRSSFHT-RRHRGVEJSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC
Average Molecular Weight762.092
Monoisotopic Molecular Weight761.593455181
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
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

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Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPC(16:0/18:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0a4i-0000000490-d88f2a12c72c6e16b54c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-052b-0000000950-8d9dfe7e55c52dab1c772020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0002-0020000910-01911c1e0f87c8e49b152020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-000t-0090000800-80590273ac2914fa2bac2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-053r-0090000200-9b2292a7f9bcea1dc8c92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-053r-0090000100-330d9a7ac1ed8c7dddf52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 73V, negativesplash10-053r-0090000000-ee0d4df936e8eb46d2242020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 91V, negativesplash10-053r-0090000000-4130545053cd0c87703f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 109V, negativesplash10-053r-0090000000-375f7f0bcf027901b6ab2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 134V, negativesplash10-053r-0090000000-1061c43309feed3824662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 158V, negativesplash10-057i-5090000000-e95f748355aa842e15db2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 196V, negativesplash10-004i-9000000000-1a84ff016029161234df2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 53V, negativesplash10-0002-0000000900-6e195caba9da71e7c3742020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-03di-0500000900-95b01663df695379be1f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-001i-0300000900-62c4e365b0fafe8efec92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-03dl-0008900000-be1d0d6b38f1002d172b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-01ox-0109500000-392db28d858abd8bb3152020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 53V, positivesplash10-054k-0000970100-8d9eb2bbec5f813ae4a72020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kkb-0000690700-eaeb1022d870966c83732016-09-19View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bu9-0090000200-7f7015fd1f2dab1557082017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090001000-0fb9ba9bcef10544408b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5i-3090000000-a3206c8150970740995d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-9125bd0d43e31222ebc92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0030000900-a6c60e32bbd2feacba2d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a62-0090000400-36b22ac20ecd43e2bd0e2021-09-22View Spectrum
NMRNot Available
ChemSpider ID24766643
ChEMBL IDNot Available
KEGG Compound IDC00157
Pubchem Compound ID24778686
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB07970
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 IDLecithin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
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