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Showing Compound PC(18:0/18:0) (FDB025227)

Record Information
Version1.0
Creation date2011-09-21 00:54:22 UTC
Update date2020-02-24 19:11:11 UTC
Primary IDFDB025227
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePC(18:0/18:0)
DescriptionPC(18:0/18:0) 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(18:0/18:0), in particular, consists of two chains of stearic acid at the C-1 and C-2 positions. The stearic acid moieties are 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 Number816-94-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility2.2e-05 g/LALOGPS
logP5.92ALOGPS
logP9.89ChemAxon
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 Count44ChemAxon
Refractivity234.27 m³·mol⁻¹ChemAxon
Polarizability99.02 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC44H88NO8P
IUPAC name(2-{[(2R)-2,3-bis(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C44H88NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h42H,6-41H2,1-5H3/t42-/m1/s1
InChI KeyNRJAVPSFFCBXDT-HUESYALOSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC
Average Molecular Weight790.1452
Monoisotopic Molecular Weight789.624755309
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:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 31V, negativesplash10-0089-0000000590-0aad18afe34a7c3e4d4c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 39V, negativesplash10-00e9-0000000950-0e01653ba450f4cf24742020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 45V, negativesplash10-00e9-0030000910-5f5f6ea7c69c11446a372020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 52V, negativesplash10-0089-0090000600-450dc346ec045426f41a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 58V, negativesplash10-001i-0090000200-ac0ebb03ecad4a7553522020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 64V, negativesplash10-001i-0090000000-0cda3c7a3fd1efdab6602020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 78V, negativesplash10-001i-0090000000-8039839adbbb06bce8cc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 97V, negativesplash10-001i-0090000000-32180842465e1f0ca0622020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 118V, negativesplash10-001i-0090000000-add4cfd543c3c75001502020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 143V, negativesplash10-001i-1090000000-731977fa0efe340b2c9b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 170V, negativesplash10-003r-6090000000-10e012ff7fe106b8a5f02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 210V, negativesplash10-004i-9000000000-003f91760dbf6d21ebe72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-00di-0000000900-ed2638f28be0dc4467832020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-0006-0000000900-08c46febfbe4ee7625932020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 34V, positivesplash10-000x-0600000900-f13e1162895079b395812020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 48V, positivesplash10-001i-0900000000-095cbcd6f3947470459d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 74V, positivesplash10-001i-0900000000-b0b68022ed94da51246c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 99V, positivesplash10-001i-2900000000-552209425d26c02a04762020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 124V, positivesplash10-008i-6900000000-b39bf3dd8da792e301232020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 161V, positivesplash10-0079-9600000000-6622c8393c18efd1dd282020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 198V, positivesplash10-007a-9400000000-a1be01e41d76c34ddef82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 236V, positivesplash10-0072-9200000000-df8e8bf2dc44c5e36e282020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-ddeff1f077816b130f0b2017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0600000900-cbf5b5700da15bd27faf2017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900021300-9f90c5ee485e939b0d382017-10-04View Spectrum
NMRNot Available
ChemSpider ID85004
ChEMBL IDNot Available
KEGG Compound IDC00157
Pubchem Compound ID94190
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB08036
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDPC1
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