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Showing Compound LysoPC(16:0) (FDB027533)

Record Information
Version1.0
Creation date2011-09-21 01:26:02 UTC
Update date2020-09-17 15:39:29 UTC
Primary IDFDB027533
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLysoPC(16:0)
DescriptionLysoPC(16:0/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(16:0/0:0), in particular, consists of one hexadecanoyl chain. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling.
CAS Number14863-27-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphateChEBI
1-16:0-LysoPCChEBI
1-16:0-LysophosphatidylcholineChEBI
1-Hexadecanoyl-2-lysophosphatidylcholineChEBI
1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphocholineChEBI
1-Palmitoyl-2-lysophosphatidylcholineChEBI
1-Palmitoyl-GPCChEBI
1-Palmitoyl-GPC (16:0)ChEBI
1-Palmitoyl-phosphatidylcholineChEBI
1-Palmitoyl-sn-glycero-3-phosphocholineChEBI
1-PalmitoylphosphatidylcholineChEBI
16:0 LYSO-PCChEBI
GPC(16:0)ChEBI
GPC(16:0/0:0)ChEBI
GPCho 16:0/0:0ChEBI
GPCho(16:0/0:0)ChEBI
LPC 16:0/0:0ChEBI
LPC(16:0)ChEBI
LPC(16:0/0:0)ChEBI
LyPC(16:0)ChEBI
LyPC(16:0/0:0)ChEBI
LysoPC 16:0/0:0ChEBI
LysoPC(16:0)ChEBI
Lysophosphatidylcholine(16:0)ChEBI
Lysophosphatidylcholine(16:0/0:0)ChEBI
PC(16:0/0:0)ChEBI
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acidGenerator
1-Palmitoyl-glycero-3-phosphocholineHMDB
1-Palmitoyl-lysophosphatidylcholineHMDB
LysoPC a C16:0HMDB
1-Pam-2-lysoptdchoHMDB
1-Hexadecanoyl-glycero-3-phosphocholineHMDB
1-Palmitoyl-sn-glycerol-3-phosphorylcholineHMDB
1-Palmitoylglycerol-3-phosphorylcholineHMDB
Hydroxide inner salt(S)-isomer OF we 201HMDB
1-O-Hexadecylpropanediol 3-phosphorylcholineHMDB
1-PalmitoyllysophosphatidylcholineHMDB
LYSO-PCHMDB
Hydroxide inner salt(R)-isomer OF we 201HMDB
Hydroxide inner salt(+-)-isomer OF we 201HMDB
Palmitoyl lysophosphatidylcholineHMDB
1-HexadecanoylglycerophosphocholineHMDB
1-PalmitoylglycerophosphocholineHMDB
1-Hexadecanoyl-sn-glycero-3-phosphocholineHMDB
1-Hexadecanoyl-sn-glycerol-3-phosphorylcholineHMDB
1-HexadecanoyllysolecithinHMDB
1-Hexadecyl-sn-glycero-3-phosphocholineHMDB
1-O-Palmitoyl-2-lyso-sn-glycero-3-phosphocholineHMDB
1-O-Palmitoyl-sn-glycero-3-phosphocholineHMDB
1-O-Palmitoyl-sn-glyceryl-3-phosphorylcholineHMDB
1-Palmitoyl-2-lyso-sn-glycero-3-phosphocholineHMDB
1-Palmitoyl-L-alpha-lysophosphatidylcholineHMDB
1-Palmitoyl-L-α-lysophosphatidylcholineHMDB
1-Palmitoyl-sn-glycero-3-phosphorylcholineHMDB
1-Palmitoyl-sn-glycerol-3-phosphatidylcholineHMDB
1-Palmitoyl-sn-glycerol-3-phosphocholineHMDB
1-PalmitoyllecithinHMDB
C(16)-LysophosphatidylcholineHMDB
L-PalmitoyllysolecithinHMDB
L-alpha-LysopalmitoylphosphatidylcholineHMDB
L-alpha-PalmitoyllysophosphatidylcholineHMDB
L-Α-lysopalmitoylphosphatidylcholineHMDB
L-Α-palmitoyllysophosphatidylcholineHMDB
Lysophosphatidylcholine C16:0HMDB
MPPCHMDB
Palmitoyl L-alpha-lysolecithinHMDB
Palmitoyl L-alpha-lysophosphatidylcholineHMDB
Palmitoyl L-lysophosphatidylcholineHMDB
Palmitoyl L-α-lysolecithinHMDB
Palmitoyl L-α-lysophosphatidylcholineHMDB
gamma-Palmitoyl-L-alpha-lysophosphatidylcholineHMDB
Γ-palmitoyl-L-α-lysophosphatidylcholineHMDB
1-Hexadecanoyl-3-glycerophosphorylcholineHMDB
1-Palmitoyl-3-glycerylphosphorylcholineHMDB
1-PalmitoyllysolecithinHMDB
PalmitoyllysolecithinHMDB
Palmitoyllysophosphatidyl cholineHMDB
LysoPC(16:0/0:0)Lipid Annotator, ChEBI
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl ateChEBI
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl ic acidGenerator
1-16:0-LysoatidylcholineChEBI
1-Hexadecanoyl-2-lysoatidylcholineChEBI
1-Hexadecanoyl-sn-glycero-3-ocholineChEBI
1-Palmitoyl-2-lysoatidylcholineChEBI
1-Palmitoyl-atidylcholineChEBI
1-Palmitoyl-glycero-3-ocholineHMDB
1-palmitoyl-glycero-3-phosphocholinehmdb
1-Palmitoyl-lysoatidylcholineHMDB
1-palmitoyl-lysophosphatidylcholinehmdb
1-Palmitoyl-sn-glycero-3-ocholineChEBI
1-PalmitoylatidylcholineChEBI
Lysoatidylcholine(16:0)ChEBI
Lysoatidylcholine(16:0/0:0)ChEBI
Predicted Properties
PropertyValueSource
Water Solubility0.00037 g/LALOGPS
logP1.83ALOGPS
logP1.19ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity142.27 m³·mol⁻¹ChemAxon
Polarizability58.03 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H50NO7P
IUPAC name(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1
InChI KeyASWBNKHCZGQVJV-HSZRJFAPSA-N
Isomeric SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
Average Molecular Weight495.6301
Monoisotopic Molecular Weight495.332489471
Classification
Description Belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLysoPC(16:0), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01y9-9311000000-9632c8a0304eb91f3751Spectrum
Predicted GC-MSLysoPC(16:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLysoPC(16:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 1V, negativesplash10-001i-0010960000-db67de4509c75d7797d52020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-014i-0100190000-466a257c45e674564cc22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-014i-0300490000-fd86cfc8580fd230b8a82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-1000-1900860000-1a2c5a54bd973898558d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0zfr-2901600000-7c35aada431d2e8676522020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0udi-5901100000-be073d1065c18511ab412020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 1V, positivesplash10-0002-0300900000-849ef7d9847d865ee5422020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-0002-0000900000-bd89b3b43b9782d3e5d02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0002-0000900000-7c8338b951da28a32df82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0002-0000900000-aa4c98d730731747150c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0002-0000900000-2d0497b2b78955e2f3732020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0002-0100900000-864a738c4e243f3650a82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0002-0400900000-ce5450f53d5acc84a31e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-000t-0700900000-4ea431cd2258d012bb042020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-0f8a-0900400000-584dbb5e4958e61bcab82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-0f89-0900200000-2b522394881a967d30af2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0f89-0900100000-64234f354a55048175bc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0f89-0900000000-5f827a15f6679c8604602020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0f89-1900000000-f09c6fb5cf772c6435042020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0f89-1900000000-d5bef12c7df660f031a92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0f89-1900000000-f069c0af6b2eb74b93362020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0f89-3900000000-d43ab983a88913d219912020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0f8i-5900000000-2b2fa2819f5e2fce5fe42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0002-0000900000-0b99348189a68c7f55922020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, positivesplash10-0002-0300900000-4249906ba39f9c0a48ea2020-07-22View Spectrum
NMRNot Available
ChemSpider ID405287
ChEMBL IDCHEMBL3093100
KEGG Compound IDC04230
Pubchem Compound ID460602
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10382
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
60 kDa lysophospholipaseASPGQ86U10
Eosinophil lysophospholipaseCLCQ05315
Platelet-activating factor acetylhydrolasePLA2G7Q13093
Platelet-activating factor acetylhydrolase IB subunit gammaPAFAH1B3Q15102
Platelet-activating factor acetylhydrolase IB subunit betaPAFAH1B2P68402
Platelet-activating factor acetylhydrolase 2, cytoplasmicPAFAH2Q99487
Acyl-protein thioesterase 1LYPLA1O75608
Acyl-protein thioesterase 2LYPLA2O95372
Phosphatidylcholine-sterol acyltransferaseLCATP04180
Lysophospholipid acyltransferase 5LPCAT3Q6P1A2
Lysophosphatidylcholine acyltransferase 2LPCAT2Q7L5N7
Pathways
NameSMPDB LinkKEGG Link
Phospholipid BiosynthesisSMP00025 map00564
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference