Showing metabocard for LysoPC(16:0/0:0) (BMDB0010382)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:30 UTC
Update Date2020-06-04 20:05:04 UTC
MCDB ID BMDB0010382
Secondary Accession Numbers
  • BMDB0062711
  • BMDB10382
  • BMDB62711
Metabolite Identification
Common NameLysoPC(16:0/0:0)
DescriptionPC(16:0/0:0), also known as 16:0 lyso-PC or 1-palmitoyl-GPC, 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. Thus, PC(16:0/0:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/0:0) exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
Chemical FormulaC24H50NO7P
Average Molecular Weight495.6301
Monoisotopic Molecular Weight495.332489471
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number14863-27-5
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01y9-9311000000-9632c8a0304eb91f37512017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 1V, negativesplash10-001i-0010960000-db67de4509c75d7797d52020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-014i-0100190000-466a257c45e674564cc22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-014i-0300490000-fd86cfc8580fd230b8a82020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-1000-1900860000-1a2c5a54bd973898558d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0zfr-2901600000-7c35aada431d2e8676522020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0udi-5901100000-be073d1065c18511ab412020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 1V, positivesplash10-0002-0300900000-849ef7d9847d865ee5422020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-0002-0000900000-bd89b3b43b9782d3e5d02020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0002-0000900000-7c8338b951da28a32df82020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0002-0000900000-aa4c98d730731747150c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0002-0000900000-2d0497b2b78955e2f3732020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0002-0100900000-864a738c4e243f3650a82020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0002-0400900000-ce5450f53d5acc84a31e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-000t-0700900000-4ea431cd2258d012bb042020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-0f8a-0900400000-584dbb5e4958e61bcab82020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-0f89-0900200000-2b522394881a967d30af2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0f89-0900100000-64234f354a55048175bc2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0f89-0900000000-5f827a15f6679c8604602020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0f89-1900000000-f09c6fb5cf772c6435042020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0f89-1900000000-d5bef12c7df660f031a92020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0f89-1900000000-f069c0af6b2eb74b93362020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0f89-3900000000-d43ab983a88913d219912020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0f8i-5900000000-2b2fa2819f5e2fce5fe42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0002-0000900000-0b99348189a68c7f55922020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, positivesplash10-0002-0300900000-4249906ba39f9c0a48ea2020-07-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-20View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected and Quantified1.00 +/- 0.04 uM details
Detected and Quantified0.97 +/- 0.03 uM details
Detected and Quantified1.20 +/- 0.03 uM details
Detected and Quantified1.25 +/- 0.02 uM details
HMDB IDHMDB0010382
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027533
KNApSAcK IDNot Available
Chemspider ID405287
KEGG Compound IDC04230
BioCyc IDCPD-8343
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound460602
PDB IDNot Available
ChEBI ID72998
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
  2. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.