Record Information
Version1.0
Creation Date2016-09-30 23:48:10 UTC
Update Date2020-06-04 20:44:21 UTC
MCDB ID BMDB0007972
Secondary Accession Numbers
  • BMDB07972
Metabolite Identification
Common NamePC(16:0/18:1(9Z))
DescriptionPC(16:0/18:1(9Z)), also known as PC(16:0/18:1) or 1-POPC, 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. Thus, PC(16:0/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:0/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:0/18:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/18:1(9Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:0/18:1(9Z)) can be biosynthesized from CDP-choline and DG(16:0/18:1(9Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:0/18:1(9Z)) and L-serine can be converted into choline and PS(16:0/18:1(9Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(16:0/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/18:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/18:1(9Z)) pathway.
Structure
Thumb
Synonyms
ValueSource
1-16:0-2-18:1-PhosphatidylcholineChEBI
1-Hexadecanoyl-2-oleoyl-sn-glycero-3-phosphocholineChEBI
1-Palmitoyl-2-oleoyl-GPCChEBI
1-Palmitoyl-2-oleoyl-GPC (16:0/18:1)ChEBI
1-Palmitoyl-2-oleoyl-lecithinChEBI
1-Palmitoyl-2-oleoylphosphatidylcholineChEBI
1-Palmotoyl-2-oleoylglycero-3-phosphocholineChEBI
1-POPCChEBI
16:0-18:1-PCChEBI
GPC(16:0/18:1)ChEBI
GPCho(16:0/18:1)ChEBI
GPCho(16:0/18:1omega9)ChEBI
GPCho(34:1)ChEBI
LecithinChEBI
PalmitoyloleoylphosphatidylcholineChEBI
PC(16:0/18:1)ChEBI
PC(16:0/18:1omega9)ChEBI
PC(34:1)ChEBI
Phosphatidylcholine(16:0/18:1)ChEBI
Phosphatidylcholine(16:0/18:1omega9)ChEBI
Phosphatidylcholine(34:1)ChEBI
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylcholineMeSH
alpha-Phosphatidylcholine-beta-oleoyl-gamma-palmitoylMeSH
1-Palmitoyl-2-oleoyl-phosphatidylcholineMeSH
1-Palmitoyl-2-oleoylphosphatidylcholine, (R)-(Z)-isomerMeSH
POPC LipidMeSH
beta-Oleoyl-gamma-palmitoyl-L-alpha-phosphatidylcholineMeSH
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholineLipid Annotator, MeSH, HMDB
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
PC(16:0/18:1(9Z))Lipid Annotator, ChEBI
1-Palmitoyl-2-oleoyl-3-sn-phosphatidylcholineHMDB
1-Palmitoyl-2-oleoyl-L-alpha-lecithinHMDB
1-Palmitoyl-2-oleoyl-L-alpha-phosphatidylcholineHMDB
1-Palmitoyl-2-oleoyl-L-α-lecithinHMDB
1-Palmitoyl-2-oleoyl-L-α-phosphatidylcholineHMDB
1-Palmitoyl-2-oleoyl-sn-3-phosphocholineHMDB
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphorylcholineHMDB
1-Palmitoyl-2-oleoyl-sn-glycero-phosphatidylcholineHMDB
1-Palmitoyl-2-oleoyl-sn-glycero-phosphocholineHMDB
1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphatidylcholineHMDB
1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholineHMDB
1-Palmitoyl-2-oleoyl-sn-glyceryl-3-phosphorylcholineHMDB
1-Palmitoyl-2-oleoyllecithinHMDB
1-Palmitoyl-2-oleyl-3-sn-phosphatidylcholineHMDB
2-Oleo-1-palmitin phosphate choline esterHMDB
2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholineHMDB
2-Oleoyl-1-palmitoyllecithinHMDB
GPC(16:0/18:1(9Z))HMDB
GPC(16:0/18:1n9)HMDB
GPC(16:0/18:1w9)HMDB
GPC(34:1)HMDB
GPCho(16:0/18:1(9Z))HMDB
GPCho(16:0/18:1n9)HMDB
GPCho(16:0/18:1w9)HMDB
L-1-Palmitoyl-2-oleoylphosphatidylcholineHMDB
L-PalmitoyloleoylphosphatidylcholineHMDB
L-alpha-1-Palmitoyl-2-oleoylphosphatidylcholineHMDB
L-α-1-Palmitoyl-2-oleoylphosphatidylcholineHMDB
PC(16:0/18:1n9)HMDB
PC(16:0/18:1w9)HMDB
POPCHMDB
Phosphatidylcholine(16:0/18:1(9Z))HMDB
Phosphatidylcholine(16:0/18:1n9)HMDB
Phosphatidylcholine(16:0/18:1w9)HMDB
β-Oleoyl-γ-palmitoyl-L-α-phosphatidylcholineHMDB
Chemical FormulaC42H82NO8P
Average Molecular Weight760.0761
Monoisotopic Molecular Weight759.577805117
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number6753-55-5
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, negativesplash10-000t-0090200800-c8db3c4042d858672ebd2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-0006-0020000900-603012fb0ce5ff46f1ea2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 24V, negativesplash10-0udi-0000000190-afc4cd2ac0e64fa396232020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0udl-0000000490-09171592a6955e57e1632020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 36V, negativesplash10-0f6x-0000000940-3b9edba3cc0cdfff49452020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, negativesplash10-0006-0030000910-e80b4b8f6690eea16c9d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, negativesplash10-000x-0090000700-527aadfe756a5f2ad9a52020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 54V, negativesplash10-053r-0090000200-e27632edecd3a83538a42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-053r-0090000000-875a5d38cc2b636df4a12020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 72V, negativesplash10-053r-0090000000-6bdad7ea857755dad8df2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 91V, negativesplash10-053r-0090000000-a0160ca0a20b8ca408de2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, negativesplash10-053r-0090000000-d2bc446076d9d86bbadf2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 133V, negativesplash10-053r-1090000000-a94d8052959d35d3d25e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 157V, negativesplash10-057i-5190000000-12de950663c450d5ad7f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 194V, negativesplash10-004i-9000000000-906a0ebc0dd0220ac2882020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 53V, negativesplash10-0006-0000000900-0bfd0ce87b7b119d82fb2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-0006-0000000900-88f30608c9fd0df934c22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-0006-0000000900-fb159b53855796db7d352020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, negativesplash10-0006-0000000900-084480cec1d6930fa8342020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 41V, negativesplash10-0006-0020000900-103adeac53f8768681222020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 47V, negativesplash10-000x-0090000800-a9198efdf2f4fe5ec5da2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, negativesplash10-053r-0090000200-9df170809bae304c6bc12020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-64875131a83d4fda43e62017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0600000900-dfb450caf9537c97446e2017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fai-1900230300-31ec54e207b217422a2e2017-10-04View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified17.0 +/- 0.2 uM details
Detected and Quantified22 +/- 1 uM details
Detected and Quantified26 +/- 1 uM details
Detected and Quantified16.1 +/- 0.5 uM details
HMDB IDHMDB0007972
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030200
KNApSAcK IDNot Available
Chemspider ID4593686
KEGG Compound IDNot Available
BioCyc IDCPD-8157
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5497103
PDB IDNot Available
ChEBI ID73001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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.