Showing metabocard for PC(16:0/16:0) (BMDB0000564)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:32:52 UTC
Update Date2020-06-04 20:04:17 UTC
MCDB ID BMDB0000564
Secondary Accession Numbers
  • BMDB00564
Metabolite Identification
Common NamePC(16:0/16:0)
DescriptionPC(16:0/16:0), also known as DPPC or 16:0-16:0-PC, 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(16:0/16:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/16:0) exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. PC(16:0/16:0) exists in all eukaryotes, ranging from yeast to humans. In cattle, PC(16:0/16:0) is involved in the metabolic pathway called phospholipid biosynthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Bis(hexadecanoyl)-sn-glycero-3-phosphocholineChEBI
1,2-Dipalmitoyl-L-lecithinChEBI
1,2-Dipalmitoyl-sn-glycero-3-phosphatidylcholineChEBI
1,2-Dipalmitoyl-sn-glycero-3-phosphocholineChEBI
1,2-DipalmitoylphosphatidylcholineChEBI
1-16:0-2-16:0-PhosphatidylcholineChEBI
16:0-16:0-PCChEBI
Colfosceril palmitateChEBI
Colfoscerili palmitasChEBI
Dipalmitoyl phosphatidylcholineChEBI
Dipalmitoyl-GPCChEBI
DipalmitoylphosphatidylcholineChEBI
GPC(16:0/16:0)ChEBI
GPCho 16:0/16:0ChEBI
GPCho(16:0/16:0)ChEBI
Palmitate de colfoscerilChEBI
Palmitato de colfosceriloChEBI
PC 16:0/16:0ChEBI
PC(32:0)ChEBI
Phosphatidylcholine 16:0/16:0ChEBI
Phosphatidylcholine(16:0/16:0)ChEBI
Phosphatidylcholine(32:0)ChEBI
Colfosceril palmitic acidGenerator
Palmitic acid de colfoscerilGenerator
1,2-Dipalmitoyl-rac-glycero-3-phosphocholineHMDB
LecithinHMDB
1,2-Dihexadecanoyl-rac-glycero-3-phosphocholineHMDB
GPCho(32:0)HMDB
(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide hydroxide inner saltHMDB
(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide inner saltHMDB
1,2-Bis(palmitoyl)-sn-glycero-3-phosphocholineHMDB
1,2-Dihexadecanoyl-sn-glycerol-3-phosphorylcholineHMDB
1,2-Dipalmitoyl-3-sn-phosphatidylcholineHMDB
1,2-Dipalmitoyl-L-3-phosphatidylcholineHMDB
1,2-Dipalmitoyl-L-a-lecithinHMDB
1,2-Dipalmitoyl-L-a-phosphatidylcholineHMDB
1,2-Dipalmitoyl-L-alpha-lecithinHMDB
1,2-Dipalmitoyl-L-alpha-phosphatidylcholineHMDB
1,2-Dipalmitoyl-L-phosphatidylcholineHMDB
1,2-Dipalmitoyl-sn-3-glycerophosphocholineHMDB
1,2-Dipalmitoyl-sn-glycero-3-phosphorylcholineHMDB
1,2-Dipalmitoyl-sn-glycerol-3-phosphocholineHMDB
1,2-Dipalmitoyl-sn-glycerophosphocholineHMDB
1,2-Dipalmitoyl-sn-glycerophosphorylcholineHMDB
1,2-Dipalmitoyl-sn-glyceryl-3-phosphocholineHMDB
1,2-Dipalmitoyl-sn-phosphatidylcholineHMDB
1,2-Dipalmitoylglycero-3-phosphocholineHMDB
1,2-L-a-DipalmitoylphosphatidylcholineHMDB
1,2-L-alpha-DipalmitoylphosphatidylcholineHMDB
b,g-Dipalmitoyl L-a-phosphatidylcholineHMDB
b,g-Dipalmitoyl L-alpha-phosphatidylcholineHMDB
b,g-Dipalmitoyl-L-(a)-lecithinHMDB
b,g-Dipalmitoyl-L-phosphatidylcholineHMDB
Dihexadecanoyl-sn-glycero-3-phosphocholineHMDB
Dipalmitoyl L-a-phosphatidylcholineHMDB
Dipalmitoyl L-alpha-phosphatidylcholineHMDB
Dipalmitoyl-L-3-glycerylphosphorylcholineHMDB
Dipalmitoyl-L-a-lecithinHMDB
Dipalmitoyl-L-a-phosphatidylcholineHMDB
Dipalmitoyl-L-alpha-lecithinHMDB
Dipalmitoyl-L-alpha-phosphatidylcholineHMDB
Dipalmitoyl-sn-3-phosphatidylcholineHMDB
DPPCHMDB
L-1,2-Dipalmitoyl-a-lecithinHMDB
L-1,2-Dipalmitoyl-alpha-lecithinHMDB
L-1,2-DipalmitoylphosphatidylcholineHMDB
L-a-1,2-Dipalmitoyl lecithinHMDB
L-a-DipalmitoylecithinHMDB
L-a-DipalmitoyllecithinHMDB
L-a-DipalmitoylphosphatidylcholineHMDB
L-a-DPPCHMDB
L-alpha-1,2-Dipalmitoyl lecithinHMDB
L-alpha-DipalmitoylecithinHMDB
L-alpha-DipalmitoyllecithinHMDB
L-alpha-DipalmitoylphosphatidylcholineHMDB
L-alpha-DPPCHMDB
L-b,g-Dipalmitoyl-a-lecithinHMDB
L-b,g-Dipalmitoyl-a-phosphatidylcholineHMDB
L-b,g-Dipalmitoyl-alpha-lecithinHMDB
L-b,g-Dipalmitoyl-alpha-phosphatidylcholineHMDB
L-b,g-DipalmitoylphosphatidylcholineHMDB
L-Dipalmitoyl lecithinHMDB
L-DPPCHMDB
PC Aa C32:0HMDB
sn-3-DipalmitoyllecithinHMDB
1,2-Dipalmitoyl-GPCHMDB
PC(16:0/16:0)Lipid Annotator
1,2-Distearoyl-glycero-3-phosphocholineHMDB
Chemical FormulaC40H80NO8P
Average Molecular Weight734.0389
Monoisotopic Molecular Weight733.562155053
IUPAC Name(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number63-89-8
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1
InChI KeyKILNVBDSWZSGLL-KXQOOQHDSA-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
logP5.29ALOGPS
logP8.11ChemAxon
logS-7.5ALOGPS
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 Count40ChemAxon
Refractivity215.87 m³·mol⁻¹ChemAxon
Polarizability92 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 - IT 40V, negativesplash10-066r-0060100900-b6bff2ff205808890e0b2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-001i-0900000000-455598e8d7de92b66a2d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-0udi-0000290000-79bb58a12a550b7285842020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-001i-0900000400-ed1d6ef09691e9bb1b3e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-001i-0000000900-012345aef55bfeb672012020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-004j-0000900000-208fe5d1fc5dcb9e17872020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-0002-0000029000-0cc983f3015a15000bcb2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, positivesplash10-001r-0000000900-fa22d7b44b6ecf7bf3cb2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-001i-0500000900-6608b50815a9b5d35f042020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 51V, positivesplash10-001i-0900000000-9afadd11d3d3f123032d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 68V, positivesplash10-001i-2900000000-ce1e31a52e9cb1245e692020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 85V, positivesplash10-001r-4900000000-d399948e3d53f292acf42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 124V, positivesplash10-0079-9800000000-58fcb9ea0920120df2542020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 137V, positivesplash10-0079-9700000000-1bd1b9fb29d82e116b292020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 162V, positivesplash10-007a-9600000000-f4a52586e5510140e9942020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 189V, positivesplash10-0072-9400000000-494bd7a2e515e6c62d172020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 223V, positivesplash10-0002-9100000000-548cf59f4be7b55dd9422020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 258V, positivesplash10-0002-9000000000-852b94593bcfb0db899c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 309V, positivesplash10-0002-9000000000-1c426c57d21ff7447e742020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-002k-0000900200-dfdc7f3a135b074862482020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-014i-0000900000-875312e72ac68920d8df2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-01q9-0980000000-e120b0535f2910e5dbe82020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-e904df388d2d70397c9f2017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-18b2f9e577dc5a9bfcb82017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900211200-e76cb9b9e105ad69b5702017-10-04View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not Available2012-12-04View 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
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified10.4 +/- 0.4 uM details
Detected and Quantified12.5 +/- 0.5 uM details
Detected and Quantified15.1 +/- 0.3 uM details
Detected and Quantified10.2 +/- 0.3 uM details
HMDB IDHMDB0000564
DrugBank IDDB09114
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022121
KNApSAcK IDNot Available
Chemspider ID398235
KEGG Compound IDC00157
BioCyc ID1-2-DIPALMITOYLPHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5548
PubChem Compound452110
PDB IDNot Available
ChEBI ID72999
References
Synthesis ReferenceBouirig, H.; Eloy, D.; Jardon, P. Formation and reactivity of the singlet oxygen photosensitized by hypericin in the liposomes of dipalmitoylphosphatidylcholine. Evidence of delayed oxidation. Journal de Chimie Physique et de Physico-Chimie Biologique (1992), 89(6), 1391-411.
Material Safety Data Sheet (MSDS)Download (PDF)
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.