Showing metabocard for PC(18:1(9Z)/18:1(9Z)) (BMDB0000593)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:33:17 UTC
Update Date2020-06-04 20:44:40 UTC
MCDB ID BMDB0000593
Secondary Accession Numbers
  • BMDB00593
Metabolite Identification
Common NamePC(18:1(9Z)/18:1(9Z))
DescriptionPC(18:1(9Z)/18:1(9Z)) , also known as dielaidinoyl lecithin or 1,2-DOCPC, 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. PC(18:1(9Z)/18:1(9Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(R-(Z,Z))-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxideChEBI
1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineChEBI
1,2-Dioleoyl-L-alpha-lecithinChEBI
1-(9Z)-Octadecenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineChEBI
1-C18:1(Omega-9)-2-C18:1(omega-9)-phosphatidylcholineChEBI
Dioleoyl lecithinChEBI
Dioleoyl phosphatidylcholineChEBI
PC 18:1ChEBI
PC(18:1(9Z)/18:1(9Z))ChEBI
PC(18:1/18:1)ChEBI
Phosphatidylcholine 18:1ChEBI
1,2-Dioleoyl-L-a-lecithinGenerator
1,2-Dioleoyl-L-α-lecithinGenerator
1,2-Di-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineHMDB
1,2-Dioleoyl-sn-glycerol-3-ethylphosphocholineMeSH
DioleylphosphatidylcholineMeSH
1,2-Oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomerMeSH
DielaidoylphosphatidylcholineMeSH
DioleoylphosphatidylcholineMeSH
1,2-DioleoylglycerophosphocholineMeSH
1,2-Oleoyl-sn-glycero-3-phosphocholineMeSH
DOPCMeSH
Dielaidinoyl lecithinMeSH
1,2-DOCPCMeSH
1,2-Dioleoyl glycerophosphocholineMeSH
1,2-Dioleoyl-sn-glycero-3-phosphocholineMeSH
1,2-OleoylphosphatidylcholineMeSH
1,2-Dioleoyl-GPCHMDB
1,2-Dioleoyl-sn-glycero-phosphatidylcholineHMDB
GPC(18:1(9Z)/18:1(9Z))HMDB
GPC(18:1/18:1)HMDB
GPC(18:1n9/18:1n9)HMDB
GPC(18:1w9/18:1w9)HMDB
GPC(36:2)HMDB
GPCho(18:1(9Z)/18:1(9Z))HMDB
GPCho(18:1/18:1)HMDB
GPCho(18:1n9/18:1n9)HMDB
GPCho(18:1w9/18:1w9)HMDB
GPCho(36:2)HMDB
PC(18:1n9/18:1n9)HMDB
PC(18:1w9/18:1w9)HMDB
PC(36:2)HMDB
Phosphatidylcholine(18:1(9Z)/18:1(9Z))HMDB
Phosphatidylcholine(18:1/18:1)HMDB
Phosphatidylcholine(18:1n9/18:1n9)HMDB
Phosphatidylcholine(18:1w9/18:1w9)HMDB
Phosphatidylcholine(36:2)HMDB
1,2-Dioleoyl-3-sn-phosphatidylcholineHMDB
1,2-Dioleoyl-sn-glycero-3-phosphochlineHMDB
1,2-Dioleoyl-sn-glycero-3-phosphorylcholineHMDB
1,2-Dioleoyl-sn-phosphatidylcholineHMDB
1,2-DioleoylphosphatidylcholineHMDB
1,2-Dioleyl-L-lecithinHMDB
Dioleoyl L-alpha-lecithinHMDB
Dioleoyl L-α-lecithinHMDB
Dioleoyl-3-sn-phosphatidylcholineHMDB
Dioleoyl-L-alpha-glycerophosphocholineHMDB
Dioleoyl-L-alpha-glycerophosphorylcholineHMDB
Dioleoyl-L-alpha-phosphatidylcholineHMDB
Dioleoyl-L-α-glycerophosphocholineHMDB
Dioleoyl-L-α-glycerophosphorylcholineHMDB
Dioleoyl-L-α-phosphatidylcholineHMDB
DioleoyllecithinHMDB
L-Dioleoyl lecithinHMDB
L-DioleoylphosphatidylcholineHMDB
L-alpha-Di(cis-9-octadecanoyl) lecithinHMDB
L-alpha-Dioleoyl phosphatidylcholineHMDB
L-alpha-DioleoyllecithinHMDB
L-alpha-DioleylphosphatidylcholineHMDB
L-α-Di(cis-9-octadecanoyl) lecithinHMDB
L-α-Dioleoyl phosphatidylcholineHMDB
L-α-DioleoyllecithinHMDB
L-α-DioleylphosphatidylcholineHMDB
sn-3-DioleoyllecithinHMDB
1,2-Dioleoylglycerol-3-phosphorylcholineHMDB
1,2-Dioleoylglyceryl-3-phosphorylcholineHMDB
1,2-DioleoyllecithinHMDB
DioleoylglycerophosphocholineHMDB
DioleoylglycerophosphorylcholineHMDB
DioleoylglycerylphosphorylcholineHMDB
Dioleyl lecithinHMDB
Dioleyl phosphatidylcholineHMDB
Chemical FormulaC44H84NO8P
Average Molecular Weight786.1134
Monoisotopic Molecular Weight785.593455181
IUPAC Name(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number68737-67-7
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C44H84NO8P/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/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1
InChI KeySNKAWJBJQDLSFF-NVKMUCNASA-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
logP5.78ALOGPS
logP9.17ChemAxon
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 Count42ChemAxon
Refractivity236.5 m³·mol⁻¹ChemAxon
Polarizability96.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-36f689a3cf8b031c9ce52017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-4df68b8e85813f4b5ad82017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900021300-f15a88b3adc3a38193cb2017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-53a8e01f33b2af13f2262021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000190-64f46bdfe255d6a5b5e42021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004k-0900139110-7365097ffb2d5d55b4342021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-64c382f846ba04194d312021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-6c06686879d9f7790e622021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0200249400-1ae2411ef15a63cb3b2d2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-e54f4b7d729e27672b372021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-3a2440aaca7e87ec13a52021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900021300-24d60344b49a468b04692021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-23df8d3c4971511f3b912021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0050030900-b121f3ff4b078b5df33e2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1090200000-673c166236d767f9289e2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-683d2aaf9f12a9d086142021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0010000090-37042360a3899f1fdc232021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00f0-0090000090-06eeedb644af6eeff7ec2021-09-25View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified5.82 +/- 0.04 uM details
Detected and Quantified7.0 +/- 0.2 uM details
Detected and Quantified9.5 +/- 0.1 uM details
Detected and Quantified5.48 +/- 0.03 uM details
HMDB IDHMDB0062690
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8525772
KEGG Compound IDNot Available
BioCyc IDCPD-2181
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10350317
PDB IDNot Available
ChEBI ID74669
References
Synthesis ReferenceTokuyama, Satoru; Morisawa, Kazuya; Nakachi, Osamu; Nakano, Yoshiro; Miki, Tomoharu. Preparation of phosphatidylcholines. Jpn. Kokai Tokkyo Koho (1989), 6 pp.
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.