Showing metabocard for PG(18:0/20:3(5Z,8Z,11Z)) (BMDB0010608)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:10:13 UTC
Update Date2020-05-11 19:12:30 UTC
BMDB IDBMDB0010608
Secondary Accession Numbers
  • BMDB10608
Metabolite Identification
Common NamePG(18:0/20:3(5Z,8Z,11Z))
DescriptionPG(18:0/20:3(5Z,8Z,11Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(18:0/20:3(5Z,8Z,11Z)), in particular, consists of one octadecanoyl chain to the C-1 atom, and one 5Z,8Z,11Z-eicosatrienoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Octadecanoyl-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phospho-(1'-glycerol)HMDB
1-Stearoyl-2-meadoyl-sn-glycero-3-phosphoglycerolHMDB
GPG(18:0/20:3)HMDB
GPG(18:0/20:3N9)HMDB
GPG(18:0/20:3W9)HMDB
GPG(38:3)HMDB
PG(18:0/20:3)HMDB
PG(18:0/20:3N9)HMDB
PG(18:0/20:3W9)HMDB
PG(38:3)HMDB
Phosphatidylglycerol(18:0/20:3)HMDB
Phosphatidylglycerol(18:0/20:3n9)HMDB
Phosphatidylglycerol(18:0/20:3W9)HMDB
Phosphatidylglycerol(38:3)HMDB
1-Octadecanoyl-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphoglycerolHMDB
PG(18:0/20:3(5Z,8Z,11Z))Lipid Annotator
Chemical FormulaC44H81O10P
Average Molecular Weight801.0817
Monoisotopic Molecular Weight800.556735324
IUPAC Name[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-(octadecanoyloxy)propoxy]phosphinic acid
Traditional Name(2S)-2,3-dihydroxypropoxy(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-(octadecanoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C44H81O10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-44(48)54-42(40-53-55(49,50)52-38-41(46)37-45)39-51-43(47)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h17,19,22,24,28,30,41-42,45-46H,3-16,18,20-21,23,25-27,29,31-40H2,1-2H3,(H,49,50)/b19-17-,24-22-,30-28-/t41-,42+/m0/s1
InChI KeyHYLAOFWJHGFMIV-JKLLYNSPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct ParentPhosphatidylglycerols
Alternative Parents
Substituents
  • 1,2-diacylglycerophosphoglycerol
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.77ALOGPS
logP12.52ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area148.82 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity226.26 m³·mol⁻¹ChemAxon
Polarizability97.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fwi-3091321420-0eb5363b4b28206e7dafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05s0-4192211300-19afabe84f86c8624e22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-7094202100-23c1bb348f51d61090bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-1192110400-7326990e6a628d490674View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-5290100100-5aa35d3d8382863ab90bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020000000-426350e4fba033ecc78eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-2af1498ed72bccbc9bfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053s-0199440900-b607668234f0f66c0d5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a62-0399440900-ffdea174b18076492748View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010608
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027758
KNApSAcK IDNot Available
Chemspider ID24768107
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480611
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available