Showing metabocard for PG(18:1(9Z)/18:1(9Z)) (BMDB0010634)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:10:45 UTC
Update Date2020-05-20 22:58:54 UTC
BMDB IDBMDB0010634
Secondary Accession Numbers
  • BMDB10634
Metabolite Identification
Common NamePG(18:1(9Z)/18:1(9Z))
DescriptionPG(18:1(9Z)/18:1(9Z)) 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(18:1(9Z)/18:1(9Z)), in particular, consists of two 9Z-octadecenoyl chains at positions C-1 and C-2. 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
1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)ChEBI
1,2-Di-[(9Z)-octadecenoyl]-sn-glycero-3-phospho-(1'-sn-glycerol)ChEBI
1,2-Dioleoyl-sn-3-phosphatidylglycerolChEBI
1,2-Dioleoyl-sn-glycero-3-phosphoglycerolChEBI
PG(18:1/18:1)ChEBI
PG(18:1OMEGA9/18:1OMEGA9)ChEBI
PG(36:2)ChEBI
Phosphatidylglycerol(18:1/18:1)ChEBI
Phosphatidylglycerol(18:1omega9/18:1omega9)ChEBI
Phosphatidylglycerol(36:2)ChEBI
1,2-Dioleoyl-sn-glycero-3-phosphoglycerol, (Z)-isomerMeSH
1,2-DioleoylphosphatidylglycerolMeSH
1,2-Dioleoyl-sn-glycero-3-phospho(1-rac-glycerol)MeSH
1,2-Dioleoyl-sn-glycero-3-phosphoglycerol, (R-(r*,s*))-(Z)-isomerMeSH
DOPGMeSH
Di-C18-1(C)-PGMeSH
1,2-dioleoyl-rac-glycero-3-phosphoglycerolLipid Annotator, HMDB
PG(18:1(9Z)/18:1(9Z))Lipid Annotator
GPG(36:2)Lipid Annotator, HMDB
GPG(18:1/18:1)Lipid Annotator, HMDB
1,2-di(9Z-octadecenoyl)-rac-glycero-3-phosphoglycerolLipid Annotator, HMDB
1,2-di(9Z-octadecenoyl)-rac-glycero-3-phospho-(1'-glycerol)Lipid Annotator, HMDB
GPG(18:1N9/18:1N9)HMDB
GPG(18:1W9/18:1W9)HMDB
PG(18:1N9/18:1N9)HMDB
PG(18:1W9/18:1W9)HMDB
Phosphatidylglycerol(18:1n9/18:1n9)HMDB
Phosphatidylglycerol(18:1W9/18:1W9)HMDB
Chemical FormulaC42H79O10P
Average Molecular Weight775.058
Monoisotopic Molecular Weight774.541085742
IUPAC Name[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional Name(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C42H79O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,39-40,43-44H,3-16,21-38H2,1-2H3,(H,47,48)/b19-17-,20-18-/t39-,40+/m0/s1
InChI KeyDSNRWDQKZIEDDB-SQYFZQSCSA-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 Descriptors
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
logP8.47ALOGPS
logP11.99ChemAxon
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 Count42ChemAxon
Refractivity215.95 m³·mol⁻¹ChemAxon
Polarizability93.13 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 GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056u-4161713900-0edb6e993315b6b70d87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05xu-8294705300-166f0e559fd290f8a699View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i9-9046322000-971789173e215398bfb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01x0-0190311400-9053237cfd3ab8580783View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5390300000-584d168169663f386c1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020100000-b962597174cbf3c00e0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000900-4be40cd8142c638661cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00f0-0190310900-bea2c111bfc5e8ef2641View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-0390310900-b557bf36898428bf0f08View 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 IDHMDB0010634
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027784
KNApSAcK IDNot Available
Chemspider ID24768133
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52927248
PDB IDNot Available
ChEBI ID75385
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available