Showing metabocard for PG(16:1(9Z)/20:3(5Z,8Z,11Z)) (BMDB0010593)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:09:55 UTC
Update Date2020-05-11 19:12:17 UTC
BMDB IDBMDB0010593
Secondary Accession Numbers
  • BMDB10593
Metabolite Identification
Common NamePG(16:1(9Z)/20:3(5Z,8Z,11Z))
DescriptionPG(16:1(9Z)/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(16:1(9Z)/20:3(5Z,8Z,11Z)), in particular, consists of one 9Z-hexadecenoyl 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
Phosphatidylglycerol(16:1/20:3)HMDB
Phosphatidylglycerol(36:4)HMDB
PG(36:4)HMDB
GPG(16:1/20:3)HMDB
1-(9Z-Hexadecenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phospho-(1'-glycerol)HMDB
1-Palmitoleoyl-2-meadoyl-sn-glycero-3-phosphoglycerolHMDB
PG(16:1/20:3)HMDB
1-(9Z-Hexadecenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphoglycerolHMDB
GPG(36:4)HMDB
PG(16:1(9Z)/20:3(5Z,8Z,11Z))Lipid Annotator
Chemical FormulaC42H75O10P
Average Molecular Weight771.0127
Monoisotopic Molecular Weight770.509785132
IUPAC Name[(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphinic acid
Traditional Name(2S)-2,3-dihydroxypropoxy(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C42H75O10P/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-42(46)52-40(38-51-53(47,48)50-36-39(44)35-43)37-49-41(45)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h14,16-18,20,22,26,28,39-40,43-44H,3-13,15,19,21,23-25,27,29-38H2,1-2H3,(H,47,48)/b16-14-,18-17-,22-20-,28-26-/t39-,40+/m0/s1
InChI KeyVWDLPQNBLHJJIU-OILVUHFKSA-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
logP7.98ALOGPS
logP11.27ChemAxon
logS-6.9ALOGPS
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 Count40ChemAxon
Refractivity218.18 m³·mol⁻¹ChemAxon
Polarizability90.84 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, Positivesplash10-0fy9-3091431600-fcab5f2eb20b8b3c3670View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-4191221100-d68a1774e02bcfd1ba2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a71-6192121000-d2abb41ae70bf1590b66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-0192200300-78664dd0e45eb7323655View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ug0-5291100000-00c6bf8750376be4134eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020000000-1736ad592537855d5d79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000900-c28bac06e088565afc8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-10k9-0179320700-838be3e054b3996aa128View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-10k9-0279320700-3ad2dd6c75bd1a51c1b6View 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 IDHMDB0010593
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24768092
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480607
PDB IDNot Available
ChEBI ID89071
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available