Showing metabocard for PGP(18:1(9Z)/20:3(5Z,8Z,11Z)) (BMDB0096766)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-03-25 16:10:56 UTC
Update Date2020-05-11 19:22:19 UTC
BMDB IDBMDB0096766
Secondary Accession NumbersNone
Metabolite Identification
Common NamePGP(18:1(9Z)/20:3(5Z,8Z,11Z))
DescriptionPGP(18:1(9Z)/20:3(5Z,8Z,11Z)) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(18:1(9Z)/20:3(5Z,8Z,11Z)), in particular, consists of one 9Z-octadecenoyl chain to the C-1 atom, and one 5Z,8Z,11Z-eicosatrienoyl to the C-2 atom. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PGP(38:4)Lipid Annotator, HMDB
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acidLipid Annotator, HMDB
1-oleoyl-2-meadoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
PGP(18:1(9Z)/20:3(5Z,8Z,11Z))Lipid Annotator
1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
PGP(18:1/20:3)Lipid Annotator, HMDB
PGP(18:1n9/20:3n9)HMDB
PGP(18:1W9/20:3W9)HMDB
Chemical FormulaC44H80O13P2
Average Molecular Weight879.0457
Monoisotopic Molecular Weight878.50741567
IUPAC Name[(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid
Traditional Name(2S)-2-hydroxy-3-{[hydroxy((2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H]O[C@@]([H])(C([H])([H])OP(=O)(O[H])O[H])C([H])([H])OP(=O)(O[H])OC([H])([H])[C@]([H])(OC(=O)C([H])([H])C([H])([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]
InChI Identifier
InChI=1S/C44H80O13P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-44(47)57-42(40-56-59(51,52)55-38-41(45)37-54-58(48,49)50)39-53-43(46)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h17-19,21-22,24,28,30,41-42,45H,3-16,20,23,25-27,29,31-40H2,1-2H3,(H,51,52)(H2,48,49,50)/b19-17-,21-18-,24-22-,30-28-/t41-,42+/m0/s1
InChI KeyVBHLKIRCEHLSMA-BQYWGNFBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerophosphates
Direct ParentPhosphatidylglycerophosphates
Alternative Parents
Substituents
  • Diacylglycerophosphoglycerophosphate
  • Sn-glycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • 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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.71ALOGPS
logP12.03ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.35ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area195.35 ŲChemAxon
Rotatable Bond Count44ChemAxon
Refractivity238.25 m³·mol⁻¹ChemAxon
Polarizability99.46 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-07mr-1291041350-f797aa1b5b6f78bdce95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avs-2292021310-01bc5edb18abd051b638View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7394103400-b72ab2780b4f5d2f541aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01u0-3091020120-ee3a8460f3e4d0e5994eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-096e6fef6aba072685f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-e8b35ac9443a5a694752View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000090-6d31fab7703f69222534View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9071021160-5690de2b0c7ffc576900View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ke9-8091000000-245f663c91471239de60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1010009670-9eb9f4c3f4887fe198f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-1300004900-6251ddb32a95e600f6c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0200930000-32b7deefeb61aff4fa3eView 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 IDHMDB0013540
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029540
KNApSAcK IDNot Available
Chemspider ID35032717
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481858
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available