Showing metabocard for PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) (BMDB0096736)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-03-25 16:08:24 UTC
Update Date2020-05-11 19:21:54 UTC
BMDB IDBMDB0096736
Secondary Accession NumbersNone
Metabolite Identification
Common NamePGP(16:1(9Z)/20:3(5Z,8Z,11Z))
DescriptionPGP(16:1(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(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, 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(16:1(9Z)/20:3(5Z,8Z,11Z))Lipid Annotator
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acidLipid Annotator, HMDB
PGP(16:1/20:3)Lipid Annotator, HMDB
1-palmitoleoyl-2-meadoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
1-(9Z-hexadecenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
PGP(36:4)Lipid Annotator, HMDB
PGP(16:1n7/20:3n9)HMDB
PGP(16:1W7/20:3W9)HMDB
Chemical FormulaC42H76O13P2
Average Molecular Weight850.9926
Monoisotopic Molecular Weight850.476115542
IUPAC Name[(2S)-3-({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional Name(2S)-3-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(COP(O)(O)=O)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/C42H76O13P2/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-42(45)55-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)37-51-41(44)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h14,16-18,20,22,26,28,39-40,43H,3-13,15,19,21,23-25,27,29-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b16-14-,18-17-,22-20-,28-26-/t39-,40+/m0/s1
InChI KeyJZUYPUNJRHZLJE-OILVUHFKSA-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
logP7.33ALOGPS
logP11.14ChemAxon
logS-6.1ALOGPS
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 Count42ChemAxon
Refractivity229.05 m³·mol⁻¹ChemAxon
Polarizability94.88 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, Positivesplash10-0k9j-1290060140-a15bbe1cb9c86da1fe02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-2391031110-895e8adfe7577047bcb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-6391021200-d533c8e181b48cc191beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kbs-3091021020-74356f9e346dc4a428fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-49145be7a0d48152a441View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4b2977d777bea260ca57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-40abed2e3880a3dd0c54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9041171060-abfbcbc89bafa285981bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kdi-8096120000-d5e4d5423df361be75a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-3110090680-588e353cf7faf1c7a0e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k92-3410046900-a81def28f8590a24bebaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p7-1101934100-a426d4ddec31a0b88f20View 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 IDHMDB0013495
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029495
KNApSAcK IDNot Available
Chemspider ID35032673
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481814
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available