Showing metabocard for PGP(18:3(6Z,9Z,12Z)/18:1(9Z)) (BMDB0096789)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-03-25 16:12:55 UTC
Update Date2020-05-11 19:22:38 UTC
BMDB IDBMDB0096789
Secondary Accession NumbersNone
Metabolite Identification
Common NamePGP(18:3(6Z,9Z,12Z)/18:1(9Z))
DescriptionPGP(18:3(6Z,9Z,12Z)/18:1(9Z)) 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(18:3(6Z,9Z,12Z)/18:1(9Z)), in particular, consists of one 6Z,9Z,12Z-octadecatrienoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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(36:4)Lipid Annotator, HMDB
PGP(18:3/18:1)Lipid Annotator, HMDB
1-g-linolenoyl-2-oleoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
PGP(18:3(6Z,9Z,12Z)/18:1(9Z))Lipid Annotator
1-(6Z,9Z,12Z-octadecatrienoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acidLipid Annotator, HMDB
1-gamma-Linolenoyl-2-oleoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)HMDB
PGP(18:3n6/18:1n9)HMDB
PGP(18:3W6/18:1W9)HMDB
[(2S)-2-Hydroxy-3-({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonateGenerator
Chemical FormulaC42H76O13P2
Average Molecular Weight850.9926
Monoisotopic Molecular Weight850.476115542
IUPAC Name[(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid
Traditional Name(2S)-2-hydroxy-3-{[hydroxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C42H76O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11,13,17-20,23,25,39-40,43H,3-10,12,14-16,21-22,24,26-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b13-11-,19-17-,20-18-,25-23-/t39-,40+/m0/s1
InChI KeyXHARDXZVLWWSRI-QLADQEJGSA-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
logP7.29ALOGPS
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
Polarizability94.35 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, Positivesplash10-0gc0-1371091260-b51d38b198925ee7cc9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3493042110-41426528f06d1eb84f33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9466141300-9ebe0176ade47cb71cb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3090020010-6cc5d174ca2e38f989d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-7d58f66193e352953c2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-f8a5a41b16e905d7e533View 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, Negativesplash10-0002-9070171060-e1462356faac00d812d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-6092110000-59889d9eb195b3c30755View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-3112090880-c75488e171412ca77fd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k92-2501035900-f8c28f0ce1ff4cdac879View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ri-0330911000-3a2b734b148095e53f0aView 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 IDHMDB0013566
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029566
KNApSAcK IDNot Available
Chemspider ID35032743
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481884
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available