Showing metabocard for PGP(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (BMDB0096811)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-03-25 16:14:43 UTC
Update Date2020-05-11 19:22:56 UTC
BMDB IDBMDB0096811
Secondary Accession NumbersNone
Metabolite Identification
Common NamePGP(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPGP(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one 9Z,12Z,15Z-octadecatrienoyl chain to the C-1 atom, and one 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl 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(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acidLipid Annotator, HMDB
1-a-linolenoyl-2-docosahexaenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
PGP(18:3/22:6)Lipid Annotator, HMDB
1-(9Z,12Z,15Z-octadeatrienoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
PGP(40:9)Lipid Annotator, HMDB
1-alpha-Linolenoyl-2-docosahexaenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)HMDB
PGP(18:3n3/22:6n3)HMDB
PGP(18:3W3/22:6W3)HMDB
[(2S)-3-({[(2R)-2-[(4Z,7Z,10Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonateGenerator
Chemical FormulaC46H74O13P2
Average Molecular Weight897.0195
Monoisotopic Molecular Weight896.460465478
IUPAC Name[(2S)-3-({[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional Name(2S)-3-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-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/C\C=C/C\C=C/CC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C46H74O13P2/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-46(49)59-44(42-58-61(53,54)57-40-43(47)39-56-60(50,51)52)41-55-45(48)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-19,21-23,26,28,32,34,43-44,47H,3-4,9-10,15-16,20,24-25,27,29-31,33,35-42H2,1-2H3,(H,53,54)(H2,50,51,52)/b7-5-,8-6-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,34-32-/t43-,44+/m0/s1
InChI KeyCIVIANHBKXRQIE-JRJQDFDNSA-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
logP7.18ALOGPS
logP11.11ChemAxon
logS-5.9ALOGPS
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 Count41ChemAxon
Refractivity253.04 m³·mol⁻¹ChemAxon
Polarizability96.24 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, Positivesplash10-0401-1396045470-465ebb32311ba78bb8c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-3395023310-8d0894967ff5acee26fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9377104500-89368b6cce5d9c5b12fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4092020120-7a2133b299f83c94cd2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-5f26247d72a3e2f3e9feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8136d7c6e32b74a20c00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-dc822b97ae45c1dceaeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-9051014160-f58ec12402016c52b8f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-6092000010-1c7e4b9530dd7fa5a4b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2100008790-d2d053df7e560ec8e74dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-2100002900-13ce5dc4a526279b1a35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2431961600-325fc321c2f72970d495View 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 IDHMDB0013591
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029591
KNApSAcK IDNot Available
Chemspider ID35032768
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481909
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available