Showing metabocard for PG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (BMDB0010687)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:11:49 UTC
Update Date2020-05-11 19:13:35 UTC
BMDB IDBMDB0010687
Secondary Accession Numbers
  • BMDB10687
Metabolite Identification
Common NamePG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))
DescriptionPG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)) 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(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one 9Z,12Z,15Z-octadecatrienoyl chain to the C-1 atom, and one 4Z,7Z,10Z,13Z,16Z-docosapentaenoyl 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
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phospho-(1'-glycerol)HMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phospho-(1'-glycerol)HMDB
1-a-Linolenoyl-2-docosapentaenoyl-sn-glycero-3-phosphoglycerolHMDB
1-a-Linolenoyl-2-osbondoyl-sn-glycero-3-phosphoglycerolHMDB
1-alpha-Linolenoyl-2-docosapentaenoyl-sn-glycero-3-phosphoglycerolHMDB
1-alpha-Linolenoyl-2-osbondoyl-sn-glycero-3-phosphoglycerolHMDB
GPG(18:3/22:5)HMDB
GPG(18:3N3/22:5N6)HMDB
GPG(18:3W3/22:5W6)HMDB
GPG(40:8)HMDB
PG(18:3/22:5)HMDB
PG(18:3N3/22:5N6)HMDB
PG(18:3W3/22:5W6)HMDB
PG(40:8)HMDB
Phosphatidylglycerol(18:3/22:5)HMDB
Phosphatidylglycerol(18:3n3/22:5n6)HMDB
Phosphatidylglycerol(18:3W3/22:5W6)HMDB
Phosphatidylglycerol(40:8)HMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphoglycerolHMDB
[(2S)-2,3-Dihydroxypropoxy][(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphinateHMDB
PG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))Lipid Annotator
Chemical FormulaC46H75O10P
Average Molecular Weight819.0555
Monoisotopic Molecular Weight818.509785132
IUPAC Name[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphinic acid
Traditional Name(2S)-2,3-dihydroxypropoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)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/CCCCC
InChI Identifier
InChI=1S/C46H75O10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-46(50)56-44(42-55-57(51,52)54-40-43(48)39-47)41-53-45(49)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-19,21-23,26,28,32,34,43-44,47-48H,3-5,7,9-10,15-16,20,24-25,27,29-31,33,35-42H2,1-2H3,(H,51,52)/b8-6-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,34-32-/t43-,44+/m0/s1
InChI KeyVIOWOHCJGLIEBH-TVFHYZSLSA-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
logP7.72ALOGPS
logP11.6ChemAxon
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
Refractivity241.05 m³·mol⁻¹ChemAxon
Polarizability93.64 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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0j4i-4186432190-f32eedc425748ac13636View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0imi-6195221220-0d3edf595f81188df3a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9087003200-cf5a1cb1130433e6ce30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-1193110220-834cd52ee25b2ec0fc8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5291100100-e6a716ea954e4da1f875View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9011000000-712a4b3dc871b5569106View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-0b4d0111725d5ac858ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-0199440090-b097ac47f5e87d33fb6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0399440090-007259d0ef34f766a156View 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 IDHMDB0010687
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027837
KNApSAcK IDNot Available
Chemspider ID24768186
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480643
PDB IDNot Available
ChEBI ID89318
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available