Showing metabocard for PG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)) (BMDB0010596)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:09:59 UTC
Update Date2020-05-11 19:12:20 UTC
BMDB IDBMDB0010596
Secondary Accession Numbers
  • BMDB10596
Metabolite Identification
Common NamePG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))
DescriptionPG(16:1(9Z)/22:4(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(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one 7Z,10Z,13Z,16Z-docosatetraenoyl 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
PG(38:5)Lipid Annotator, HMDB
GPG(38:5)Lipid Annotator, HMDB
1-(9Z-hexadecenoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phospho-(1'-glycerol)Lipid Annotator, HMDB
Phosphatidylglycerol(16:1/22:4)Lipid Annotator, HMDB
1-palmitoleoyl-2-adrenoyl-sn-glycero-3-phosphoglycerolLipid Annotator, HMDB
PG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))Lipid Annotator
PG(16:1/22:4)Lipid Annotator, HMDB
GPG(16:1/22:4)Lipid Annotator, HMDB
1-(9Z-hexadecenoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphoglycerolLipid Annotator, HMDB
Phosphatidylglycerol(38:5)Lipid Annotator, HMDB
GPG(16:1N7/22:4N6)HMDB
GPG(16:1W7/22:4W6)HMDB
PG(16:1N7/22:4N6)HMDB
PG(16:1W7/22:4W6)HMDB
Phosphatidylglycerol(16:1n7/22:4n6)HMDB
Phosphatidylglycerol(16:1W7/22:4W6)HMDB
Chemical FormulaC44H77O10P
Average Molecular Weight797.0499
Monoisotopic Molecular Weight796.525435196
IUPAC Name[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid
Traditional Name(2S)-2,3-dihydroxypropoxy(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C44H77O10P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-44(48)54-42(40-53-55(49,50)52-38-41(46)37-45)39-51-43(47)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h11,13-14,16-18,20-21,24,26,41-42,45-46H,3-10,12,15,19,22-23,25,27-40H2,1-2H3,(H,49,50)/b13-11-,16-14-,18-17-,21-20-,26-24-/t41-,42+/m0/s1
InChI KeyLVQOWSPRPQUBPY-MCQYTGMZSA-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 Descriptors
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
logP8.17ALOGPS
logP11.79ChemAxon
logS-7ALOGPS
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 Count41ChemAxon
Refractivity228.5 m³·mol⁻¹ChemAxon
Polarizability93.34 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, Positivesplash10-00or-4175522900-4cb66d6db2d49ac3e0eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r0-6294211400-0eaa1e2a6a1d194d2ddcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-8194203200-0e74de31ef958d2aa513View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uei-1193200400-172a4b80069e5f97b624View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-5291100100-2f7e1f882658ee1fefa3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9011000000-a2878c2e0870c24f77dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-9869f21529424c0a4adfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uf1-0179320700-b62e89afd6810140a1c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uf1-0279320700-e9bc3e6deaeb6a222638View 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 IDHMDB0010596
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027746
KNApSAcK IDNot Available
Chemspider ID24768095
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52926490
PDB IDNot Available
ChEBI ID89074
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available