Showing metabocard for PGP(18:3(9Z,12Z,15Z)/16:1(9Z)) (BMDB0096799)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-03-25 16:13:44 UTC
Update Date2020-05-11 19:22:46 UTC
BMDB IDBMDB0096799
Secondary Accession NumbersNone
Metabolite Identification
Common NamePGP(18:3(9Z,12Z,15Z)/16:1(9Z))
DescriptionPGP(18:3(9Z,12Z,15Z)/16:1(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(9Z,12Z,15Z)/16:1(9Z)), in particular, consists of one 9Z,12Z,15Z-octadecatrienoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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(18:3/16:1)Lipid Annotator, HMDB
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acidLipid Annotator, HMDB
PGP(34:4)Lipid Annotator, HMDB
PGP(18:3(9Z,12Z,15Z)/16:1(9Z))Lipid Annotator
1-(9Z,12Z,15Z-octadeatrienoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
1-a-linolenoyl-2-palmitoleoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
1-alpha-Linolenoyl-2-palmitoleoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)HMDB
PGP(18:3n3/16:1n7)HMDB
PGP(18:3W3/16:1W7)HMDB
[(2S)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonateGenerator
Chemical FormulaC40H72O13P2
Average Molecular Weight822.9394
Monoisotopic Molecular Weight822.444815414
IUPAC Name[(2S)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional Name(2S)-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-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)CCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C40H72O13P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(42)49-35-38(36-52-55(47,48)51-34-37(41)33-50-54(44,45)46)53-40(43)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h5,7,11,13-14,16-18,37-38,41H,3-4,6,8-10,12,15,19-36H2,1-2H3,(H,47,48)(H2,44,45,46)/b7-5-,13-11-,16-14-,18-17-/t37-,38+/m0/s1
InChI KeyLCYRMJJWUBDAOB-NJXCWUJZSA-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
logP6.77ALOGPS
logP10.25ChemAxon
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 Count40ChemAxon
Refractivity219.85 m³·mol⁻¹ChemAxon
Polarizability89.58 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, Positivesplash10-0abi-1390061140-7e910fde1db840101511View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cds-2391021110-b8710900e7dea5acc7b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7594131200-11d8725dac5e3a24eaafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3090020010-3f21f8a815f7b5f90b7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-7535956189f0d07bb8dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-9709f09b7d655c4ef265View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-b50a4bdc787dab205799View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ba-9070161060-100d2740947bd130ad2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-8092120000-66438ed20636579d137dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3011091880-f839a9e6895e4b8e3dceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00vi-2300039600-8ce998069968cb72d5e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-1554913000-712738aab662e68ca44fView 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 IDHMDB0013578
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029578
KNApSAcK IDNot Available
Chemspider ID35032755
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481896
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available