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Showing Compound PGP(18:3(6Z,9Z,12Z)/18:0) (FDB029564)

Record Information
Version1.0
Creation date2011-09-21 01:57:41 UTC
Update date2016-06-28 20:13:42 UTC
Primary IDFDB029564
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePGP(18:3(6Z,9Z,12Z)/18:0)
DescriptionPGP(18:3(6Z,9Z,12Z)/18:0) 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)/18:0), in particular, consists of one 6Z,9Z,12Z-octadecatrienoyl chain to the C-1 atom, and one octadecanoyl 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.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
PGP(18:3(6Z,9Z,12Z)/18:0)Lipid Annotator
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acidLipid Annotator, HMDB
PGP(36:3)Lipid Annotator, HMDB
1-g-linolenoyl-2-stearoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
1-(6Z,9Z,12Z-octadecatrienoyl)-2-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
PGP(18:3/18:0)Lipid Annotator, HMDB
1-gamma-Linolenoyl-2-stearoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)HMDB
PGP(18:3n6/18:0)HMDB
PGP(18:3W6/18:0)HMDB
[(2S)-2-Hydroxy-3-({hydroxy[(2R)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-2-(octadecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonateGenerator
1-g-Linolenoyl-2-stearoyl-sn-glycero-3-O-(1'-sn-glycerol-3'-ate)HMDB
1-gamma-Linolenoyl-2-stearoyl-sn-glycero-3-O-(1'-sn-glycerol-3'-ate)HMDB
1-gamma-linolenoyl-2-stearoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)hmdb
PGP(18:3w6/18:0)hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00064 g/LALOGPS
logP7.43ALOGPS
logP11.51ChemAxon
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 Count43ChemAxon
Refractivity227.94 m³·mol⁻¹ChemAxon
Polarizability95.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC42H78O13P2
IUPAC name[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-2-(octadecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphonic acid
InChI IdentifierInChI=1S/C42H78O13P2/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/h11,13,17,19,23,25,39-40,43H,3-10,12,14-16,18,20-22,24,26-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b13-11-,19-17-,25-23-/t39-,40+/m0/s1
InChI KeyBUTGJPALEJEZBL-VLJMGXKQSA-N
Isomeric SMILESCCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)COP(=O)(O)OC[C@@]([H])(O)COP(=O)(O)O
Average Molecular Weight853.0084
Monoisotopic Molecular Weight852.491765606
Classification
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
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

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Process

Naturally occurring process:

Role

Industrial application:

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Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ldr-1290062150-45457accc616ed6cf2102017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2292022110-96c41ab3789558bca7312017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9485133300-8e263f10b4a11beea7f62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3090020020-9b067dab4ffdfd21b8db2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-add0af5aeb5e5f1c27572017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-66115fd2c27315098ce32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3112009880-35327b13987a0bac56be2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1401009800-d1248054642c87508cbc2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-0431900000-06505615cf451e02f53c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-7c6ca3412dafd58f3fd02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugj-9080171050-e9cdfb16f7a1a231a09b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-7093110000-f56b42274ccd37678abd2021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481882
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13564
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference