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Showing Compound PGP(18:3(6Z,9Z,12Z)/18:1(11Z)) (FDB029565)

Record Information
Version1.0
Creation date2011-09-21 01:57:41 UTC
Update date2015-07-21 06:59:46 UTC
Primary IDFDB029565
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePGP(18:3(6Z,9Z,12Z)/18:1(11Z))
DescriptionPGP(18:3(6Z,9Z,12Z)/18:1(11Z)) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PGP(18:3(6Z,9Z,12Z)/18:1(11Z)), in particular, consists of one chain of g-linolenic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The g-linolenic acid moiety is derived from animal fats, while the vaccenic acid moiety is derived from butter fat and animal fat. Phosphatidylglycerolphosphate is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of Phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGPs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
PGP(36:4)Lipid Annotator, HMDB
PGP(18:3/18:1)Lipid Annotator, HMDB
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acidLipid Annotator, HMDB
1-g-linolenoyl-2-vaccenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
1-(6Z,9Z,12Z-octadecatrienoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)Lipid Annotator, HMDB
PGP(18:3(6Z,9Z,12Z)/18:1(11Z))Lipid Annotator
1-gamma-Linolenoyl-2-vaccenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)HMDB
PGP(18:3n6/18:1n7)HMDB
PGP(18:3W6/18:1W7)HMDB
[(2S)-2-Hydroxy-3-({hydroxy[(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonateGenerator
1-g-Linolenoyl-2-vaccenoyl-sn-glycero-3-O-(1'-sn-glycerol-3'-ate)HMDB
1-gamma-Linolenoyl-2-vaccenoyl-sn-glycero-3-O-(1'-sn-glycerol-3'-ate)HMDB
1-gamma-linolenoyl-2-vaccenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)hmdb
PGP(18:3w6/18:1w7)hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00074 g/LALOGPS
logP7.29ALOGPS
logP11.14ChemAxon
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 Count42ChemAxon
Refractivity229.05 m³·mol⁻¹ChemAxon
Polarizability93.95 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC42H76O13P2
IUPAC name[(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid
InChI IdentifierInChI=1S/C42H76O13P2/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/h11,13-14,16-17,19,23,25,39-40,43H,3-10,12,15,18,20-22,24,26-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b13-11-,16-14-,19-17-,25-23-/t39-,40+/m0/s1
InChI KeyGZARRVRNAQQTBA-PCIHCSGPSA-N
Isomeric SMILESCCCCCC\C=C/CCCCCCCCCC(=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 Weight850.9926
Monoisotopic Molecular Weight850.476115542
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:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
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, Positivesplash10-0gc0-1371091260-b5a0a365308adeeabeaf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3493042110-1078574348d8fb36bb0a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9466141300-8b9db4fb479e3f3a332a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3090020010-6cc5d174ca2e38f989d32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-7d58f66193e352953c2a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-f8a5a41b16e905d7e5332017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-3012090880-d4e6b155ffa44cff69f62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k92-1401036900-6b3f8c6aeb430b0d33f62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1340920100-a5971a87c7a7701c4d282021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000090-40abed2e3880a3dd0c542021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9070171060-e1462356faac00d812d02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-6092110000-59889d9eb195b3c307552021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481883
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13565
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