Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


Record Information
Version2.0
Creation Date2015-09-08 19:35:15 -0600
Update Date2015-12-09 17:20:28 -0700
Secondary Accession Numbers
  • ECMDB24492
Identification
Name:PGP(16:1(9Z)/14:0(3-OH))
DescriptionPGP(16:1(9Z)/14:0(3-OH)) 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(16:1(9Z)/14:0(3-OH)), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one 3-hydroxytetradecanoyl 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
Synonyms:Not Available
Chemical Formula:C36H70O14P2
Weight:Average: 788.89
Monoisotopic: 788.42408093
InChI Key:QULLFIPZTDKOPB-FNFUOXECSA-N
InChI:InChI=1S/C36H70O14P2/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-35(39)46-30-34(31-49-52(44,45)48-29-33(38)28-47-51(41,42)43)50-36(40)27-32(37)25-23-21-19-17-12-10-8-6-4-2/h13-14,32-34,37-38H,3-12,15-31H2,1-2H3,(H,44,45)(H2,41,42,43)/b14-13-/t32?,33-,34-/m1/s1
CAS number:Not Available
IUPAC Name:[(2R)-3-({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(3-hydroxytetradecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:(2R)-3-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(3-hydroxytetradecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CC(O)CCCCCCCCCCC
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
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0032 g/LALOGPS
logP5.31ALOGPS
logP8.33ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)1.35ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area215.58 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity199.61 m³·mol⁻¹ChemAxon
Polarizability87.3 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
phospholipid biosynthesis (CL(16:1(9Z)/14:0(3-OH)/16:1(9Z)/14:0(3-OH)))PW001958 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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, Positivesplash10-0079-1490062700-4cdaaa49e0a4ea2a1434View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a71-3590041200-b1c37a4f6f90ce5b0c42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9862134000-2a5b108842b51a5b7918View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f9i-3090021200-cc610d1678b20abfba5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9060000000-b5c19e46048a8b38debdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-2fb1fe39c75669d8648cView in MoNA
References
References:
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Hydrolyzes phosphatidylglycerophosphate, phosphatidic acid, and lysophosphatidic acid; the pattern of activities varies according to subcellular location
Gene Name:
pgpB
Uniprot ID:
P0A924
Molecular weight:
29021
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
This protein catalyzes the committed step to the synthesis of the acidic phospholipids
Gene Name:
pgsA
Uniprot ID:
P0ABF8
Molecular weight:
20700
Reactions
CDP-diacylglycerol + sn-glycerol 3-phosphate = CMP + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphate.
General function:
Involved in phosphatidylglycerophosphatase activity
Specific function:
One of the three phospholipid phosphatases, specifically hydrolyzes phosphatidylglycerophosphate
Gene Name:
pgpA
Uniprot ID:
P18200
Molecular weight:
19418
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.