PGP(18:1(9Z)/14:0(3-OH)) (ECMDB24509) (M2MDB006626)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 19:36:14 -0600
Update Date2015-12-09 17:21:14 -0700
Secondary Accession Numbers
  • ECMDB24509
Identification
Name:PGP(18:1(9Z)/14:0(3-OH))
DescriptionPGP(18:1(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(18:1(9Z)/14:0(3-OH)), in particular, consists of one 9Z-octadecenoyl 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
MOLSDFPDBSMILESInChI
Synonyms:Not Available
Chemical Formula:C38H74O14P2
Weight:Average: 816.944
Monoisotopic: 816.455381059
InChI Key:SVSNEKXENYDOOP-AIFQWCCOSA-N
InChI:InChI=1S/C38H74O14P2/c1-3-5-7-9-11-13-14-15-16-17-18-20-22-24-26-28-37(41)48-32-36(33-51-54(46,47)50-31-35(40)30-49-53(43,44)45)52-38(42)29-34(39)27-25-23-21-19-12-10-8-6-4-2/h15-16,34-36,39-40H,3-14,17-33H2,1-2H3,(H,46,47)(H2,43,44,45)/b16-15-/t34?,35-,36-/m1/s1
CAS number:Not Available
IUPAC Name:[(2R)-2-hydroxy-3-({hydroxy[(2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid
Traditional IUPAC Name:(2R)-2-hydroxy-3-{[hydroxy((2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid
SMILES:[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)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 Solubility0.002 g/LALOGPS
logP5.86ALOGPS
logP9.22ChemAxon
logS-5.6ALOGPS
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 Count41ChemAxon
Refractivity208.81 m³·mol⁻¹ChemAxon
Polarizability91.95 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
2 PGP(18:1(9Z)/14:0(3-OH)) + Water >2 PG(18:1(9Z)/14:0(3-OH)) + Phosphate
SMPDB Pathways:
phospholipid biosynthesis (CL(18:1(9Z)/19:0cycv8c/18:1(9Z)/14:0))PW001244 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_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066s-1390060720-97f93c353229a03c9f4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar1-2491040300-0c4541ca2ec31bf43fdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9763132200-8fd0682714566f6d2a36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01u1-3090020110-6ecf35c21ef90ea55a77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9060000000-c82f312db15926dbb2baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-0c77a938829f5dac9cc9View 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

Protein Details
1. Phosphatidylglycerophosphatase B
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.
Protein Details
2. Phosphatidylglycerophosphatase A
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.