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PGP(10:0(3-OH)/17:0cycw7c) (M2MDB006538)

Record Information
Version2.0
Creation Date2015-09-08 19:31:47 -0600
Update Date2015-12-09 17:18:06 -0700
Secondary Accession Numbers
  • ECMDB24421
Identification
Name:PGP(10:0(3-OH)/17:0cycw7c)
DescriptionPGP(10:0(3-OH)/17:0cycw7c) 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(10:0(3-OH)/17:0cycw7c), in particular, consists of one 3-hydroxydecanoyl chain to the C-1 atom, and one heptadec-9-10-cyclo-anoyl 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:C33H64O14P2
Weight:Average: 746.809
Monoisotopic: 746.377130737
InChI Key:OWVRLQFVTUVOAO-FOMSTSDASA-N
InChI:InChI=1S/C33H64O14P2/c1-3-5-7-10-15-19-29(34)22-33(37)43-25-31(26-46-49(41,42)45-24-30(35)23-44-48(38,39)40)47-32(36)20-16-12-9-11-14-18-28-21-27(28)17-13-8-6-4-2/h27-31,34-35H,3-26H2,1-2H3,(H,41,42)(H2,38,39,40)/t27?,28?,29?,30-,31-/m1/s1
CAS number:Not Available
IUPAC Name:[(2R)-3-({[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:(2R)-3-{[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCC)OC(=O)CCCCCCCC1CC1CCCCCC
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 homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0036 g/LALOGPS
logP4.22ALOGPS
logP6.58ChemAxon
logS-5.3ALOGPS
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 Count35ChemAxon
Refractivity182.79 m³·mol⁻¹ChemAxon
Polarizability81.12 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
2 CDP-DG(10:0(3-OH)/17:0cycw7c) + Glycerol 3-phosphate >2 PGP(10:0(3-OH)/17:0cycw7c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 PGP(10:0(3-OH)/17:0cycw7c) + Water >2 PG(10:0(3-OH)/17:0cycw7c) + Phosphate
SMPDB Pathways:
phospholipid biosynthesis (CL(10:0(3-OH)/17:0cycw7c/10:0(3-OH)/17:0cycw7c))PW001906 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(10:0(3-OH)/17:0cycw7c/14:0/14:0))PW001907 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_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1870622900-d4c7f4b2e00d103ba587View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pdj-4971321300-bc5ec900e55de82120f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9761402000-dc8ae74056fc0f9b776fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016s-5950210300-57397fc7b53d76b7e128View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9320000000-6d8044d201d8bf8639e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-77567b9f7803d7c257abView in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
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. CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase
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.
Protein Details
3. 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.