PGP(12:0(3-OH)/12:0) (ECMDB24432) (M2MDB006549)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 19:32:18 -0600
Update Date2015-12-09 17:18:21 -0700
Secondary Accession Numbers
  • ECMDB24432
Identification
Name:PGP(12:0(3-OH)/12:0)
DescriptionPGP(12:0(3-OH)/12:0) 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(12:0(3-OH)/12:0), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one dodecanoyl 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:C30H60O14P2
Weight:Average: 706.744
Monoisotopic: 706.345830608
InChI Key:WBKNAIBDNFYZTA-DXISBFFWSA-N
InChI:InChI=1S/C30H60O14P2/c1-3-5-7-9-11-12-14-16-18-20-29(33)44-28(25-43-46(38,39)42-23-27(32)22-41-45(35,36)37)24-40-30(34)21-26(31)19-17-15-13-10-8-6-4-2/h26-28,31-32H,3-25H2,1-2H3,(H,38,39)(H2,35,36,37)/t26?,27-,28-/m1/s1
CAS number:Not Available
IUPAC Name:[(2R)-3-({[(2R)-2-(dodecanoyloxy)-3-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:(2R)-3-{[(2R)-2-(dodecanoyloxy)-3-[(3-hydroxydodecanoyl)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)CCCCCCCCC)OC(=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 Solubility0.017 g/LALOGPS
logP3.53ALOGPS
logP6.03ChemAxon
logS-4.6ALOGPS
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 Count34ChemAxon
Refractivity170.89 m³·mol⁻¹ChemAxon
Polarizability76.78 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
2 PGP(12:0(3-OH)/12:0) + Water >2 PG(12:0(3-OH)/12:0) + Phosphate
SMPDB Pathways:
phospholipid biosynthesis (CL(12:0(3-OH)/12:0(3-OH)/12:0/12:0))PW001915 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, Positivesplash10-0a5i-1920435100-24507ce33b307fc5fb7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5a-2910221000-0a58a6f20ce9a23d3361View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5930311000-23a3f5083eb6249a43acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-4930041200-87fe47178e0af33e94a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9320000000-8aa7a2974316a77ac59eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-41af10ed385248e8dbdfView 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.