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PG(19:0cycv8c/18:1(9Z)) (M2MDB006520)

Record Information
Version2.0
Creation Date2015-09-08 19:31:01 -0600
Update Date2015-12-09 12:08:35 -0700
Secondary Accession Numbers
  • ECMDB24403
Identification
Name:PG(19:0cycv8c/18:1(9Z))
DescriptionPG(19:0cycv8c/18:1(9Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(19:0cycv8c/18:1(9Z)), in particular, consists of one heptadec-11-12-cyclo-anoyl chain to the C-1 atom, and one 9Z-octadecenoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:Not Available
Chemical Formula:C43H81O10P
Weight:Average: 789.085
Monoisotopic: 788.556735806
InChI Key:OWUSTQQQYYIYQD-SURQDNLTSA-N
InChI:InChI=1S/C43H81O10P/c1-3-5-7-9-10-11-12-13-14-15-16-17-20-23-27-31-42(46)50-36-41(37-52-54(48,49)51-35-40(45)34-44)53-43(47)32-28-24-21-18-19-22-26-30-39-33-38(39)29-25-8-6-4-2/h13-14,38-41,44-45H,3-12,15-37H2,1-2H3,(H,48,49)/b14-13-/t38?,39?,40-,41+/m0/s1
CAS number:Not Available
IUPAC Name:[(2S)-2,3-dihydroxypropoxy][(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name:(2S)-2,3-dihydroxypropoxy((2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid
SMILES:[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols 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 ClassGlycerophosphoglycerols
Direct ParentPhosphatidylglycerols
Alternative Parents
Substituents
  • 1,2-diacylglycerophosphoglycerol
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.4e-05 g/LALOGPS
logP8.42ALOGPS
logP12.02ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area148.82 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity217.52 m³·mol⁻¹ChemAxon
Polarizability95.55 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
PGP(19:0cycv8c/18:1(9Z)) + Water > PG(19:0cycv8c/18:1(9Z)) + Phosphate
PE(17:0cycw7c/17:0cycw7c) + PG(19:0cycv8c/18:1(9Z)) > Ethanolamine + CL(19:0cycv8c/18:1(9Z)/17:0cycw7c/17:0cycw7c)
PE(14:0/18:1(9Z)) + PG(19:0cycv8c/18:1(9Z)) > Ethanolamine + CL(19:0cycv8c/18:1(9Z)/14:0/18:1(9Z))
SMPDB Pathways:
phospholipid biosynthesis (CL(19:0cycv8c/18:1(9Z)/14:0/18:1(9Z)))PW001415 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/18:1(9Z)/17:0cycw7c/17:0cycw7c))PW001422 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, Positivesplash10-00vr-3091321700-27fe85b7785e1be865e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r0-4191214300-c735bc70527aae0a35e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar9-9065304200-8621d9a5f9ee24a8e432View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01qj-0190110300-08122925a0b3a1f0ff98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-4290100100-9c8b1dcdd972b2b9faa3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020000000-40da9c4abc6beee8f5c5View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
  • 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.
Protein Details
3. Cardiolipin synthase C
General function:
cardiolipin biosynthetic process
Specific function:
Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) from phosphatidylglycerol (PG) and phosphatidylethanolamine (PE).
Gene Name:
clsC
Uniprot ID:
P75919
Molecular weight:
53665
Reactions
Phosphatidylglycerol + phosphatidylethanolamine = diphosphatidylglycerol + ethanolamine