Record Information
Version2.0
Creation Date2012-05-31 14:54:23 -0600
Update Date2015-12-09 12:06:57 -0700
Secondary Accession Numbers
  • ECMDB21013
Identification
Name:PG(14:0/14:0)
Description:PG(14:0/14:0) 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(14:0/14:0), in particular, consists of two tetradecanoyl chains at positions C-1 and C-2. 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
Synonyms:
  • 1,2-dimyristoyl-rac-glycero-3-phosphoglycerol
  • 1,2-ditetradecanoyl-rac-glycero-3-phospho-(1'-glycerol)
  • 1,2-ditetradecanoyl-rac-glycero-3-phosphoglycerol
  • GPG(14:0/14:0)
  • GPG(28:0)
  • GPGro(14:0/14:0)
  • PG(28:0)
  • Phosphatidylglycerol(14:0/14:0)
  • Phosphatidylglycerol(28:0)
Chemical Formula:C34H67O10P
Weight:Average: 666.874
Monoisotopic: 666.447185355
InChI Key:BPHQZTVXXXJVHI-AJQTZOPKSA-N
InChI:InChI=1S/C34H67O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-33(37)41-29-32(30-43-45(39,40)42-28-31(36)27-35)44-34(38)26-24-22-20-18-16-14-12-10-8-6-4-2/h31-32,35-36H,3-30H2,1-2H3,(H,39,40)/t31-,32+/m0/s1
CAS number:Not Available
IUPAC Name:[(2R)-2,3-bis(tetradecanoyloxy)propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional IUPAC Name:(2R)-2,3-bis(tetradecanoyloxy)propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
SMILES:[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC
Chemical Taxonomy
DescriptionThis compound 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 acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00028 g/LALOGPS
logP6.79ALOGPS
logP9.16ChemAxon
logS-6.4ALOGPS
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 Count36ChemAxon
Refractivity176.9 m³·mol⁻¹ChemAxon
Polarizability79 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Water + PGP(14:0/14:0) > PG(14:0/14:0) + Phosphate
2 PG(14:0/14:0) <> cardiolipin (tetratetradecanoyl, n-C14:0) + Glycerol
Water + PGP(14:0/14:0) > PG(14:0/14:0) + Phosphate
Adenosine triphosphate + Water + PG(14:0/14:0) > ADP + Hydrogen ion + Phosphate + PG(14:0/14:0)
Adenosine triphosphate + Water + PG(14:0/14:0) > ADP + Hydrogen ion + Phosphate + PG(14:0/14:0)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + Adenosine triphosphate + tetradecanoate (n-C14:0) > Adenosine monophosphate + PG(14:0/14:0) + Pyrophosphate
Water + PG(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + Hydrogen ion + tetradecanoate (n-C14:0)
Water + PG(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + Hydrogen ion + tetradecanoate (n-C14:0)
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:0) + PG(14:0/14:0) > Acyl phosphatidylglycerol (N-C14:0) + Glycerylphosphorylethanolamine
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + PG(14:0/14:0) > Acyl phosphatidylglycerol (N-C14:0) + Glycerophosphoglycerol
PGP(14:0/14:0) + Water > PG(14:0/14:0) + Phosphate
PG(14:0/14:0) + PE(15:0/17:0cycw7c) > Ethanolamine + CL(14:0/15:0cyclo/17:0cycw7c/14:0)
PE(14:0/16:0) + PG(14:0/14:0) > Ethanolamine + CL(14:0/16:0/14:0/14:0)
PE(16:0/19:0cycw8c) + PG(14:0/14:0) > Ethanolamine + CL(14:0/16:0/14:0/19:0cycv8c)
PG(14:0/14:0) + PE(16:0/19:0cycw8c) > Ethanolamine + CL(14:0/16:0/19:0cycv8c/14:0)
PE(16:1(9Z)/16:1(9Z)) + PG(14:0/14:0) > CL(14:0/16:1(9Z)/14:0/16:1(9Z)) + Ethanolamine
PE(16:1(9Z)/18:1(9Z)) + PG(14:0/14:0) > Ethanolamine + CL(14:0/16:1(9Z)/14:0/18:1(9Z))
PG(14:0/14:0) + PE(16:1(9Z)/19:iso) > Ethanolamine + CL(14:0/16:1(9Z)/14:0/19:0cycv8c)
PE(16:1(9Z)/18:1(9Z)) + PG(14:0/14:0) > Ethanolamine + CL(14:0/16:1(9Z)/18:1(9Z)/14:0)
PG(14:0/14:0) + PE(16:1(9Z)/19:iso) > Ethanolamine + CL(14:0/16:1(9Z)/19:0cycv8c/14:0)
PG(14:0/14:0) + PE(14:0/18:1(9Z)) > Ethanolamine + CL(14:0/18:1(9Z)/14:0/14:0)
PG(14:0/14:0) + PE(18:1(9Z)/18:1(9Z)) > Ethanolamine + CL(14:0/18:1(9Z)/14:0/18:1(9Z))
PG(14:0/14:0) + PE(18:1(9Z)/19:iso) > Ethanolamine + CL(14:0/18:1(9Z)/14:0/19:0cycv8c)
PG(14:0/14:0) + PE(17:0/18:1(11Z)) > Ethanolamine + CL(14:0/18:1(9Z)/17:0cycw7c/14:0)
PG(14:0/14:0) + PE(18:1(9Z)/19:iso) > Ethanolamine + CL(14:0/18:1(9Z)/19:0cycv8c/14:0)
PG(14:0/14:0) + PE(17:0cycw7c/19:iso) > Ethanolamine + CL(14:0/19:0cycv8c/14:0/17:0cycw7c)
PG(14:0/14:0) + PE(19:0cycv8c/19:iso) > Ethanolamine + CL(14:0/19:0cycv8c/14:0/19:0cycv8c)
PG(14:0/14:0) + PE(17:0cycw7c/19:iso) > CL(14:0/19:0cycv8c/17:0cycw7c/14:0) + Ethanolamine
PE(15:0cyclo/19:iso) + PG(14:0/14:0) > Ethanolamine + CL(15:0cyclo/14:0/14:0/17:0cycw7c)
PE(15:0/17:0cycw7c) + PG(14:0/14:0) > Ethanolamine + CL(15:0cyclo/17:0cycw7c/14:0/14:0)
PG(14:0/14:0) + PE(14:0/16:0) > Ethanolamine + CL(16:0/14:0/14:0/14:0)
PE(16:0/19:0cycw8c) + PG(14:0/14:0) > Ethanolamine + CL(16:0/14:0/14:0/19:0cycv8c)
PE(16:0/18:1(9Z)) + PG(14:0/14:0) > Ethanolamine + CL(16:0/14:0/18:1(9Z)/14:0)
PE(16:0/19:0cycw8c) + PG(14:0/14:0) > CL(16:0/14:0/19:0cycv8c/14:0) + Ethanolamine
PG(14:0/14:0) + PE(16:1(9Z)/16:0) > CL(16:0/16:1(9Z)/14:0/14:0) + Ethanolamine
PG(14:0/14:0) + PE(19:0/17:0) > Ethanolamine + CL(19:0cycv8c/16:0/19:0cycv8c/14:0)
PG(14:0/14:0) + PE(16:0/18:1(9Z)) > CL(16:0/18:1(9Z)/14:0/14:0) + Ethanolamine
PG(14:0/14:0) + PE(16:0/19:0cycw8c) > Ethanolamine + CL(16:0/19:0cycv8c/14:0/14:0)
PG(14:0/14:0) + PE(16:1(9Z)/16:1(9Z)) > Ethanolamine + CL(16:1(9Z)/14:0/14:0/16:1(9Z))
PG(14:0/14:0) + PE(16:1(9Z)/18:1(9Z)) > CL(16:1(9Z)/14:0/14:0/18:1(9Z)) + Ethanolamine
PE(16:1(9Z)/19:iso) + PG(14:0/14:0) > CL(16:1(9Z)/14:0/14:0/19:0cycv8c) + Ethanolamine
PG(14:0/14:0) + PE(16:1(9Z)/16:1(9Z)) > CL(16:1(9Z)/14:0/16:1(9Z)/14:0) + Ethanolamine
PG(14:0/14:0) + PE(16:1(9Z)/18:1(9Z)) > Ethanolamine + CL(16:1(9Z)/14:0/18:1(9Z)/14:0)
PG(14:0/14:0) + PE(16:1(9Z)/19:iso) > Ethanolamine + CL(16:1(9Z)/14:0/19:0cycv8c/14:0)
PG(14:0/14:0) + PE(16:0/16:1(9Z)) > Ethanolamine + CL(16:1(9Z)/16:0/14:0/14:0)
PE(19:0/16:0) + PG(14:0/14:0) > Ethanolamine + CL(17:0cycw7c/19:0cycv8c/17:0cycw7c/14:0)
PE(17:0/14:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/14:0/17:0cycw7c/14:0)
PG(14:0/14:0) + PE(16:1(9Z)/16:1(9Z)) > Ethanolamine + CL(16:1(9Z)/16:1(9Z)/14:0/14:0)
PE(19:0/16:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/16:0/18:1(9Z))
PG(14:0/14:0) + PE(16:1(9Z)/18:1(9Z)) > CL(16:1(9Z)/18:1(9Z)/14:0/14:0) + Ethanolamine
PE(19:0/17:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/16:0/18:1(9Z)/16:0)
PG(14:0/14:0) + PE(16:1(9Z)/19:iso) > Ethanolamine + CL(16:1(9Z)/19:0cycv8c/14:0/14:0)
PE(19:0/17:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))
PG(14:0/14:0) + PE(15:0/17:0cycw7c) > CL(17:0cycw7c/15:0cyclo/14:0/14:0) + Ethanolamine
PE(19:0/16:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/18:1(9Z)/14:0/17:0cycw7c)
PE(19:0/17:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/18:1(9Z)/14:0/18:1(9Z))
PE(19:0/16:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/18:1(9Z)/17:0cycw7c/14:0)
PE(19:0/17:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/14:0)
PE(19:0/16:0) + PG(14:0/14:0) > Ethanolamine + CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/17:0cycw7c)
PE(19:0/17:0) + PG(14:0/14:0) > Ethanolamine + CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/18:1(9Z))
PE(19:0/16:0) + PG(14:0/14:0) > Ethanolamine + CL(17:0cycw7c/17:0cycw7c/14:0/19:0cycv8c)
PG(14:0/14:0) + PE(17:0/14:0) > Ethanolamine + CL(14:0/18:1(9Z)/14:0/17:0cycw7c)
PE(18:1(9Z)/19:iso) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/19:0cycv8c/14:0/14:0)
PE(18:1(9Z)/14:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(9Z)/14:0/14:0/14:0)
PG(14:0/14:0) + PE(18:1(9Z)/19:iso) > Ethanolamine + CL(18:1(9Z)/14:0/19:0cycv8c/14:0)
PE(19:iso/19:iso) + PG(14:0/14:0) > CL(19:0cycv8c/19:0cycv8c/14:0/14:0) + Ethanolamine
PG(14:0/14:0) + PE(17:0cycw7c/19:iso) > Ethanolamine + CL(19:0cycv8c/17:0cycw7c/14:0/14:0)
PE(17:0cycw7c/19:iso) + PG(14:0/14:0) > CL(17:0cycw7c/19:0cycv8c/14:0/14:0) + Ethanolamine
PG(14:0/14:0) > Glycerol + cardiolipin (tetratetradecanoyl, n-C14:0)
2 PG(14:0/14:0) > Glycerol + CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo)
2 PG(14:0/14:0) > Glycerol + CL(18:1(9Z)/15:0cyclo/15:0cyclo/14:0)
2 PG(14:0/14:0) > Glycerol + CL(18:1(9Z)/16:0/14:0/14:0)
2 PG(14:0/14:0) > Glycerol + CL(18:1(9Z)/16:1(9Z)/14:0/14:0)
2 PGP(14:0/14:0) + Water > PG(14:0/14:0) + Phosphate
PG(14:0/14:0) + PE(10:0/17:0cycw7c) > Ethanolamine + CL(10:0/17:0cycw7c/14:0/14:0)
PE(14:0(3-OH)/14:0(3-OH)) + PG(14:0/14:0) > Ethanolamine + CL(14:0(3-OH)/14:0(3-OH)/14:0/14:0)
PE(14:0(3-OH)/14:0) + PG(14:0/14:0) > Ethanolamine + CL(14:0(3-OH)/14:0/14:0/14:0)
PE(14:0(3-OH)/16:1(9Z)) + PG(14:0/14:0) > Ethanolamine + CL(14:0(3-OH)/16:1(9Z)/14:0/14:0)
PE(14:0/14:0(3-OH)) + PG(14:0/14:0) > Ethanolamine + CL(14:0/14:0(3-OH)/14:0/14:0)
PE(15:0/14:0(3-OH)) + PG(14:0/14:0) > Ethanolamine + CL(15:0/14:0(3-OH)/14:0/14:0)
PE(16:1(9Z)/10:0) + PG(14:0/14:0) > Ethanolamine + CL(16:1(9Z)/10:0/14:0/14:0)
PE(16:1(9Z)/14:0(3-OH)) + PG(14:0/14:0) > Ethanolamine + CL(16:1(9Z)/14:0(3-OH)/14:0/14:0)
PE(16:1(9Z)/19:0) + PG(14:0/14:0) > Ethanolamine + CL(16:1(9Z)/19:0/14:0/14:0)
PE(17:0/16:1(9Z)) + PG(14:0/14:0) > Ethanolamine + CL(17:0/16:1(9Z)/14:0/14:0)
PE(17:0cycw7c/10:0(3-OH)) + PG(14:0/14:0) > CL(17:0cycw7c/10:0(3-OH)/14:0/14:0) + Ethanolamine
PE(17:0cycw7c/10:0(3-OH)) + PG(14:0/14:0) > Ethanolamine + CL(17:0cycw7c/10:0/14:0/14:0)
PE(18:1(11Z)/17:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(11Z)/17:0/14:0/14:0)
PE(18:1(11Z)/19:0) + PG(14:0/14:0) > Ethanolamine + CL(18:1(11Z)/19:0/14:0/14:0)
More...

SMPDB Pathways:
phospholipid biosynthesis (CL(10:0/17:0cycw7c/14:0/14:0))PW001912 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(14:0(3-OH)/14:0(3-OH)/14:0/14:0))PW001936 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(14:0(3-OH)/14:0/14:0/14:0))PW001937 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(14:0(3-OH)/16:1(9Z)/14:0/14:0))PW001940 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(14:0/14:0(3-OH)/14:0/14:0))PW001944 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(14:0/15:0cyclo/17:0cycw7c/14:0)PW001030 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(15:0/14:0(3-OH)/14:0/14:0))PW001947 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(16:1(9Z)/10:0/14:0/14:0))PW001954 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(16:1(9Z)/14:0(3-OH)/14:0/14:0))PW001957 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(16:1(9Z)/19:0/14:0/14:0))PW001960 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(17:0/16:1(9Z)/14:0/14:0))PW001963 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(17:0cycw7c/10:0(3-OH)/14:0/14:0))PW001966 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(17:0cycw7c/10:0/14:0/14:0))PW001968 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(17:0cycw7c/19:0cycv8c/14:0/14:0))PW001475 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(11Z)/17:0/14:0/14:0))PW001978 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(11Z)/19:0/14:0/14:0))PW001979 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/14:0/14:0/14:0))PW001493 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/14:0/19:0cycv8c/14:0))PW001502 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(18:1(9Z)/19:0cycv8c/14:0/14:0))PW001211 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/17:0cycw7c/14:0/14:0))PW001397 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/14:0/14:0))PW001432 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:0/14:0/14:0)PW001031 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:0/14:0/19:0cycv8c)PW001035 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:0/19:0cycv8c/14:0)PW001038 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:1(9Z)/14:0/16:1(9Z))PW001039 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:1(9Z)/14:0/18:1(9Z))PW001040 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:1(9Z)/14:0/19:0cycv8c)PW001041 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:1(9Z)/18:1(9Z)/14:0)PW001042 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/16:1(9Z)/19:0cycv8c/14:0)PW001043 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/14:0/14:0)PW001044 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/14:0/17:0cycw7c)PW001045 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/14:0/18:1(9Z))PW001046 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/14:0/19:0cycv8c)PW001047 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/17:0cycw7c/14:0)PW001048 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/19:0cycv8c/14:0)PW001049 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/19:0cycv8c/14:0/17:0cycw7c)PW001050 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/19:0cycv8c/14:0/19:0cycv8c)PW001051 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(14:0/19:0cycv8c/17:0cycw7c/14:0)PW001052 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/14:0/14:0/17:0cycw7c)PW001053 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/14:0/14:0)PW001142 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/14:0/14:0/14:0)PW001204 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/14:0/14:0/19:0cycv8c)PW001208 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/14:0/18:1(9Z)/14:0)PW001216 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/14:0/19:0cycv8c/14:0)PW001218 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/16:1(9Z)/14:0/14:0)PW001293 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/18:1(9Z)/14:0/14:0)PW001355 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:0/19:0cycv8c/14:0/14:0)PW001382 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/14:0/16:1(9Z))PW001416 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/14:0/18:1(9Z))PW001417 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/14:0/19:0cycv8c)PW001418 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/16:1(9Z)/14:0)PW001419 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/18:1(9Z)/14:0)PW001425 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/19:0cycv8c/14:0)PW001429 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:0/14:0/14:0)PW001470 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/14:0/14:0)PW001510 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/14:0/14:0)PW001571 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/14:0/14:0)PW001615 ThumbThumb?image type=greyscaleThumb?image type=simple
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/14:0/14:0)PW001650 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:Not Available
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 ID5283512
Kegg IDNot Available
ChemSpider ID4446629
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Uniprot ID:
P07000
Molecular weight:
38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in phospholipase activity
Specific function:
Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membrane breakdown and cell death; is dormant in normal growing cells. Required for efficient secretion of bacteriocins
Gene Name:
pldA
Uniprot ID:
P0A921
Molecular weight:
33163
Reactions
Phosphatidylcholine + H(2)O = 2-acylglycerophosphocholine + a carboxylate.
Phosphatidylcholine + H(2)O = 1-acylglycerophosphocholine + a carboxylate.
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 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.
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Plays a role in lysophospholipid acylation. Transfers fatty acids to the 1-position via an enzyme-bound acyl-ACP intermediate in the presence of ATP and magnesium. Its physiological function is to regenerate phosphatidylethanolamine from 2-acyl-glycero-3-phosphoethanolamine (2-acyl-GPE) formed by transacylation reactions or degradation by phospholipase A1
Gene Name:
aas
Uniprot ID:
P31119
Molecular weight:
80699
Reactions
Acyl-[acyl-carrier-protein] + O-(2-acyl-sn-glycero-3-phospho)ethanolamine = [acyl-carrier-protein] + O-(1-beta-acyl-2-acyl-sn-glycero-3-phospho)ethanolamine.
ATP + an acid + [acyl-carrier-protein] = AMP + diphosphate + acyl-[acyl-carrier-protein].
General function:
Involved in nucleotide binding
Specific function:
Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:
msbA
Uniprot ID:
P60752
Molecular weight:
64460
General function:
Not Available
Specific function:
Not known; overproduction leads to camphor resistance and chromosome condensation
Gene Name:
crcA
Uniprot ID:
P37001
Molecular weight:
21770
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Affects resistance to the gyrase inhibitor novobiocin
Gene Name:
cls
Uniprot ID:
P0A6H8
Molecular weight:
54822
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.
General function:
Involved in catalytic activity
Specific function:
Catalyzes, in vitro, the phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Can also catalyze phosphatidyl group transfer to water to form phosphatidate. Catalyzes little, if any, cardiolipin synthesis in vivo, even when the expression level is very high
Gene Name:
ybhO
Uniprot ID:
P0AA84
Molecular weight:
47633
Reactions
2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.
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

Transporters

General function:
Involved in phospholipid transporter activity
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaB
Uniprot ID:
P64602
Molecular weight:
10680
General function:
Involved in nucleotide binding
Specific function:
Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:
msbA
Uniprot ID:
P60752
Molecular weight:
64460
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaD
Uniprot ID:
P64604
Molecular weight:
19576
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaE
Uniprot ID:
P64606
Molecular weight:
27863