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 Solubility0.000281 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count36ChemAxon
Refractivity176.9 m3·mol-1ChemAxon
Polarizability79 Å3ChemAxon
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 Pw001912Pw001912 greyscalePw001912 simple
phospholipid biosynthesis (CL(14:0(3-OH)/14:0(3-OH)/14:0/14:0))PW001936 Pw001936Pw001936 greyscalePw001936 simple
phospholipid biosynthesis (CL(14:0(3-OH)/14:0/14:0/14:0))PW001937 Pw001937Pw001937 greyscalePw001937 simple
phospholipid biosynthesis (CL(14:0(3-OH)/16:1(9Z)/14:0/14:0))PW001940 Pw001940Pw001940 greyscalePw001940 simple
phospholipid biosynthesis (CL(14:0/14:0(3-OH)/14:0/14:0))PW001944 Pw001944Pw001944 greyscalePw001944 simple
phospholipid biosynthesis (CL(14:0/15:0cyclo/17:0cycw7c/14:0)PW001030 Pw001030Pw001030 greyscalePw001030 simple
phospholipid biosynthesis (CL(15:0/14:0(3-OH)/14:0/14:0))PW001947 Pw001947Pw001947 greyscalePw001947 simple
phospholipid biosynthesis (CL(16:1(9Z)/10:0/14:0/14:0))PW001954 Pw001954Pw001954 greyscalePw001954 simple
phospholipid biosynthesis (CL(16:1(9Z)/14:0(3-OH)/14:0/14:0))PW001957 Pw001957Pw001957 greyscalePw001957 simple
phospholipid biosynthesis (CL(16:1(9Z)/19:0/14:0/14:0))PW001960 Pw001960Pw001960 greyscalePw001960 simple
phospholipid biosynthesis (CL(17:0/16:1(9Z)/14:0/14:0))PW001963 Pw001963Pw001963 greyscalePw001963 simple
phospholipid biosynthesis (CL(17:0cycw7c/10:0(3-OH)/14:0/14:0))PW001966 Pw001966Pw001966 greyscalePw001966 simple
phospholipid biosynthesis (CL(17:0cycw7c/10:0/14:0/14:0))PW001968 Pw001968Pw001968 greyscalePw001968 simple
phospholipid biosynthesis (CL(17:0cycw7c/19:0cycv8c/14:0/14:0))PW001475 Pw001475Pw001475 greyscalePw001475 simple
phospholipid biosynthesis (CL(18:1(11Z)/17:0/14:0/14:0))PW001978 Pw001978Pw001978 greyscalePw001978 simple
phospholipid biosynthesis (CL(18:1(11Z)/19:0/14:0/14:0))PW001979 Pw001979Pw001979 greyscalePw001979 simple
phospholipid biosynthesis (CL(18:1(9Z)/14:0/14:0/14:0))PW001493 Pw001493Pw001493 greyscalePw001493 simple
phospholipid biosynthesis (CL(18:1(9Z)/14:0/19:0cycv8c/14:0))PW001502 Pw001502Pw001502 greyscalePw001502 simple
phospholipid biosynthesis (CL(18:1(9Z)/19:0cycv8c/14:0/14:0))PW001211 Pw001211Pw001211 greyscalePw001211 simple
phospholipid biosynthesis (CL(19:0cycv8c/17:0cycw7c/14:0/14:0))PW001397 Pw001397Pw001397 greyscalePw001397 simple
phospholipid biosynthesis (CL(19:0cycv8c/19:0cycv8c/14:0/14:0))PW001432 Pw001432Pw001432 greyscalePw001432 simple
phospholipid biosynthesis CL(14:0/16:0/14:0/14:0)PW001031 Pw001031Pw001031 greyscalePw001031 simple
phospholipid biosynthesis CL(14:0/16:0/14:0/19:0cycv8c)PW001035 Pw001035Pw001035 greyscalePw001035 simple
phospholipid biosynthesis CL(14:0/16:0/19:0cycv8c/14:0)PW001038 Pw001038Pw001038 greyscalePw001038 simple
phospholipid biosynthesis CL(14:0/16:1(9Z)/14:0/16:1(9Z))PW001039 Pw001039Pw001039 greyscalePw001039 simple
phospholipid biosynthesis CL(14:0/16:1(9Z)/14:0/18:1(9Z))PW001040 Pw001040Pw001040 greyscalePw001040 simple
phospholipid biosynthesis CL(14:0/16:1(9Z)/14:0/19:0cycv8c)PW001041 Pw001041Pw001041 greyscalePw001041 simple
phospholipid biosynthesis CL(14:0/16:1(9Z)/18:1(9Z)/14:0)PW001042 Pw001042Pw001042 greyscalePw001042 simple
phospholipid biosynthesis CL(14:0/16:1(9Z)/19:0cycv8c/14:0)PW001043 Pw001043Pw001043 greyscalePw001043 simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/14:0/14:0)PW001044 Pw001044Pw001044 greyscalePw001044 simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/14:0/17:0cycw7c)PW001045 Pw001045Pw001045 greyscalePw001045 simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/14:0/18:1(9Z))PW001046 Pw001046Pw001046 greyscalePw001046 simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/14:0/19:0cycv8c)PW001047 Pw001047Pw001047 greyscalePw001047 simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/17:0cycw7c/14:0)PW001048 Pw001048Pw001048 greyscalePw001048 simple
phospholipid biosynthesis CL(14:0/18:1(9Z)/19:0cycv8c/14:0)PW001049 Pw001049Pw001049 greyscalePw001049 simple
phospholipid biosynthesis CL(14:0/19:0cycv8c/14:0/17:0cycw7c)PW001050 Pw001050Pw001050 greyscalePw001050 simple
phospholipid biosynthesis CL(14:0/19:0cycv8c/14:0/19:0cycv8c)PW001051 Pw001051Pw001051 greyscalePw001051 simple
phospholipid biosynthesis CL(14:0/19:0cycv8c/17:0cycw7c/14:0)PW001052 Pw001052Pw001052 greyscalePw001052 simple
phospholipid biosynthesis CL(15:0cyclo/14:0/14:0/17:0cycw7c)PW001053 Pw001053Pw001053 greyscalePw001053 simple
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/14:0/14:0)PW001142 Pw001142Pw001142 greyscalePw001142 simple
phospholipid biosynthesis CL(16:0/14:0/14:0/14:0)PW001204 Pw001204Pw001204 greyscalePw001204 simple
phospholipid biosynthesis CL(16:0/14:0/14:0/19:0cycv8c)PW001208 Pw001208Pw001208 greyscalePw001208 simple
phospholipid biosynthesis CL(16:0/14:0/18:1(9Z)/14:0)PW001216 Pw001216Pw001216 greyscalePw001216 simple
phospholipid biosynthesis CL(16:0/14:0/19:0cycv8c/14:0)PW001218 Pw001218Pw001218 greyscalePw001218 simple
phospholipid biosynthesis CL(16:0/16:1(9Z)/14:0/14:0)PW001293 Pw001293Pw001293 greyscalePw001293 simple
phospholipid biosynthesis CL(16:0/18:1(9Z)/14:0/14:0)PW001355 Pw001355Pw001355 greyscalePw001355 simple
phospholipid biosynthesis CL(16:0/19:0cycv8c/14:0/14:0)PW001382 Pw001382Pw001382 greyscalePw001382 simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/14:0/16:1(9Z))PW001416 Pw001416Pw001416 greyscalePw001416 simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/14:0/18:1(9Z))PW001417 Pw001417Pw001417 greyscalePw001417 simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/14:0/19:0cycv8c)PW001418 Pw001418Pw001418 greyscalePw001418 simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/16:1(9Z)/14:0)PW001419 Pw001419Pw001419 greyscalePw001419 simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/18:1(9Z)/14:0)PW001425 Pw001425Pw001425 greyscalePw001425 simple
phospholipid biosynthesis CL(16:1(9Z)/14:0/19:0cycv8c/14:0)PW001429 Pw001429Pw001429 greyscalePw001429 simple
phospholipid biosynthesis CL(16:1(9Z)/16:0/14:0/14:0)PW001470 Pw001470Pw001470 greyscalePw001470 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/14:0/14:0)PW001510 Pw001510Pw001510 greyscalePw001510 simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/14:0/14:0)PW001571 Pw001571Pw001571 greyscalePw001571 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/14:0/14:0)PW001615 Pw001615Pw001615 greyscalePw001615 simple
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/14:0/14:0)PW001650 Pw001650Pw001650 greyscalePw001650 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