Record Information
Version2.0
Creation Date2012-05-31 10:21:35 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00131
Identification
Name:Glycerol
Description:Glycerol is an organic compound, also called glycerin or glycerine. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydrophilic hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. Metabolism of glycerol in E. coli, generally requires the presence of external electron acceptors. The respiratory pathways mediating this metabolic process involve a glycerol transporter (encoded by glpF), a glycerol kinase (encoded by glpK), and two respiratory glycerol-3-phosphate dehydrogenases (G3PDHs). Glycerol may also be metabolized fermentatively leading to the production of ethanol.
Structure
Thumb
Synonyms:
  • 1,2,3-Trihydroxypropane
  • 1,2,3-Trihydroxypropanol
  • Bulbold
  • Cristal
  • E 422
  • Emery 916
  • Glyceol Opthalgan
  • Glycerin
  • Glycerine
  • Glyceritol
  • Glycerol
  • Glycyl alcohol
  • Glyrol
  • Glysanin
  • IFP
  • Incorporation factor
  • Mackstat H 66
  • Osmoglyn
  • Pricerine 9091
  • Propanetriol
  • RG-S
  • Trihydroxypropane
  • Tryhydroxypropane
Chemical Formula:C3H8O3
Weight:Average: 92.0938
Monoisotopic: 92.047344122
InChI Key:PEDCQBHIVMGVHV-UHFFFAOYSA-N
InChI:InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2
CAS number:56-81-5
IUPAC Name:propane-1,2,3-triol
Traditional IUPAC Name:glycerol
SMILES:OCC(O)CO
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:0
Melting point:20
Experimental Properties:
PropertyValueSource
Water Solubility:1000.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-1.76 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1170.0 mg/mLALOGPS
logP-1.9ALOGPS
logP-1.8ChemAxon
logS1.1ALOGPS
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.52 m3·mol-1ChemAxon
Polarizability8.93 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2 PG(16:0/16:0) <> cardiolipin (tetrahexadecanoyl, n-C16:0) + Glycerol
2 PG(18:1(11Z)/18:1(11Z)) <> CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)) + Glycerol
2 PG(12:0/12:0) <> cardiolipin (tetradodecanoyl, n-C12:0) + Glycerol
2 PG(14:1(7Z)/14:1(7Z)) <> cardiolipin (tetratetradec-7-enoyl, n-C14:1) + Glycerol
2 PG(18:0/18:0) <> cardiolipin (tetraoctadecanoyl, n-C18:0) + Glycerol
2 PG(16:1(9Z)/16:1(9Z)) <> cardiolipin (tetrahexadec-9-enoyl, n-C16:1) + Glycerol
2 PG(14:0/14:0) <> cardiolipin (tetratetradecanoyl, n-C14:0) + Glycerol
D-Glyceraldehyde + Hydrogen ion + NADH <> Glycerol + NAD
Glycerol 3-phosphate + Water > Glycerol + Phosphate
Glycerophosphoglycerol + Water > Glycerol + Glycerol 3-phosphate + Hydrogen ion
Glycerol 2-phosphate + Water > Glycerol + Phosphate
Glycerophosphoglycerol + Water > Glycerol + Glycerol 3-phosphate + Hydrogen ion
Adenosine triphosphate + Glycerol <> ADP + Glycerol 3-phosphate + Hydrogen ion
Glycerol + NAD <> Dihydroxyacetone + Hydrogen ion + NADH
Glycerol 2-phosphate + Water > Glycerol + Phosphate
Adenosine triphosphate + Glycerol <> ADP + Glycerol 3-phosphate
Glycerol + NAD <> Dihydroxyacetone + NADH + Hydrogen ion
Galactosylglycerol + Water <> D-Galactose + Glycerol
2 Phosphatidylglycerol <> Cardiolipin + Glycerol
an L-1-phosphatidyl-glycerol <> a cardiolipin + Glycerol
Glycerol + NAD <> Dihydroxyacetone + NADH + Hydrogen ion
glycerol 1-phosphate + Water Glycerol + Phosphate
Water + Glycerol 2-phosphate > Phosphate + Glycerol
Glycerol + Adenosine triphosphate > Hydrogen ion + Glycerol 3-phosphate + ADP
2 Phosphatidylglycerol > diphosphatidylglycerol + Glycerol
Glycerol + NAD > Dihydroxyacetone + NADH
Adenosine triphosphate + Glycerol > ADP + Glycerol 3-phosphate
2 Phosphatidylglycerol > diphosphatidylglycerol + Glycerol
PS(14:0/18:1(11Z)) > Glycerol + a cardiolipin
PG(18:0/18:0) + PG(18:0/18:0) > Glycerol + CL(16:0/16:0/16:0/16:1(9Z))
PG(18:2(9Z,12Z)/18:2(9Z,12Z)) > CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) + Glycerol
2 PG(18:1(9Z)/18:1(9Z)) > Glycerol + CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))
PG(14:0(3-OH)/15:0) > Glycerol + CL(15:0cyclo/15:0cyclo/14:0/16:0)
PG(14:0/14:0) > Glycerol + cardiolipin (tetratetradecanoyl, n-C14:0)
PG(14:0/16:0) > CL(14:0/16:0/14:0/16:0) + Glycerol
2 PG(16:1(9Z)/16:1(9Z)) > Glycerol + cardiolipin (tetrahexadec-9-enoyl, n-C16:1)
PG(19:0cycv8c/19:iso) > Glycerol + CL(19:0cycv8c/19:0cycv8c/19:0cycv8c/19:0cycv8c)
PG(15:0/16:1) > Glycerol + CL(15:0cyclo/15:0cyclo/15:0cyclo/15:0cyclo)
2 PG(10:0/19:iso) > Glycerol + CL(19:0cycv8c/14:0/14:0/17:0cycw7c)
2 PG(10:0/19:iso) > Glycerol + CL(19:0cycv8c/14:0/17:0cycw7c/14:0)
2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/14:0/14:0/19:0cycv8c)
2 PG(16:0/14:0) > CL(19:0cycv8c/14:0/19:0cycv8c/14:0) + Glycerol
2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/15:0cyclo/15:0cyclo/17:0cycw7c)
2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/15:0cyclo/17:0cycw7c/15:0cyclo)
2 PG(10:0/19:iso) > Glycerol + CL(19:0cycv8c/17:0cycw7c/14:0/14:0)
2 PG(16:0/14:0) > Glycerol + CL(19:0cycv8c/19:0cycv8c/14:0/14:0)
2 PG(16:0/14:0) > Glycerol + CL(17:0cycw7c/18:1(9Z)/17:0cycw7c/14:0)
2 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/19:0cycv8c/14:0/14:0)
2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/14:0/14:0/18:1(9Z))
2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/14:0/17:0cycw7c/17:0cycw7c)
2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/14:0/18:1(9Z)/14:0)
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(16:0/14:0) > Glycerol + CL(18:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo)
2 PG(14:0/14:0) > Glycerol + CL(18:1(9Z)/16:0/14:0/14:0)
2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/16:0/14:0/16:0)
2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:0/14:0/18:1(9Z))
2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:0/18:1(9Z)/14:0)
2 PG(14:0/14:0) > Glycerol + CL(18:1(9Z)/16:1(9Z)/14:0/14:0)
2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/16:1(9Z)/14:0/16:1(9Z))
2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:1(9Z)/14:0/18:1(9Z))
2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/16:1(9Z)/16:1(9Z)/14:0)
2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/14:0)
2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/17:0cycw7c/14:0/17:0cycw7c)
2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/17:0cycw7c/17:0cycw7c/14:0)
2 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/18:1(9Z)/14:0/14:0)
2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/18:1(9Z)/14:0/16:0)
2 PG(16:0/14:0) > Glycerol + CL(18:1(9Z)/18:1(9Z)/14:0/16:1(9Z))
2 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/16:1(9Z)/14:0/17:0cycw7c)
2 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/14:0)
2 PG(16:0/14:0) > Glycerol + CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/16:1(9Z))
2 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/17:0cycw7c/14:0/16:0)
2 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/17:0cycw7c/14:0/16:1(9Z))
2 PG(16:0/14:0) > Glycerol + CL(17:0cycw7c/18:1(9Z)/14:0/17:0cycw7c)
2 PG(16:1(9Z)/12:0(3-OH)) > Glycerol + CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo)
2 PG(14:0(3-OH)/14:0) > Glycerol + CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo)
2 PG(18:1(9Z)/16:0) > Glycerol + CL(18:1(9Z)/16:0/18:1(9Z)/16:0)
2 PG(18:1(9Z)/16:1(9Z)) > Glycerol + CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))
Glycerol + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + Glycerol 3-phosphate + ADP
2 PG(10:0(3-OH)/10:0) > Glycerol + CL(10:0(3-OH)/10:0/10:0(3-OH)/10:0)
2 PG(10:0(3-OH)/12:0(3-OH)) > Glycerol + CL(10:0(3-OH)/12:0(3-OH)/10:0(3-OH)/12:0(3-OH))
2 PG(10:0(3-OH)/12:0) > Glycerol + CL(10:0(3-OH)/12:0/10:0(3-OH)/12:0)
2 PG(10:0(3-OH)/15:0cyclo) > CL(10:0(3-OH)/15:0cyclo/10:0(3-OH)/15:0cyclo) + Glycerol
2 PG(10:0(3-OH)/16:0) > CL(10:0(3-OH)/16:0/10:0(3-OH)/16:0) + Glycerol
2 PG(10:0(3-OH)/16:1(9Z)) > Glycerol + CL(10:0(3-OH)/16:1(9Z)/10:0(3-OH)/16:1(9Z))
2 PG(10:0(3-OH)/17:0cycw7c) > Glycerol + CL(10:0(3-OH)/17:0cycw7c/10:0(3-OH)/17:0cycw7c)
2 PG(10:0(3-OH)/19:0cycv8c) > Glycerol + CL(10:0(3-OH)/19:0cycv8c/10:0(3-OH)/19:0cycv8c)
2 PG(10:0(3-OH)/19:iso) > Glycerol + CL(10:0(3-OH)/19:iso/10:0(3-OH)/19:iso)
2 PG(10:0/10:0(3-OH)) > Glycerol + CL(10:0/10:0(3-OH)/10:0/10:0(3-OH))
2 PG(10:0/12:0(3-OH)) > Glycerol + CL(10:0/12:0(3-OH)/10:0/12:0(3-OH))
2 PG(12:0(3-OH)/10:0(3-OH)) > Glycerol + CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(3-OH))
2 PG(12:0(3-OH)/10:0) > Glycerol + CL(12:0(3-OH)/10:0/12:0(3-OH)/10:0)
2 PG(12:0(3-OH)/14:0(3-OH)) > CL(12:0(3-OH)/14:0(3-OH)/12:0(3-OH)/14:0(3-OH)) + Glycerol
2 PG(12:0(3-OH)/14:0) > Glycerol + CL(12:0(3-OH)/14:0/12:0(3-OH)/14:0)
2 PG(12:0(3-OH)/15:0) > CL(12:0(3-OH)/15:0/12:0(3-OH)/15:0) + Glycerol
2 PG(12:0(3-OH)/15:0cyclo) > Glycerol + CL(12:0(3-OH)/15:0cyclo/12:0(3-OH)/15:0cyclo)
2 PG(12:0(3-OH)/17:0cycw7c) > Glycerol + CL(12:0(3-OH)/17:0cycw7c/12:0(3-OH)/17:0cycw7c)
2 PG(12:0(3-OH)/18:1(9Z)) > Glycerol + CL(12:0(3-OH)/18:1(9Z)/12:0(3-OH)/18:1(9Z))
2 PG(12:0(3-OH)/19:0cycv8c) > Glycerol + CL(12:0(3-OH)/19:0cycv8c/12:0(3-OH)/19:0cycv8c)
2 PG(12:0(3-OH)/19:iso) > Glycerol + CL(12:0(3-OH)/19:iso/12:0(3-OH)/19:iso)
2 PG(12:0/10:0(3-OH)) > CL(12:0/10:0(3-OH)/12:0/10:0(3-OH)) + Glycerol
2 PG(12:0/12:0) > Glycerol + cardiolipin (tetradodecanoyl, n-C12:0)
2 PG(12:0/14:0(3-OH)) > Glycerol + CL(12:0/14:0(3-OH)/12:0/14:0(3-OH))
2 PG(12:0/19:iso) > Glycerol + CL(12:0/19:iso/12:0/19:iso)
2 PG(14:0(3-OH)/12:0(3-OH)) > CL(14:0(3-OH)/12:0(3-OH)/14:0(3-OH)/12:0(3-OH)) + Glycerol
2 PG(14:0(3-OH)/12:0) > Glycerol + CL(14:0(3-OH)/12:0/14:0(3-OH)/12:0)
2 PG(14:0(3-OH)/16:1(9Z)) > Glycerol + CL(14:0(3-OH)/16:1(9Z)/14:0(3-OH)/16:1(9Z))
2 PG(14:0(3-OH)/17:0cycw7c) > Glycerol + CL(14:0(3-OH)/17:0cycw7c/14:0(3-OH)/17:0cycw7c)
2 PG(14:0/12:0(3-OH)) > Glycerol + CL(14:0/12:0(3-OH)/14:0/12:0(3-OH))
2 PG(15:0/10:0(3-OH)) > Glycerol + CL(15:0/10:0(3-OH)/15:0/10:0(3-OH))
2 PG(15:0/12:0(3-OH)) > Glycerol + CL(15:0/12:0(3-OH)/15:0/12:0(3-OH))
2 PG(15:0cyclo/10:0(3-OH)) > Glycerol + CL(15:0cyclo/10:0(3-OH)/15:0cyclo/10:0(3-OH))
2 PG(16:0/10:0(3-OH)) > Glycerol + CL(16:0/10:0(3-OH)/16:0/10:0(3-OH))
2 PG(16:0/14:0(3-OH)) > Glycerol + CL(16:0/14:0(3-OH)/16:0/14:0(3-OH))
2 PG(16:1(9Z)/14:0(3-OH)) > Glycerol + CL(16:1(9Z)/14:0(3-OH)/16:1(9Z)/14:0(3-OH))
2 PG(17:0cycw7c/10:0(3-OH)) > Glycerol + CL(17:0cycw7c/10:0(3-OH)/17:0cycw7c/10:0(3-OH))
2 PG(17:0cycw7c/12:0(3-OH)) > Glycerol + CL(17:0cycw7c/12:0(3-OH)/17:0cycw7c/12:0(3-OH))
2 PG(17:0cycw7c/19:iso) > Glycerol + CL(17:0cycw7c/19:iso/17:0cycw7c/19:iso)
2 PG(18:1(11Z)/19:0) > Glycerol + CL(18:1(11Z)/19:0/18:1(11Z)/19:0)
2 PG(18:1(9Z)/12:0(3-OH)) > Glycerol + CL(18:1(9Z)/12:0(3-OH)/18:1(9Z)/12:0(3-OH))
2 PG(19:0/16:1(9Z)) > Glycerol + CL(19:0/16:1(9Z)/19:0/16:1(9Z))
2 PG(19:0/18:1(11Z)) > Glycerol + CL(19:0/18:1(11Z)/19:0/18:1(11Z))
2 PG(19:0cycv8c/10:0(3-OH)) > Glycerol + CL(19:0cycv8c/10:0(3-OH)/19:0cycv8c/10:0(3-OH))
2 PG(19:0cycv8c/12:0(3-OH)) > Glycerol + CL(19:0cycv8c/12:0(3-OH)/19:0cycv8c/12:0(3-OH))
2 PG(19:1(9Z)/16:1(9Z)) > Glycerol + CL(19:1(9Z)/16:1(9Z)/19:1(9Z)/16:1(9Z))
2 PG(19:iso/10:0(3-OH)) > Glycerol + CL(19:iso/10:0(3-OH)/19:iso/10:0(3-OH))
2 PG(19:iso/10:0) > Glycerol + CL(19:iso/10:0/19:iso/10:0)
2 PG(19:iso/12:0(3-OH)) > Glycerol + CL(19:iso/12:0(3-OH)/19:iso/12:0(3-OH))
2 PG(19:iso/12:0) > Glycerol + CL(19:iso/12:0/19:iso/12:0)
2 PG(19:iso/14:0(3-OH)) > Glycerol + CL(19:iso/14:0(3-OH)/19:iso/14:0(3-OH))
2 PG(19:iso/14:0) > Glycerol + CL(19:iso/14:0/19:iso/14:0)
2 PG(19:iso/19:iso) > Glycerol + CL(19:iso/19:iso/19:iso/19:iso)
2 PG(16:0/16:0) > Glycerol + CL(16:0/16:0/16:0/16:0)
2 PG(15:0cyclo/15:0cyclo) > Glycerol + CL(15:0cyclo/15:0cyclo/15:0cyclo/15:0cyclo)
2 PG(16:1(9Z)/19:0cycv8c) > CL(16:1(9Z)/19:0cycv8c/16:1(9Z)/19:0cycv8c) + Glycerol
2 PG(18:1(9Z)/15:0cyclo) > Glycerol + CL(18:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo)
More...

SMPDB Pathways:
Galactose metabolismPW000821 Pw000821Pw000821 greyscalePw000821 simple
Propanoate metabolismPW000940 Pw000940Pw000940 greyscalePw000940 simple
glycerol metabolismPW000914 Pw000914Pw000914 greyscalePw000914 simple
glycerol metabolism IIPW000915 Pw000915Pw000915 greyscalePw000915 simple
glycerol metabolism III (sn-glycero-3-phosphoethanolamine)PW000916 Pw000916Pw000916 greyscalePw000916 simple
glycerol metabolism IV (glycerophosphoglycerol)PW000917 Pw000917Pw000917 greyscalePw000917 simple
glycerol metabolism V (glycerophosphoserine)PW000918 Pw000918Pw000918 greyscalePw000918 simple
inner membrane transportPW000786 Pw000786Pw000786 greyscalePw000786 simple
phospholipid biosynthesis (CL(10:0(3-OH)/10:0/10:0(3-OH)/10:0))PW001899 Pw001899Pw001899 greyscalePw001899 simple
phospholipid biosynthesis (CL(10:0(3-OH)/12:0(3-OH)/10:0(3-OH)/12:0(3-OH)))PW001900 Pw001900Pw001900 greyscalePw001900 simple
phospholipid biosynthesis (CL(10:0(3-OH)/12:0/10:0(3-OH)/12:0))PW001901 Pw001901Pw001901 greyscalePw001901 simple
phospholipid biosynthesis (CL(10:0(3-OH)/15:0cyclo/10:0(3-OH)/15:0cyclo))PW001902 Pw001902Pw001902 greyscalePw001902 simple
phospholipid biosynthesis (CL(10:0(3-OH)/16:0/10:0(3-OH)/16:0))PW001904 Pw001904Pw001904 greyscalePw001904 simple
phospholipid biosynthesis (CL(10:0(3-OH)/16:1(9Z)/10:0(3-OH)/16:1(9Z)))PW001903 Pw001903Pw001903 greyscalePw001903 simple
phospholipid biosynthesis (CL(10:0(3-OH)/17:0cycw7c/10:0(3-OH)/17:0cycw7c))PW001906 Pw001906Pw001906 greyscalePw001906 simple
phospholipid biosynthesis (CL(10:0(3-OH)/19:0cycv8c/10:0(3-OH)/19:0cycv8c))PW001908 Pw001908Pw001908 greyscalePw001908 simple
phospholipid biosynthesis (CL(10:0(3-OH)/19:iso/10:0(3-OH)/19:iso))PW001909 Pw001909Pw001909 greyscalePw001909 simple
phospholipid biosynthesis (CL(10:0/10:0(3-OH)/10:0/10:0(3-OH)))PW001910 Pw001910Pw001910 greyscalePw001910 simple
phospholipid biosynthesis (CL(10:0/12:0(3-OH)/10:0/12:0(3-OH)))PW001911 Pw001911Pw001911 greyscalePw001911 simple
phospholipid biosynthesis (CL(12:0(3-OH)/10:0(3-OH)/12:0(3-OH)/10:0(3-OH)))PW001913 Pw001913Pw001913 greyscalePw001913 simple
phospholipid biosynthesis (CL(12:0(3-OH)/10:0/12:0(3-OH)/10:0))PW001914 Pw001914Pw001914 greyscalePw001914 simple
phospholipid biosynthesis (CL(12:0(3-OH)/14:0(3-OH)/12:0(3-OH)/14:0(3-OH)))PW001918 Pw001918Pw001918 greyscalePw001918 simple
phospholipid biosynthesis (CL(12:0(3-OH)/14:0/12:0(3-OH)/14:0))PW001919 Pw001919Pw001919 greyscalePw001919 simple
phospholipid biosynthesis (CL(12:0(3-OH)/15:0/12:0(3-OH)/15:0))PW001920 Pw001920Pw001920 greyscalePw001920 simple
phospholipid biosynthesis (CL(12:0(3-OH)/15:0cyclo/12:0(3-OH)/15:0cyclo))PW001921 Pw001921Pw001921 greyscalePw001921 simple
phospholipid biosynthesis (CL(12:0(3-OH)/17:0cycw7c/12:0(3-OH)/17:0cycw7c))PW001922 Pw001922Pw001922 greyscalePw001922 simple
phospholipid biosynthesis (CL(12:0(3-OH)/18:1(9Z)/12:0(3-OH)/18:1(9Z)))PW001924 Pw001924Pw001924 greyscalePw001924 simple
phospholipid biosynthesis (CL(12:0(3-OH)/19:0cycv8c/12:0(3-OH)/19:0cycv8c))PW001925 Pw001925Pw001925 greyscalePw001925 simple
phospholipid biosynthesis (CL(12:0(3-OH)/19:iso/12:0(3-OH)/19:iso))PW001926 Pw001926Pw001926 greyscalePw001926 simple
phospholipid biosynthesis (CL(12:0/10:0(3-OH)/12:0/10:0(3-OH)))PW001928 Pw001928Pw001928 greyscalePw001928 simple
phospholipid biosynthesis (CL(12:0/12:0/12:0/12:0))PW001930 Pw001930Pw001930 greyscalePw001930 simple
phospholipid biosynthesis (CL(12:0/14:0(3-OH)/12:0/14:0(3-OH)))PW001931 Pw001931Pw001931 greyscalePw001931 simple
phospholipid biosynthesis (CL(12:0/19:iso/12:0/19:iso))PW001933 Pw001933Pw001933 greyscalePw001933 simple
phospholipid biosynthesis (CL(14:0(3-OH)/12:0(3-OH)/14:0(3-OH)/12:0(3-OH)))PW001934 Pw001934Pw001934 greyscalePw001934 simple
phospholipid biosynthesis (CL(14:0(3-OH)/12:0/14:0(3-OH)/12:0))PW001935 Pw001935Pw001935 greyscalePw001935 simple
phospholipid biosynthesis (CL(14:0(3-OH)/16:1(9Z)/14:0(3-OH)/16:1(9Z)))PW001939 Pw001939Pw001939 greyscalePw001939 simple
phospholipid biosynthesis (CL(14:0(3-OH)/17:0cycw7c/14:0(3-OH)/17:0cycw7c))PW001941 Pw001941Pw001941 greyscalePw001941 simple
phospholipid biosynthesis (CL(14:0/12:0(3-OH)/14:0/12:0(3-OH)))PW001943 Pw001943Pw001943 greyscalePw001943 simple
phospholipid biosynthesis (CL(14:0/15:0cyclo/17:0cycw7c/14:0)PW001030 Pw001030Pw001030 greyscalePw001030 simple
phospholipid biosynthesis (CL(15:0/10:0(3-OH)/15:0/10:0(3-OH)))PW001945 Pw001945Pw001945 greyscalePw001945 simple
phospholipid biosynthesis (CL(15:0/12:0(3-OH)/15:0/12:0(3-OH)))PW001946 Pw001946Pw001946 greyscalePw001946 simple
phospholipid biosynthesis (CL(15:0cyclo/10:0(3-OH)/15:0cyclo/10:0(3-OH)))PW001948 Pw001948Pw001948 greyscalePw001948 simple
phospholipid biosynthesis (CL(15:0cyclo/15:0cyclo/18:1(9Z)/16:0)) 1442599180PW002016 Pw002016Pw002016 greyscalePw002016 simple
phospholipid biosynthesis (CL(16:0/10:0(3-OH)/16:0/10:0(3-OH)))PW001949 Pw001949Pw001949 greyscalePw001949 simple
phospholipid biosynthesis (CL(16:0/14:0(3-OH)/16:0/14:0(3-OH)))PW001951 Pw001951Pw001951 greyscalePw001951 simple
phospholipid biosynthesis (CL(16:0/16:0/16:0/16:0))PW002010 Pw002010Pw002010 greyscalePw002010 simple
phospholipid biosynthesis (CL(16:1(9Z)/14:0(3-OH)/16:1(9Z)/14:0(3-OH)))PW001958 Pw001958Pw001958 greyscalePw001958 simple
phospholipid biosynthesis (CL(16:1(9Z)/19:0cycv8c/16:1(9Z)/19:0cycv8c))PW002017 Pw002017Pw002017 greyscalePw002017 simple
phospholipid biosynthesis (CL(17:0cycw7c/10:0(3-OH)/17:0cycw7c/10:0(3-OH)))PW001967 Pw001967Pw001967 greyscalePw001967 simple
phospholipid biosynthesis (CL(17:0cycw7c/12:0(3-OH)/17:0cycw7c/12:0(3-OH)))PW001970 Pw001970Pw001970 greyscalePw001970 simple
phospholipid biosynthesis (CL(17:0cycw7c/19:iso/17:0cycw7c/19:iso))PW001973 Pw001973Pw001973 greyscalePw001973 simple
phospholipid biosynthesis (CL(18:1(11Z)/19:0/18:1(11Z)/19:0))PW001980 Pw001980Pw001980 greyscalePw001980 simple
phospholipid biosynthesis (CL(18:1(9Z)/12:0(3-OH)/18:1(9Z)/12:0(3-OH)))PW001982 Pw001982Pw001982 greyscalePw001982 simple
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/14:0/15:0cyclo) 5)PW001717 Pw001717Pw001717 greyscalePw001717 simple
phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/18:1(9Z)/15:0cyclo))PW001531 Pw001531Pw001531 greyscalePw001531 simple
phospholipid biosynthesis (CL(18:1(9Z)/16:0/18:1(9Z)/16:0))PW001588 Pw001588Pw001588 greyscalePw001588 simple
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z)))PW001621 Pw001621Pw001621 greyscalePw001621 simple
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/19:0cycv8c))PW001026 Pw001026Pw001026 greyscalePw001026 simple
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/19:0cycv8c)) 1440195714PW001034 Pw001034Pw001034 greyscalePw001034 simple
phospholipid biosynthesis (CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/19:0cycv8c)) 2PW001186 Pw001186Pw001186 greyscalePw001186 simple
phospholipid biosynthesis (CL(18:1/18:1/18:1/18:1))PW001027 Pw001027Pw001027 greyscalePw001027 simple
phospholipid biosynthesis (CL(19:0/16:1(9Z)/19:0/16:1(9Z)))PW001985 Pw001985Pw001985 greyscalePw001985 simple
phospholipid biosynthesis (CL(19:0/18:1(11Z)/19:0/18:1(11Z)))PW001987 Pw001987Pw001987 greyscalePw001987 simple
phospholipid biosynthesis (CL(19:0cycv8c/10:0(3-OH)/19:0cycv8c/10:0(3-OH)))PW001991 Pw001991Pw001991 greyscalePw001991 simple
phospholipid biosynthesis (CL(19:0cycv8c/12:0(3-OH)/19:0cycv8c/12:0(3-OH)))PW001993 Pw001993Pw001993 greyscalePw001993 simple
phospholipid biosynthesis (CL(19:1(9Z)/16:1(9Z)/19:1(9Z)/16:1(9Z)))PW001995 Pw001995Pw001995 greyscalePw001995 simple
phospholipid biosynthesis (CL(19:iso/10:0(3-OH)/19:iso/10:0(3-OH)))PW001997 Pw001997Pw001997 greyscalePw001997 simple
phospholipid biosynthesis (CL(19:iso/10:0/19:iso/10:0))PW001998 Pw001998Pw001998 greyscalePw001998 simple
phospholipid biosynthesis (CL(19:iso/12:0(3-OH)/19:iso/12:0(3-OH)))PW002000 Pw002000Pw002000 greyscalePw002000 simple
phospholipid biosynthesis (CL(19:iso/12:0/19:iso/12:0))PW002001 Pw002001Pw002001 greyscalePw002001 simple
phospholipid biosynthesis (CL(19:iso/14:0(3-OH)/19:iso/14:0(3-OH)))PW002004 Pw002004Pw002004 greyscalePw002004 simple
phospholipid biosynthesis (CL(19:iso/14:0/19:iso/14:0))PW002006 Pw002006Pw002006 greyscalePw002006 simple
phospholipid biosynthesis (CL(19:iso/19:iso/19:iso/19:iso))PW002009 Pw002009Pw002009 greyscalePw002009 simple
phospholipid biosynthesis CL(14:0/16:0/14:0/14:0)PW001031 Pw001031Pw001031 greyscalePw001031 simple
phospholipid biosynthesis CL(14:0/16:0/14:0/18:1(9Z))PW001033 Pw001033Pw001033 greyscalePw001033 simple
phospholipid biosynthesis CL(14:0/16:0/14:0/19:0cycv8c)PW001035 Pw001035Pw001035 greyscalePw001035 simple
phospholipid biosynthesis CL(14:0/16:0/16:1(9Z)/14:0)PW001036 Pw001036Pw001036 greyscalePw001036 simple
phospholipid biosynthesis CL(14:0/16:0/18:1(9Z)/14:0)PW001037 Pw001037Pw001037 greyscalePw001037 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)/14:0/18:1(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/14:0/16:1(9Z)/16:1(9Z))PW001054 Pw001054Pw001054 greyscalePw001054 simple
phospholipid biosynthesis CL(15:0cyclo/14:0/19:0cycv8c/19:0cycv8c)PW001058 Pw001058Pw001058 greyscalePw001058 simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:0/16:1(9Z))PW001063 Pw001063Pw001063 greyscalePw001063 simple
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/16:1(9Z))PW001068 Pw001068Pw001068 greyscalePw001068 simple
phospholipid biosynthesis CL(15:0cyclo/16:0/16:1(9Z)/16:1(9Z))PW001108 Pw001108Pw001108 greyscalePw001108 simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/14:0/16:1(9Z))PW001118 Pw001118Pw001118 greyscalePw001118 simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/15:0cyclo/16:1(9Z))PW001120 Pw001120Pw001120 greyscalePw001120 simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/14:0)PW001126 Pw001126Pw001126 greyscalePw001126 simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/15:0cyclo)PW001127 Pw001127Pw001127 greyscalePw001127 simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/16:0)PW001128 Pw001128Pw001128 greyscalePw001128 simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/16:1(9Z))PW001129 Pw001129Pw001129 greyscalePw001129 simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/18:1(9Z))PW001131 Pw001131Pw001131 greyscalePw001131 simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/19:0cycv8c)PW001132 Pw001132Pw001132 greyscalePw001132 simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/18:1(9Z)/16:1(9Z))PW001137 Pw001137Pw001137 greyscalePw001137 simple
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/19:0cycv8c/16:1(9Z))PW001140 Pw001140Pw001140 greyscalePw001140 simple
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/14:0/14:0)PW001142 Pw001142Pw001142 greyscalePw001142 simple
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/16:1(9Z)/16:1(9Z))PW001167 Pw001167Pw001167 greyscalePw001167 simple
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/18:1(9Z)/19:0cycv8c)PW001178 Pw001178Pw001178 greyscalePw001178 simple
phospholipid biosynthesis CL(15:0cyclo/18:1(9Z)/19:0cycv8c/18:1(9Z))PW001180 Pw001180Pw001180 greyscalePw001180 simple
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/14:0/19:0cycv8c)PW001183 Pw001183Pw001183 greyscalePw001183 simple
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/16:1(9Z)/16:1(9Z))PW001191 Pw001191Pw001191 greyscalePw001191 simple
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/18:1(9Z)/18:1(9Z))PW001196 Pw001196Pw001196 greyscalePw001196 simple
phospholipid biosynthesis CL(16:0/14:0/14:0/14:0)PW001204 Pw001204Pw001204 greyscalePw001204 simple
phospholipid biosynthesis CL(16:0/14:0/14:0/16:0)PW001205 Pw001205Pw001205 greyscalePw001205 simple
phospholipid biosynthesis CL(16:0/14:0/14:0/16:1(9Z))PW001206 Pw001206Pw001206 greyscalePw001206 simple
phospholipid biosynthesis CL(16:0/14:0/14:0/18:1(9Z))PW001207 Pw001207Pw001207 greyscalePw001207 simple
phospholipid biosynthesis CL(16:0/14:0/14:0/19:0cycv8c)PW001208 Pw001208Pw001208 greyscalePw001208 simple
phospholipid biosynthesis CL(16:0/14:0/16:0/14:0)PW001209 Pw001209Pw001209 greyscalePw001209 simple
phospholipid biosynthesis CL(16:0/14:0/16:1(9Z)/14:0)PW001213 Pw001213Pw001213 greyscalePw001213 simple
phospholipid biosynthesis CL(16:0/14:0/19:0cycv8c/14:0)PW001218 Pw001218Pw001218 greyscalePw001218 simple
phospholipid biosynthesis CL(16:0/15:0cyclo/16:1(9Z)/16:1(9Z))PW001235 Pw001235Pw001235 greyscalePw001235 simple
phospholipid biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(9Z))PW001313 Pw001313Pw001313 greyscalePw001313 simple
phospholipid biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:1(9Z))PW001329 Pw001329Pw001329 greyscalePw001329 simple
phospholipid biosynthesis CL(16:0/16:1(9Z)/19:0cycv8c/16:1(9Z))PW001336 Pw001336Pw001336 greyscalePw001336 simple
phospholipid biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:1(9Z))PW001362 Pw001362Pw001362 greyscalePw001362 simple
phospholipid biosynthesis CL(16:0/19:0cycv8c/14:0/14:0)PW001382 Pw001382Pw001382 greyscalePw001382 simple
phospholipid biosynthesis CL(16:0/19:0cycv8c/16:1(9Z)/16:1(9Z))PW001393 Pw001393Pw001393 greyscalePw001393 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)/15:0cyclo/14:0/16:1(9Z))PW001437 Pw001437Pw001437 greyscalePw001437 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:0/16:1(9Z))PW001449 Pw001449Pw001449 greyscalePw001449 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:1(9Z)/14:0)PW001450 Pw001450Pw001450 greyscalePw001450 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:1(9Z)/15:0cyclo)PW001451 Pw001451Pw001451 greyscalePw001451 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:1(9Z)/16:0)PW001452 Pw001452Pw001452 greyscalePw001452 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:1(9Z)/16:1(9Z))PW001453 Pw001453Pw001453 greyscalePw001453 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:1(9Z)/18:1(9Z))PW001455 Pw001455Pw001455 greyscalePw001455 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/16:1(9Z)/19:0cycv8c)PW001456 Pw001456Pw001456 greyscalePw001456 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/18:1(9Z)/16:1(9Z))PW001461 Pw001461Pw001461 greyscalePw001461 simple
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/19:0cycv8c/16:1(9Z))PW001468 Pw001468Pw001468 greyscalePw001468 simple
phospholipid biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(9Z))PW001489 Pw001489Pw001489 greyscalePw001489 simple
phospholipid biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/19:0cycv8c)PW001490 Pw001490Pw001490 greyscalePw001490 simple
phospholipid biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:1(9Z))PW001503 Pw001503Pw001503 greyscalePw001503 simple
phospholipid biosynthesis CL(16:1(9Z)/16:0/19:0cycv8c/16:1(9Z))PW001508 Pw001508Pw001508 greyscalePw001508 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/14:0/14:0)PW001510 Pw001510Pw001510 greyscalePw001510 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/14:0/15:0cyclo)PW001511 Pw001511Pw001511 greyscalePw001511 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/14:0/18:1(9Z))PW001521 Pw001521Pw001521 greyscalePw001521 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/14:0/19:0cycv8c)PW001522 Pw001522Pw001522 greyscalePw001522 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(9Z))PW001525 Pw001525Pw001525 greyscalePw001525 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/19:0cycv8c)PW001526 Pw001526Pw001526 greyscalePw001526 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/14:0)PW001544 Pw001544Pw001544 greyscalePw001544 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/15:0cyclo)PW001545 Pw001545Pw001545 greyscalePw001545 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:0)PW001546 Pw001546Pw001546 greyscalePw001546 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))PW001547 Pw001547Pw001547 greyscalePw001547 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))PW001549 Pw001549Pw001549 greyscalePw001549 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/19:0cycv8c)PW001550 Pw001550Pw001550 greyscalePw001550 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/19:0cycv8c/14:0)PW001551 Pw001551Pw001551 greyscalePw001551 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/19:0cycv8c/15:0cyclo)PW001552 Pw001552Pw001552 greyscalePw001552 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/19:0cycv8c/16:0)PW001553 Pw001553Pw001553 greyscalePw001553 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/19:0cycv8c/16:1(9Z))PW001554 Pw001554Pw001554 greyscalePw001554 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/19:0cycv8c/18:1(9Z))PW001556 Pw001556Pw001556 greyscalePw001556 simple
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/19:0cycv8c/19:0cycv8c)PW001557 Pw001557Pw001557 greyscalePw001557 simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/14:0/14:0)PW001571 Pw001571Pw001571 greyscalePw001571 simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/14:0/16:1(9Z))PW001572 Pw001572Pw001572 greyscalePw001572 simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/14:0)PW001574 Pw001574Pw001574 greyscalePw001574 simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:1(9Z))PW001576 Pw001576Pw001576 greyscalePw001576 simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/19:0cycv8c)PW001589 Pw001589Pw001589 greyscalePw001589 simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))PW001602 Pw001602Pw001602 greyscalePw001602 simple
phospholipid biosynthesis CL(16:1(9Z)/18:1(9Z)/19:0cycv8c/16:1(9Z))PW001606 Pw001606Pw001606 greyscalePw001606 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/14:0/14:0)PW001615 Pw001615Pw001615 greyscalePw001615 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/14:0/16:1(9Z))PW001616 Pw001616Pw001616 greyscalePw001616 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/16:1(9Z)/14:0)PW001624 Pw001624Pw001624 greyscalePw001624 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/16:1(9Z)/19:0cycv8c)PW001626 Pw001626Pw001626 greyscalePw001626 simple
phospholipid biosynthesis CL(16:1(9Z)/19:0cycv8c/19:0cycv8c/16:1(9Z))PW001641 Pw001641Pw001641 greyscalePw001641 simple
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/14:0/14:0)PW001650 Pw001650Pw001650 greyscalePw001650 simple
phospholipid biosynthesis I (18:0, 18:0)PW001001 Pw001001Pw001001 greyscalePw001001 simple
phospholipid biosynthesis I (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) )PW001025 Pw001025Pw001025 greyscalePw001025 simple
phospholipid biosynthesisCL(16:0/16:1(9Z)/16:1(9Z)/19:0cycv8c)PW001314 Pw001314Pw001314 greyscalePw001314 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fr2-0910000000-6497c0870b71585c6322View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0ktb-0920000000-93408d69acffad6f48afView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-05mk-0940000000-778ba583836705f8fdf4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00kb-0920000000-2e4b358941c660851f0aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dj-6920000000-6828d7b00cb31e84fac1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0le9-0940000000-e0b9bada9be26d720326View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-01qc-9000000000-80cdb8c006ea00f55a64View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-01ox-9000000000-3fe0c184a891364773a8View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0fr2-0930000000-470b6694b25fde40d80fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0fr2-0910000000-6497c0870b71585c6322View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0ktb-0920000000-93408d69acffad6f48afView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-05mk-0940000000-778ba583836705f8fdf4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00kb-0920000000-2e4b358941c660851f0aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00dj-6920000000-6828d7b00cb31e84fac1View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0le9-0940000000-e0b9bada9be26d720326View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00kb-0920000000-085a71f40d38f2729036View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0q4u-9280000000-1487e8921bcecbde6458View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9000000000-d7c139dc01453f61eb99View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9000000000-7d7844b4813b038012daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-9100000000-16029dbe79f139ab904aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-01ox-9000000000-3fe0c184a891364773a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-a638e26fe3c3f48563c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-9000000000-d3fd9e9abd911eb0f88eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-ca218dca3a5d86196d81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-b40367f5ca8d11288fbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-ba29a0647084e32d8704View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9000000000-4cd85379d414c16f95c0View in MoNA
MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-3706109441e6d3017895View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Berger C, Sakowitz OW, Kiening KL, Schwab S: Neurochemical monitoring of glycerol therapy in patients with ischemic brain edema. Stroke. 2005 Feb;36(2):e4-6. Epub 2004 Dec 23. Pubmed: 15618446
  • Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. Pubmed: 14708889
  • Bulow J, Gjeraa K, Enevoldsen LH, Simonsen L: Lipid mobilization from human abdominal, subcutaneous adipose tissue is independent of sex during steady-state exercise. Clin Physiol Funct Imaging. 2006 Jul;26(4):205-11. Pubmed: 16836692
  • Coppack SW, Chinkes DL, Miles JM, Patterson BW, Klein S: A multicompartmental model of in vivo adipose tissue glycerol kinetics and capillary permeability in lean and obese humans. Diabetes. 2005 Jul;54(7):1934-41. Pubmed: 15983192
  • de Araujo Burgos MG, Bion FM, Campos F: [Lactation and alcohol: clinical and nutritional effects] Arch Latinoam Nutr. 2004 Mar;54(1):25-35. Pubmed: 15332353
  • De Haene H, Taes Y, Christophe A, Delanghe J: Comparison of triglyceride concentration with lipemic index in disorders of triglyceride and glycerol metabolism. Clin Chem Lab Med. 2006;44(2):220-2. Pubmed: 16475911
  • Ekberg NR, Wisniewski N, Brismar K, Ungerstedt U: Measurement of glucose and metabolites in subcutaneous adipose tissue during hyperglycemia with microdialysis at various perfusion flow rates. Clin Chim Acta. 2005 Sep;359(1-2):53-64. Pubmed: 15939412
  • Eriksson A, Lindstedt S, Ransnas L, von Wendt L: Deficiency of glycerol kinase (EC 2.7.1.30). Clin Chem. 1983 Apr;29(4):718-22. Pubmed: 6299616
  • Fluhr JW, Mao-Qiang M, Brown BE, Wertz PW, Crumrine D, Sundberg JP, Feingold KR, Elias PM: Glycerol regulates stratum corneum hydration in sebaceous gland deficient (asebia) mice. J Invest Dermatol. 2003 May;120(5):728-37. Pubmed: 12713573
  • Foster KJ, Alberti KG, Hinks L, Lloyd B, Postle A, Smythe P, Turnell DC, Walton R: Blood intermediary metabolite and insulin concentrations after an overnight fast: reference ranges for adults, and interrelations. Clin Chem. 1978 Sep;24(9):1568-72. Pubmed: 688619
  • 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
  • Konig K, Rickels E, Heissler HE, Zumkeller M, Samii M: Artificial elevation of brain tissue glycerol by administration of a glycerol-containing agent. Case report. J Neurosurg. 2001 Apr;94(4):621-3. Pubmed: 11302662
  • Olbermann M, Grunert A, Bassler KH: [Biokinetic characterization of human glycerin utilization] Infusionsther Klin Ernahr. 1977 Apr;4(2):68-70. Pubmed: 558160
  • Pecora P, Suraci C, Antonelli M, De Maria S, Marrocco W: Blood glycerol meaning in obese patients. Boll Soc Ital Biol Sper. 1981 Dec 15;57(23):2389-93. Pubmed: 7337752
  • Quisth V, Enoksson S, Blaak E, Hagstrom-Toft E, Arner P, Bolinder J: Major differences in noradrenaline action on lipolysis and blood flow rates in skeletal muscle and adipose tissue in vivo. Diabetologia. 2005 May;48(5):946-53. Epub 2005 Mar 19. Pubmed: 15778861
  • Ross SE, Erickson RL, Gerin I, DeRose PM, Bajnok L, Longo KA, Misek DE, Kuick R, Hanash SM, Atkins KB, Andresen SM, Nebb HI, Madsen L, Kristiansen K, MacDougald OA: Microarray analyses during adipogenesis: understanding the effects of Wnt signaling on adipogenesis and the roles of liver X receptor alpha in adipocyte metabolism. Mol Cell Biol. 2002 Aug;22(16):5989-99. Pubmed: 12138207
  • Sjarif DR, Hellerud C, van Amstel JK, Kleijer WJ, Sperl W, Lacombe D, Sass JO, Beemer FA, Duran M, Poll-The BT: Glycerol kinase deficiency: residual activity explained by reduced transcription and enzyme conformation. Eur J Hum Genet. 2004 Jun;12(6):424-32. Pubmed: 15026783
  • Sjostrand M, Gudbjornsdottir S, Holmang A, Strindberg L, Ekberg K, Lonnroth P: Measurements of interstitial muscle glycerol in normal and insulin-resistant subjects. J Clin Endocrinol Metab. 2002 May;87(5):2206-11. Pubmed: 11994365
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. Pubmed: 8257730
  • Titov VN, Lisitsyn DM, Ameliushkina VA, Lupanov VP, Staroverov II, Osipov SG, Kukharchuk VV: [Double bonds of fatty acids, alcohols glycerol, cholesterol and nonpolar serum lipids. Diagnostic value of hypercholesterolemia] Klin Lab Diagn. 2002 May;(5):3-8. Pubmed: 12085703
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yaqoob M, Nabi A: Flow injection chemiluminescent assays for glycerol and triglycerides using a co-immobilized enzyme reactor. Luminescence. 2003 Mar-Apr;18(2):67-71. Pubmed: 12687625
Synthesis Reference:Yang, Yifang. Purification of glycerol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 3pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17754
HMDB IDHMDB00131
Pubchem Compound ID753
Kegg IDC00116
ChemSpider ID733
WikipediaGlycerol
BioCyc IDGLYCEROL
EcoCyc IDGLYCEROL
Ligand ExpoGOL

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal, non-reducing alpha-D- galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids
Gene Name:
melA
Uniprot ID:
P06720
Molecular weight:
50657
Reactions
Hydrolysis of terminal, non-reducing alpha-D-galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids.
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
glpQ
Uniprot ID:
P09394
Molecular weight:
40843
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Key enzyme in the regulation of glycerol uptake and metabolism
Gene Name:
glpK
Uniprot ID:
P0A6F3
Molecular weight:
56230
Reactions
ATP + glycerol = ADP + sn-glycerol 3-phosphate.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NAD-dependent oxidation of glycerol to dihydroxyacetone (glycerone). Allows microorganisms to utilize glycerol as a source of carbon under anaerobic conditions. In E.coli, an important role of gldA is also likely to regulate the intracellular level of dihydroxyacetone by catalyzing the reverse reaction, i.e. the conversion of dihydroxyacetone into glycerol. Possesses a broad substrate specificity, since it is also able to oxidize 1,2-propanediol and to reduce glycolaldehyde, methylglyoxal and hydroxyacetone into ethylene glycol, lactaldehyde and 1,2-propanediol, respectively
Gene Name:
gldA
Uniprot ID:
P0A9S5
Molecular weight:
38712
Reactions
Glycerol + NAD(+) = glycerone + NADH.
General function:
Involved in phosphatidylinositol phosphorylation
Specific function:
Myo-inositol phosphate + H(2)O = myo-inositol + phosphate
Gene Name:
suhB
Uniprot ID:
P0ADG4
Molecular weight:
29172
Reactions
Myo-inositol phosphate + H(2)O = myo-inositol + phosphate.
General function:
Involved in acid phosphatase activity
Specific function:
Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
Gene Name:
aphA
Uniprot ID:
P0AE22
Molecular weight:
26103
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
ugpQ
Uniprot ID:
P10908
Molecular weight:
27409
Reactions
A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in zinc ion binding
Specific function:
Has high formaldehyde dehydrogenase activity in the presence of glutathione and catalyzes the oxidation of normal alcohols in a reaction that is not GSH-dependent. In addition, hemithiolacetals other than those formed from GSH, including omega-thiol fatty acids, also are substrates
Gene Name:
frmA
Uniprot ID:
P25437
Molecular weight:
39359
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) = S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) = an aldehyde or ketone + NADH.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the hydrolysis of sugar phosphate to sugar and inorganic phosphate. Has a wide substrate specificity catalyzing the hydrolysis of fructose-1-P most efficiently, but it remains uncertain if this is the real substrate in vivo
Gene Name:
supH
Uniprot ID:
P75792
Molecular weight:
30413
Reactions
Sugar phosphate + H(2)O = sugar + phosphate.
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:
Not Available
Specific function:
Not Available
Gene Name:
yfbT
Uniprot ID:
P77625
Molecular weight:
Not Available

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
Transporter of glycerol across the cytoplasmic membrane, with limited permeability to water and small uncharged compounds such as polyols
Gene Name:
glpF
Uniprot ID:
P0AER0
Molecular weight:
29780
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368