Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000049
Identification
Name: Glycerol 3-phosphate
Description:Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. (Wikipedia).
Structure
Thumb
Synonyms:
  • α-glycerophosphate
  • α-glycerophosphoric acid
  • 1-(Dihydrogen phosphate) Glycerol
  • 1-(Dihydrogen phosphoric acid) glycerol
  • 1-Glycerophosphate
  • 1-Glycerophosphorate
  • 1-Glycerophosphoric acid
  • 3-Glycerophosphate
  • 3-Glycerophosphoric acid
  • A-Glycerophosphate
  • A-Glycerophosphorate
  • A-Glycerophosphoric acid
  • A-Phosphoglycerol
  • Alpha-Glycerophosphate
  • Alpha-Glycerophosphorate
  • Alpha-Glycerophosphoric acid
  • Alpha-Phosphoglycerol
  • D-Glycerol-1-phosphate
  • D-Glycerol-1-phosphoric acid
  • Dihydrogen a-glycerophosphate
  • Dihydrogen a-glycerophosphoric acid
  • Dihydrogen alpha-glycerophosphate
  • Dihydrogen alpha-glycerophosphoric acid
  • Dihydrogen α-glycerophosphate
  • Dihydrogen α-glycerophosphoric acid
  • DL-a-Glycerol phosphate
  • DL-a-Glycerol phosphoric acid
  • DL-a-Glycerophosphate
  • DL-a-Glycerophosphorate
  • DL-a-Glycerophosphoric acid
  • DL-a-Glyceryl phosphate
  • DL-a-Glyceryl phosphoric acid
  • DL-alpha-Glycerol phosphate
  • DL-alpha-Glycerol phosphoric acid
  • DL-alpha-Glycerophosphate
  • DL-alpha-Glycerophosphorate
  • DL-alpha-Glycerophosphoric acid
  • DL-alpha-Glyceryl phosphate
  • DL-alpha-Glyceryl phosphoric acid
  • DL-Glycerol 1-phosphate
  • DL-Glycerol 1-phosphoric acid
  • DL-Glycerol 3-phosphate
  • DL-Glycerol 3-phosphoric acid
  • DL-α-Glycerol phosphate
  • DL-α-Glycerol phosphoric acid
  • DL-α-Glycerophosphate
  • DL-α-Glycerophosphorate
  • DL-α-Glycerophosphoric acid
  • DL-α-Glyceryl phosphate
  • DL-α-Glyceryl phosphoric acid
  • Glycerol 1-phosphate
  • Glycerol 1-phosphoric acid
  • Glycerol 3-phosphoric acid
  • Glycerol a-phosphate
  • Glycerol a-phosphoric acid
  • Glycerol alpha-phosphate
  • Glycerol alpha-phosphoric acid
  • Glycerol monophosphate
  • Glycerol monophosphoric acid
  • Glycerol α-phosphate
  • Glycerol α-phosphoric acid
  • Glycerol-3-phosphate
  • Glycerol-3-phosphoric acid
  • Glycerophosphate
  • Glycerophosphate i
  • Glycerophosphorate
  • Glycerophosphorate I
  • Glycerophosphoric acid
  • Glycerophosphoric acid I
  • Glyceryl phosphate
  • Glyceryl phosphoric acid
  • Glyl3P
  • L-G3P
  • L-Glycerol 3-phosphate
  • L-Glycerol 3-phosphoric acid
  • Sn-glycerol 3-phosphate
  • sn-Glycerol 3-phosphoric acid
  • Sn-Gro-1-P
  • α-Glycerophosphate
  • α-Glycerophosphorate
  • α-Glycerophosphoric acid
  • α-Phosphoglycerol
Chemical Formula: C3H9O6P
Average Molecular Weight: 172.0737
Monoisotopic Molecular Weight: 172.013674532
InChI Key: AWUCVROLDVIAJX-GSVOUGTGSA-N
InChI:InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1
CAS number: 57-03-4
IUPAC Name:[(2R)-2,3-dihydroxypropoxy]phosphonic acid
Traditional IUPAC Name: 3-phosphoglycerol
SMILES:OC[C@@H](O)COP(O)(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as glycerophosphates. These are compounds containing a glycerol linked to a phosphate group.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphates
Direct Parent Glycerophosphates
Alternative Parents
Substituents
  • Sn-glycerol-3-phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Saccharide
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 102-104°CC
Experimental Properties:
PropertyValueSource
Water Solubility:1000.0 mg/mL [MERCK INDEX (1996)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility30.6 mg/mLALOGPS
logP-1.8ALOGPS
logP-2ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.39 m3·mol-1ChemAxon
Polarizability13.58 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Glycerol 3-phosphate + Ubiquinone-8 > Dihydroxyacetone phosphate + Ubiquinol-8
Dodecanoyl-ACP (n-C12:0ACP) + Glycerol 3-phosphate > 1-Dodecanoyl-sn-glycerol 3-phosphate + acyl carrier protein
Glycerol 3-phosphate + cis-hexadec-9-enoyl-[acyl-carrier protein] (n-C16:1) > 1-Hexadec-9-enoyl-sn-glycerol 3-phosphate + acyl carrier protein
Glycerol 3-phosphate + cis-octadec-11-enoyl-[acyl-carrier protein] (n-C18:1) > 1-Octadec-11-enoyl-sn-glycerol 3-phosphate + acyl carrier protein
Glycerol 3-phosphate + cis-tetradec-7-enoyl-[acyl-carrier protein] (n-C14:1) > 1-Tetradec-7-enoyl-sn-glycerol 3-phosphate + acyl carrier protein
Glycerol 3-phosphate + Myristoyl-ACP (n-C14:0ACP) > 1-Tetradecanoyl-sn-glycerol 3-phosphate + acyl carrier protein
Glycerol 3-phosphate + Octadecanoyl-ACP (n-C18:0ACP) > 1-Octadecanoyl-sn-glycerol 3-phosphate + acyl carrier protein
Glycerol 3-phosphate + Palmitoyl-ACP (n-C16:0ACP) > 1-hexadecanoyl-sn-glycerol 3-phosphate + acyl carrier protein
Glycerol 3-phosphate + Menaquinone 8 > Dihydroxyacetone phosphate + Menaquinol 8
2-Demethylmenaquinone 8 + Glycerol 3-phosphate > 2-Demethylmenaquinol 8 + Dihydroxyacetone phosphate
Adenosine triphosphate + Water + Glycerol 3-phosphate > ADP + Glycerol 3-phosphate + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Glycerol 3-phosphate > ADP + Glycerol 3-phosphate + Hydrogen ion + Phosphate
1-Dodecanoyl-sn-glycerol 3-phosphate + Water > Dodecanoate (N-C12:0) + Glycerol 3-phosphate + Hydrogen ion
1-hexadecanoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate + Hydrogen ion + Palmitic acid
1-Octadec-11-enoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate + Hydrogen ion + Octadecenoate (N-C18:1)
1-Octadecanoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate + Hydrogen ion + Octadecanoate (N-C18:0)
1-Tetradec-7-enoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate + Hydrogen ion + Tetradecenoate (N-C14:1)
1-Tetradecanoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate + Hydrogen ion + tetradecanoate (n-C14:0)
Glycerol 3-phosphate + Water > Glycerol + Phosphate
CDP-1,2-didodecanoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(12:0/12:0)
CDP-1,2-dihexadec-9-enoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(16:1(9Z)/16:1(9Z))
CDP-1,2-dihexadecanoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(16:0/16:0)
CDP-1,2-dioctadec-11-enoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(18:1(11Z)/18:1(11Z))
CDP-1,2-Dioctadecanoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(18:0/18:0)
CDP-1,2-ditetradec-7-enoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(14:1(7Z)/14:1(7Z))
CDP-1,2-ditetradecanoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(14:0/14:0)
Glycerylphosphorylethanolamine + Water > Ethanolamine + Glycerol 3-phosphate + Hydrogen ion
Glycerophosphoglycerol + Water > Glycerol + Glycerol 3-phosphate + Hydrogen ion
Glycerophosphoserine + Water > Glycerol 3-phosphate + Hydrogen ion + L-Serine
Sn-Glycero-3-phospho-1-inositol + Water > Glycerol 3-phosphate + Hydrogen ion + Inositol
Glycerol 3-phosphate + Hexadecanoyl-phosphate (n-C16:0) > 1-hexadecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Phosphate
Glycerol 3-phosphate + Octadecanoyl-phosphate (n-C18:0) > 1-Octadecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Phosphate
Glycerol 3-phosphate + Octadecanoyl-phosphate (n-C18:1) > 1-Octadec-11-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Phosphate
Glycerol 3-phosphate + Tetradecanoyl-phosphate (n-C14:0) > 1-Tetradecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Phosphate
Dodecanoly-phosphate (n-C12:0) + Glycerol 3-phosphate > 1-Dodecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Phosphate
Glycerophosphocholine + Water > Choline + Glycerol 3-phosphate + Hydrogen ion
Glycerol 3-phosphate + NADP <> Dihydroxyacetone phosphate + Hydrogen ion + NADPH
2-dodecanoyl-sn-glycerol 3-phosphate + Water > Dodecanoate (N-C12:0) + Glycerol 3-phosphate +2 Hydrogen ion
2-hexadecanoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate +2 Hydrogen ion + Palmitic acid
2-octadec-11-enoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate +2 Hydrogen ion + Octadecenoate (N-C18:1)
2-octadecanoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate +2 Hydrogen ion + Octadecanoate (N-C18:0)
2-tetradec-7-enoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate +2 Hydrogen ion + Tetradecenoate (N-C14:1)
2-tetradecanoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate +2 Hydrogen ion + tetradecanoate (n-C14:0)
Adenosine triphosphate + Glycerol <> ADP + Glycerol 3-phosphate + Hydrogen ion
Glycerol 3-phosphate + NAD <> Dihydroxyacetone phosphate + NADH + Hydrogen ion
Adenosine triphosphate + Glycerol <> ADP + Glycerol 3-phosphate
Glycerol 3-phosphate + FAD <> Dihydroxyacetone phosphate + FADH2
Glycerol 3-phosphate + Acyl-CoA + Acyl-CoA <> 1-Acyl-sn-glycerol 3-phosphate + Coenzyme A + 1-Acyl-sn-glycerol 3-phosphate
Glycerophosphocholine + Water <> Choline + Glycerol 3-phosphate
Glycerylphosphorylethanolamine + Water <> Ethanolamine + Glycerol 3-phosphate
CDP-diacylglycerol + Glycerol 3-phosphate <> Cytidine monophosphate + Phosphatidylglycerophosphate
Acyl-[acyl-carrier protein] + Glycerol 3-phosphate <> 1-Acyl-sn-glycerol 3-phosphate + Acyl-carrier protein
-->-->NAD(P)<sup>+</sup> + Glycerol 3-phosphate < NAD(P)H + Dihydroxyacetone phosphate + Hydrogen ion
a glycerophosphodiester + Water > an alcohol + Glycerol 3-phosphate + Hydrogen ion
a CDP-diacylglycerol + Glycerol 3-phosphate <> Cytidine monophosphate + an L-1-phosphatidylglycerol-phosphate + Hydrogen ion
a long-chain acyl-CoA + Glycerol 3-phosphate > a 1-acyl-<i>sn</i>-glycerol-3-phosphate + Coenzyme A
Glycerol 3-phosphate + a ubiquinone <> Dihydroxyacetone phosphate + a ubiquinol
an electron-transfer-related quinone + Glycerol 3-phosphate <> an electron-transfer-related quinol + Dihydroxyacetone phosphate
Glycerol 3-phosphate + NADP < Hydrogen ion + L-Glyceraldehyde 3-phosphate + NADPH
Glycerol 3-phosphate + a quinone > Dihydroxyacetone phosphate + a quinol
A glycerophosphodiester + Water > an alcohol + Glycerol 3-phosphate
Glycerol 3-phosphate + NAD(P)(+) > Dihydroxyacetone phosphate + NAD(P)H
Acyl-[acyl-carrier-protein] + Glycerol 3-phosphate > [acyl-carrier-protein] + 1-acyl-sn-glycerol 3-phosphate
Adenosine triphosphate + Water + Glycerol 3-phosphate > ADP + Inorganic phosphate + Glycerol 3-phosphate
Adenosine triphosphate + Water + Glycerol 3-phosphate > ADP + Inorganic phosphate + Glycerol 3-phosphate
Glycerol 3-phosphate + Quinone <> Dihydroxyacetone phosphate + Hydroquinone
Glycerophosphodiester + Water <> Alcohol + Glycerol 3-phosphate
Glycerol 3-phosphate + NAD + NADP <> Dihydroxyacetone phosphate + NADH + NADPH + Hydrogen ion
Dihydroxyacetone phosphate + Hydrogen ion + NADPH + NADPH > NADP + Glycerol 3-phosphate
Glycerol 3-phosphate + Ubiquinone-1 > Dihydroxyacetone phosphate + Ubiquinol-1
acyl-[acp] + Glycerol 3-phosphate > a holo-[acyl-carrier protein] + LPA(18:0/0:0)
long-chain fatty acyl-CoA + Glycerol 3-phosphate > Coenzyme A + LPA(18:0/0:0)
Glycerol 3-phosphate + Octadecenoyl-CoA (N-C18:1CoA) > LPA(18:1(9Z)/0:0) + Coenzyme A
Glycerol 3-phosphate + acyl-[acp] > a holo-[acyl-carrier protein]? + LPA(18:1(9Z)/0:0)
CDP-DG(16:0/16:0) + Glycerol 3-phosphate + CDP-DG(16:0/16:0) > Cytidine monophosphate + Hydrogen ion + PGP(16:0/16:0) + Cytidine monophosphate
Glycerol 3-phosphate + CDP-DG(16:0/16:1(9Z)) > Hydrogen ion + PGP(16:0/16:1(9Z)) + Cytidine monophosphate + Cytidine monophosphate
CDP-DG(16:0/18:1(11Z)) + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(16:0/18:1(11Z)) + Cytidine monophosphate
CDP-DG(16:1(9Z)/16:0) + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(16:1(9Z)/16:0) + Cytidine monophosphate
CDP-DG(18:1(11Z)/16:0) + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(18:1(11Z)/16:0) + Cytidine monophosphate
CDP-DG(18:1(11Z)/18:1(11Z)) + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(18:1(11Z)/18:1(11Z)) + Cytidine monophosphate
Glycerol 3-phosphate + CDP-1,2-Dioctadecanoylglycerol > Hydrogen ion + Cytidine monophosphate + PGP(18:0/18:0) + Cytidine monophosphate
CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + Glycerol 3-phosphate + CDP-DG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) > PGP(18:2(9Z,12Z)/18:2(9Z,12Z)) + Hydrogen ion + Cytidine monophosphate + Cytidine monophosphate
CDP-DG(19:1(9Z)/18:1(9Z)) + Glycerol 3-phosphate > Hydrogen ion + Cytidine monophosphate + PGP(18:1(9Z)/18:1(9Z)) + Cytidine monophosphate
CDP-DG(18:1(9Z)/18:0) + Glycerol 3-phosphate + CDP-DG(18:1(9Z)/18:0) > Hydrogen ion + Cytidine monophosphate + PGP(18:1(9Z)/18:1(9Z)) + Cytidine monophosphate
CDP-DG(19:1(9Z)/18:1(9Z)) + Glycerol 3-phosphate > PGP(16:0/16:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
CDP-DG(19:1(9Z)/18:1(9Z)) + Glycerol 3-phosphate > PGP(16:0/18:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
CDP-DG(19:1(9Z)/18:1(9Z)) + Glycerol 3-phosphate > PGP(14:0/14:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(18:1(9Z)/19:0cycv8c) + Glycerol 3-phosphate >2 PGP(18:1(9Z)/19:0cycv8c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(19:0cycv8c/15:0cyclo) + Glycerol 3-phosphate >2 PGP(19:0cycv8c/15:0cyclo) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(19:0cycv8c/16:0) + Glycerol 3-phosphate >2 PGP(19:0cycv8c/16:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(19:0cycv8c/16:1(9Z)) + Glycerol 3-phosphate >2 PGP(19:0cycv8c/16:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(14:0/17:0cycw7c) + Glycerol 3-phosphate >2 PGP(14:0/17:0cycw7c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(19:0cycv8c/18:1(9Z)) + Glycerol 3-phosphate >2 PGP(19:0cycv8c/18:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(14:0/16:0) + Glycerol 3-phosphate >2 PGP(14:0/16:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(19:0cycv8c/14:0) + Glycerol 3-phosphate >2 PGP(19:0cycv8c/14:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
Glycerol 3-phosphate + menaquinone-8 > Menaquinol 8 + Dihydroxyacetone phosphate
a glycerophosphodiester + Water > Hydrogen ion + Alcohol + Glycerol 3-phosphate
sn-glycero-3-phosphocholine + Water > Hydrogen ion + Benzyl alcohol + Glycerol 3-phosphate
sn-glycero-3-phosphoethanolamine + Water > Benzyl alcohol + Hydrogen ion + Glycerol 3-phosphate
Glycerophosphoglycerol + Water > Benzyl alcohol + Hydrogen ion + Glycerol 3-phosphate
glycerophosphoserine + Water > Hydrogen ion + Benzyl alcohol + Glycerol 3-phosphate
Glycerol + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + Glycerol 3-phosphate + ADP
2 CDP-DG(10:0(3-OH)/10:0) + Glycerol 3-phosphate >2 PGP(10:0(3-OH)/10:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(10:0(3-OH)/12:0(3-OH)) + Glycerol 3-phosphate >2 PGP(10:0(3-OH)/12:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(10:0(3-OH)/12:0) + Glycerol 3-phosphate >2 PGP(10:0(3-OH)/12:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(10:0(3-OH)/15:0cyclo) + Glycerol 3-phosphate >2 PGP(10:0(3-OH)/15:0cyclo) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(10:0(3-OH)/16:0) + Glycerol 3-phosphate >2 PGP(10:0(3-OH)/16:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(10:0(3-OH)/16:1(9Z)) + Glycerol 3-phosphate > PGP(10:0(3-OH)/16:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(10:0(3-OH)/17:0cycw7c) + Glycerol 3-phosphate >2 PGP(10:0(3-OH)/17:0cycw7c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(10:0(3-OH)/19:0cycv8c) + Glycerol 3-phosphate >2 PGP(10:0(3-OH)/19:0cycv8c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(10:0(3-OH)/19:iso) + Glycerol 3-phosphate >2 PGP(10:0(3-OH)/19:iso) + Cytidine triphosphate + Hydrogen ion
2 CDP-DG(10:0/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(10:0/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(10:0/12:0(3-OH)) + Glycerol 3-phosphate >2 PGP(10:0/12:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-1,2-ditetradecanoylglycerol + Glycerol 3-phosphate >2 PGP(14:0/14:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0(3-OH)/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0(3-OH)/10:0) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/10:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-1,2-didodecanoylglycerol + Glycerol 3-phosphate >2 PGP(12:0/12:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0(3-OH)/14:0(3-OH)) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/14:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0(3-OH)/14:0) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/14:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0(3-OH)/15:0) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/15:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0(3-OH)/15:0cyclo) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/15:0cyclo) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0(3-OH)/17:0cycw7c) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/17:0cycw7c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0(3-OH)/18:1(9Z)) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/18:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0(3-OH)/19:0cycv8c) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/19:0cycv8c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0(3-OH)/19:iso) + Glycerol 3-phosphate >2 PGP(12:0(3-OH)/19:iso) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(12:0/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0/14:0(3-OH)) + Glycerol 3-phosphate >2 PGP(12:0/14:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(12:0/19:iso) + Glycerol 3-phosphate >2 PGP(12:0/19:iso) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(14:0(3-OH)/12:0(3-OH)) + Glycerol 3-phosphate >2 PGP(14:0(3-OH)/12:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(14:0(3-OH)/12:0) + Glycerol 3-phosphate >2 PGP(14:0(3-OH)/12:0) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(14:0(3-OH)/16:1(9Z)) + Glycerol 3-phosphate >2 PGP(14:0(3-OH)/16:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(14:0(3-OH)/17:0cycw7c) + Glycerol 3-phosphate >2 PGP(14:0(3-OH)/17:0cycw7c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(14:0/12:0(3-OH)) + Glycerol 3-phosphate >2 PGP(14:0/12:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(15:0/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(15:0/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(15:0/12:0(3-OH)) + Glycerol 3-phosphate >2 PGP(15:0/12:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(15:0cyclo/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(15:0cyclo/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(16:0/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(16:0/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(16:0/14:0(3-OH)) + Glycerol 3-phosphate >2 PGP(16:0/14:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(16:1(9Z)/14:0(3-OH)) + Glycerol 3-phosphate >2 PGP(16:1(9Z)/14:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(16:1(9Z)/17:0cycw7c) + Glycerol 3-phosphate >2 PGP(16:1(9Z)/17:0cycw7c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(17:0cycw7c/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(17:0cycw7c/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(17:0cycw7c/12:0(3-OH)) + Glycerol 3-phosphate >2 PGP(17:0cycw7c/12:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(17:0cycw7c/19:iso) + Glycerol 3-phosphate >2 PGP(17:0cycw7c/19:iso) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(18:1(9Z)/12:0(3-OH)) + Glycerol 3-phosphate >2 PGP(18:1(9Z)/12:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(19:0/16:1(9Z)) + Glycerol 3-phosphate >2 PGP(19:0/16:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(19:0/18:1(11Z)) + Glycerol 3-phosphate >2 PGP(19:0/18:1(11Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(19:0cycv8c/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(19:0cycv8c/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(19:0cycv8c/12:0(3-OH)) + Glycerol 3-phosphate >2 PGP(19:0cycv8c/12:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
2 CDP-DG(19:1(9Z)/16:1(9Z)) + Glycerol 3-phosphate >2 PGP(19:1(9Z)/16:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphate
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-9200000000-bf06c1d1e56cb8853243View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9200000000-ffce45222cab00a0c302View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001j-9000000000-7689cca8f9c9a12d9e75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0902000000-00e3a7e1ee10fbd8b03eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-1a40c90fd2eb656ddf5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-9000000000-f9bc5f552db38767c437View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0920000000-72f8b96355726dd3a5b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0901000000-2c3a8ed438d7ca0fa049View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-a3549fb5ec2675fbf615View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-9000000000-096e2ba9a6ef6fd20d88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0930000000-171708905bad289d6031View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0925110000-c1ced10d34f533b3fa1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-4ee8a36492a451beda75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9000000000-de2aacfb81476c7755e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-dd342482ade09e9ce749View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0fkc-0917520000-d61e6034525ac5f7588dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9000000000-d537d3f23f3d9a789c20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-2f1ca45b50402f6e62dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0009000000-5606781224d6ab5caed3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0pi0-1900000000-75b6ed57a4c9cd6378b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a59-6900000000-1c46fbda1468f6fd803cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a5c-9400000000-305e9a2554d8c3274f32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-007o-9000000000-d11ad04a048c3dca25deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00mo-9000000000-7b779b4be184b5b26b6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Guminski T: Some glycolytic enzymes in normal cerebrospinal fluid, brain tissue and blood plasma of infants. Clin Chim Acta. 1976 Aug 16;71(1):61-6. Pubmed: 134854
  • 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
  • Slomiany BL, Piotrowski J, Mojtahed H, Slomiany A: Ebrotidine effect on the proteolytic and lipolytic activities of Helicobacter pylori. Gen Pharmacol. 1992 Mar;23(2):203-6. Pubmed: 1639232
  • 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
  • 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
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • 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
Synthesis Reference: Rios-Mercadillo, Victor M.; Whitesides, George M. Enzymic synthesis of sn-glycerol 3-phosphate. Journal of the American Chemical Society (1979), 101(19), 5828-9.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15978
HMDB IDHMDB00126
Pubchem Compound ID439162
Kegg IDC00093
ChemSpider ID388308
WikipediaGlycerol 3-phosphate
BioCyc IDGLYCEROL-3P
EcoCyc IDGLYCEROL-3P
Ligand ExpoGP9

Enzymes

General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Locus Tag:
PA5089
Molecular weight:
83.4 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:
glpQ
Locus Tag:
PA0347
Molecular weight:
42 kDa
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
Locus Tag:
PA3582
Molecular weight:
56 kDa
Reactions
ATP + glycerol = ADP + sn-glycerol 3-phosphate.
General function:
Involved in oxidation-reduction process
Specific function:
sn-glycerol 3-phosphate + NAD(P)(+) = glycerone phosphate + NAD(P)H
Gene Name:
gpsA
Locus Tag:
PA1614
Molecular weight:
36.8 kDa
Reactions
sn-glycerol 3-phosphate + NAD(P)(+) = glycerone phosphate + NAD(P)H.
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Catalyzes the transfer of an acyl group from acyl-ACP to glycerol-3-phosphate (G3P) to form lysophosphatidic acid (LPA). This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:
plsB
Locus Tag:
PA3673
Molecular weight:
94.8 kDa
Reactions
Acyl-CoA + sn-glycerol 3-phosphate = CoA + 1-acyl-sn-glycerol 3-phosphate.
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
This protein catalyzes the committed step to the synthesis of the acidic phospholipids
Gene Name:
pgsA
Locus Tag:
PA2584
Molecular weight:
20.5 kDa
Reactions
CDP-diacylglycerol + sn-glycerol 3-phosphate = CMP + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphate.
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:
tesA
Locus Tag:
PA2856
Molecular weight:
21 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Locus Tag:
PA3187
Molecular weight:
42.2 kDa
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
General function:
Involved in oxidoreductase activity
Specific function:
Conversion of glycerol 3-phosphate to dihydroxyacetone. Uses molecular oxygen or nitrate as electron acceptor
Gene Name:
glpD
Locus Tag:
PA3584
Molecular weight:
57.1 kDa
Reactions
sn-glycerol 3-phosphate + a quinone = glycerone phosphate + a quinol.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reversible formation of acyl-phosphate (acyl-PO(4)) from acyl-[acyl-carrier-protein] (acyl-ACP). This enzyme utilizes acyl-ACP as fatty acyl donor, but not acyl-CoA
Gene Name:
plsX
Locus Tag:
PA2969
Molecular weight:
34.6 kDa
Reactions
Acyl-[acyl-carrier-protein] + phosphate = acyl-phosphate + [acyl-carrier-protein].
General function:
Involved in fatty acid biosynthetic process
Specific function:
Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:
acpP
Locus Tag:
PA2966
Molecular weight:
8.7 kDa

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Locus Tag:
PA3187
Molecular weight:
42.2 kDa
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
General function:
Involved in glycerol-3-phosphate transmembrane transporter activity
Specific function:
Responsible for glycerol-3-phosphate uptake
Gene Name:
glpT
Locus Tag:
PA5235
Molecular weight:
49.3 kDa