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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: sn-glycerol 3-phosphate

Synonyms: L-α-glycerophosphate, L-G3P, L-glycerol 3-phosphate, α-glycerophosphoric acid, α-glycerophosphate, D-glycerol 1-phosphate, glycerol 3-phosphate

Superclasses: glycerol 1-phosphate

Chemical Formula: C3H7O6P

Molecular Weight: 170.06 Daltons

Monoisotopic Molecular Weight: 172.01367453150002 Daltons

pKa 1: 2.15

pKa 2: 7.2

SMILES: C(OP([O-])(=O)[O-])C(O)CO

InChI: InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/p-2/t3-/m1/s1

InChIKey: InChIKey=AWUCVROLDVIAJX-GSVOUGTGSA-L

Unification Links: CAS:57-03-4 , ChEBI:57597 , ChemSpider:2939444 , HMDB:HMDB00126 , IAF1260:137383 , KEGG:C00093 , MetaboLights:MTBLC57597 , PubChem:7048686

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -258.0304 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

1,3-propanediol biosynthesis (engineered) :
sn-glycerol 3-phosphate + H2O → glycerol + phosphate

CDP-diacylglycerol biosynthesis I , triacylglycerol biosynthesis :
a long-chain acyl-CoA + sn-glycerol 3-phosphate → a 1-acyl-sn-glycerol 3-phosphate + coenzyme A

CDP-diacylglycerol biosynthesis II :
an acyl-[acyl-carrier protein] + sn-glycerol 3-phosphate → a 1-acyl-sn-glycerol 3-phosphate + a holo-[acyl-carrier protein]

CDP-diacylglycerol biosynthesis III :
sn-glycerol 3-phosphate + an acyl phosphate → a 1-acyl-sn-glycerol 3-phosphate + phosphate

glycerol degradation I , glycerol-3-phosphate shuttle , glycerol-3-phosphate to cytochrome bo oxidase electron transfer , glycerophosphodiester degradation :
sn-glycerol 3-phosphate[in] + an ubiquinone[CCO-OUT-CCO-IN] → dihydroxyacetone phosphate[in] + an ubiquinol[CCO-OUT-CCO-IN]

glycerol-3-phosphate to fumarate electron transfer :
sn-glycerol 3-phosphate + a menaquinone[inner membrane] → dihydroxyacetone phosphate + a menaquinol[inner membrane]

superpathway phosphatidate biosynthesis (yeast) :
sn-glycerol 3-phosphate + oleoyl-CoA → 1-oleyl-2-lyso-phosphatidate + coenzyme A

teichoic acid (poly-glycerol) biosynthesis :
sn-glycerol 3-phosphate + CTP + H+ → CDP-glycerol + diphosphate

Not in pathways:
sn-glycerol 3-phosphate[in] + an electron-transfer-related quinone[CCO-OUT-CCO-IN] → dihydroxyacetone phosphate[in] + an electron-transfer-related quinol[CCO-OUT-CCO-IN]
sn-glycerol 3-phosphate + oxygen → hydrogen peroxide + dihydroxyacetone phosphate


glycerol 1-phosphate + H2O → glycerol + phosphate

Reactions known to produce the compound:

CDP-diacylglycerol biosynthesis I , CDP-diacylglycerol biosynthesis II , CDP-diacylglycerol biosynthesis III :
sn-glycerol 3-phosphate + NAD(P)+ ← dihydroxyacetone phosphate + NAD(P)H + H+

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

phosphatidylcholine resynthesis via glycerophosphocholine :
sn-glycero-3-phosphocholine + H2O → sn-glycerol 3-phosphate + choline + H+

phosphatidylglycerol degradation :
an L-1-phosphatidyl-glycerol + H2O → a 1,2-diacyl-sn-glycerol + sn-glycerol 3-phosphate + H+

phospholipid remodeling (phosphatidylethanolamine, yeast) :
sn-glycero-3-phosphoethanolamine + H2O → sn-glycerol 3-phosphate + ethanolamine + H+

Not in pathways:
glycerol 1,2-cyclic phosphate + H2O → sn-glycerol 3-phosphate + H+
sn-glycero-3-phospho-1-inositol + H2O → myo-inositol + sn-glycerol 3-phosphate + H+
glycerophosphoglycerol + H2O → glycerol + sn-glycerol 3-phosphate + H+
glycerophosphoserine + H2O → sn-glycerol 3-phosphate + L-serine + H+
sn-glycerol 3-phosphate + NADP+ ← L-glyceraldehyde 3-phosphate + NADPH + H+

Reactions known to both consume and produce the compound:

1,3-propanediol biosynthesis (engineered) , glycerol-3-phosphate shuttle , superpathway phosphatidate biosynthesis (yeast) :
sn-glycerol 3-phosphate + NAD+ ↔ dihydroxyacetone phosphate + NADH + H+

cardiolipin biosynthesis I , cardiolipin biosynthesis II , cardiolipin biosynthesis III , phosphatidylglycerol biosynthesis I (plastidic) , phosphatidylglycerol biosynthesis II (non-plastidic) :
a CDP-diacylglycerol + sn-glycerol 3-phosphate ↔ CMP + an L-1-phosphatidylglycerol-phosphate + H+

glycerol degradation I :
glycerol + ATP ↔ sn-glycerol 3-phosphate + ADP + H+

In Reactions of unknown directionality:

Not in pathways:
glycerol + diphosphate = sn-glycerol 3-phosphate + phosphate + H+
CDP-glycerol + H2O = sn-glycerol 3-phosphate + CMP + 2 H+
C22:0-DCA-CoA + sn-glycerol 3-phosphate = 2-C22:0-DCA-LPA + coenzyme A
hexadecanedioyl-CoA + sn-glycerol 3-phosphate = sn-2-C16:0-DCA-LPA + coenzyme A
hexadecanedioyl-CoA + sn-glycerol 3-phosphate = 1-C16:0-α,ω-dicarboxyl-2-lysophosphatidate + coenzyme A
ω-hydroxy-C22:0-CoA + sn-glycerol 3-phosphate = 2-ω-hydroxy-C22:0-LPA + coenzyme A
docosanoyl-CoA + sn-glycerol 3-phosphate = 2-docosanoyl-glycerol 3-phosphate + coenzyme A
UDP-α-D-galactose + sn-glycerol 3-phosphate = 2-(α-D-galactosyl)-sn-glycerol 3-phosphate + UDP + H+
UDP-α-D-galactose + sn-glycerol 3-phosphate = α-D-galactosyl-(1,1')-sn-glycerol 3-phosphate + UDP + H+
an acyl-CoA + sn-glycerol 3-phosphate = a 2-acyl-sn-glycerol 3-phosphate + coenzyme A
sn-glycerol 3-phosphate + NADP+ = D-glyceraldehyde 3-phosphate + NADPH + H+
sn-glycerol 3-phosphate + ADP-α-D-glucose = ADP + 2-(β-D-glucosyl)-sn-glycerol 3-phosphate + H+
β-D-glucose + sn-glycerol 3-phosphate = β-D-glucose 6-phosphate + glycerol

In Transport reactions:
sn-glycerol 3-phosphate[extracellular space] + ATP + H2O ↔ sn-glycerol 3-phosphate[cytosol] + ADP + phosphate + H+ ,
sn-glycerol 3-phosphate[periplasmic space] + phosphate[cytosol]sn-glycerol 3-phosphate[cytosol] + phosphate[periplasmic space] ,
ATP + sn-glycerol 3-phosphate[periplasmic space] + H2O → ADP + sn-glycerol 3-phosphate[cytosol] + phosphate + H+

In Redox half-reactions:
dihydroxyacetone phosphate[in] + 2 H+[in] + 2 e-sn-glycerol 3-phosphate[in]

Enzymes activated by sn-glycerol 3-phosphate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: fructose bisphosphate aldolase

Enzymes inhibited by sn-glycerol 3-phosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: glycerol-3-phosphate dehydrogenase [Clark80a, Edgar78a] , glycerol kinase [Pettigrew90, Comment 1]

Inhibitor (Mechanism unknown) of: phosphatidylglycerophosphate synthase [Comment 2]


References

Clark80a: Clark D, Lightner V, Edgar R, Modrich P, Cronan JE, Bell RM (1980). "Regulation of phospholipid biosynthesis in Escherichia coli. Cloning of the structural gene for the biosynthetic sn-glycerol-3-phosphate dehydrogenase." J Biol Chem 255(2);714-7. PMID: 6985897

Edgar78a: Edgar JR, Bell RM (1978). "Biosynthesis in Escherichia coli of sn-glycerol 3-phosphate, a precursor of phospholipid. Kinetic characterization of wild type and feedback-resistant forms of the biosynthetic sn-glycerol-3-phosphate dehydrogenase." J Biol Chem 253(18);6354-63. PMID: 28326

Hirabayashi76: Hirabayashi T, Larson TJ, Dowhan W (1976). "Membrane-associated phosphatidylglycerophosphate synthetase from Escherichia coli: purification by substrate affinity chromatography on cytidine 5'-diphospho-1,2-diacyl-sn-glycerol sepharose." Biochemistry 1976;15(24);5205-11. PMID: 793612

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Pettigrew90: Pettigrew DW, Yu GJ, Liu Y (1990). "Nucleotide regulation of Escherichia coli glycerol kinase: initial-velocity and substrate binding studies." Biochemistry 1990;29(37);8620-7. PMID: 2148683


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Thu Nov 20, 2014, BIOCYC13B.