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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

<i>sn</i>-glycerol 3-phosphate compound structure

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[membrane] → glycerone phosphate[in] + an ubiquinol[membrane]

oleate biosynthesis III (cyanobacteria) :
sn-glycerol 3-phosphate + a stearoyl-[acp] → 1-stearoyl-sn-glycerol 3-phosphate + a holo-[acyl-carrier protein]

stigma estolide biosynthesis :
18-hydroxyoleoyl-CoA + sn-glycerol 3-phosphate → 1-[18-hydroxyoleyl]-2-lyso-phosphatidate + coenzyme A

superpathway of 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 quinone[membrane] → glycerone phosphate[in] + an electron-transfer quinol[membrane]
sn-glycerol 3-phosphate + a menaquinone[inner membrane] → glycerone phosphate + a menaquinol[inner membrane]
sn-glycerol 3-phosphate + oxygen → hydrogen peroxide + glycerone phosphate

Not in pathways:
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)+ ← glycerone 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 of phosphatidate biosynthesis (yeast) :
sn-glycerol 3-phosphate + NAD+ ↔ glycerone 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:
glycerone phosphate[in] + 2 H+[in] + 2 e-[membrane]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 kinase [Pettigrew90, Comment 1] , glycerol-3-phosphate dehydrogenase [Clark80a, Edgar78]

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

This compound has been characterized as an alternative substrate of the following enzymes: 3-phytase , glycerophosphocholine cholinephosphodiesterase , glycerol-2-phosphate cytidylyltransfrase


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

Edgar78: 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


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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 19.0 on Mon Apr 27, 2015, BIOCYC14B.