Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015
twitter

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 , diacylglycerol and 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 , nitrate reduction X (periplasmic, dissimilatory) :
sn-glycerol 3-phosphate[in] + a ubiquinone[membrane] → glycerone phosphate[in] + an ubiquinol[membrane]

glycerol-3-phosphate to fumarate electron transfer , nitrate reduction IX (dissimilatory) :
sn-glycerol 3-phosphate + a menaquinone[inner membrane] → glycerone phosphate + a menaquinol[inner 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 + 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+
ADP-α-D-glucose + sn-glycerol 3-phosphate = 2-(α-D-glucopyranosyl)-sn-glycerol 3-phosphate + ADP + H+
22-carboxy-docosanoyl-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
22-hydroxy-docosanoyl-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+
β-D-glucopyranose + 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 [Baldwin78]

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: glycerol-2-phosphate cytidylyltransfrase , glycerophosphocholine cholinephosphodiesterase , fructose 1,6-bisphosphatase , 3-phytase


References

Baldwin78: Baldwin SA, Perham RN (1978). "Novel kinetic and structural properties of the class-I D-fructose 1,6-bisphosphate aldolase from Escherichia coli (Crookes' strain)." Biochem J 1978;169(3);643-52. PMID: 348198

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


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 19.0 on Sat Aug 29, 2015, biocyc11.