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MetaCyc Compound: D-glyceraldehyde 3-phosphate

Synonyms: 3-phosphoglyceraldehyde, D-glyceraldehyde-3-P, glyceraldehyde 3-phosphate, GAP, glyceraldehyde-phosphate, glyceraldehyde-P, glyceraldehyde-3-P, (2R)-2-hydroxy-3-(phosphonooxy)-propanal, triose phosphate

Superclasses: all carbohydrates a carbohydrate a glycan a carbohydrate derivative an aldose phosphate DL-glyceraldehyde 3-phosphate

Chemical Formula: C3H5O6P

Molecular Weight: 168.04 Daltons

Monoisotopic Molecular Weight: 169.9980244673 Daltons

SMILES: [CH](=O)C(O)COP(=O)([O-])[O-]

InChI: InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)/p-2/t3-/m0/s1

InChIKey: InChIKey=LXJXRIRHZLFYRP-VKHMYHEASA-L

Unification Links: CAS:591-57-1 , ChEBI:59776 , HMDB:HMDB01112 , IAF1260:35637 , KEGG:C00118 , PubChem:24794350

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -265.65268 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

3-dehydroquinate biosynthesis II (archaea) , lactate biosynthesis (archaea) :
D-glyceraldehyde 3-phosphate → enolaldehyde + phosphate

clavulanate biosynthesis :
D-glyceraldehyde 3-phosphate + L-arginine → L-N2-(2-carboxyethyl)arginine + phosphate + H+

Entner-Doudoroff pathway III (semi-phosphorylative) :
D-glyceraldehyde 3-phosphate + NAD+ + H2O → 3-phospho-D-glycerate + NADH + 2 H+

glycolysis IV (plant cytosol) :
D-glyceraldehyde 3-phosphate + NADP+ + H2O → 3-phospho-D-glycerate + NADPH + 2 H+

methylerythritol phosphate pathway I , methylerythritol phosphate pathway II , pyridoxal 5'-phosphate biosynthesis I , thiazole biosynthesis I (E. coli) , thiazole biosynthesis II (Bacillus) :
pyruvate + D-glyceraldehyde 3-phosphate + H+ → 1-deoxy-D-xylulose 5-phosphate + CO2

pyridoxal 5'-phosphate biosynthesis II :
keto-D-ribose 5-phosphate + D-glyceraldehyde 3-phosphate + L-glutamine → pyridoxal 5'-phosphate + L-glutamate + phosphate + 3 H2O + H+

Reactions known to produce the compound:

3-dehydroquinate biosynthesis II (archaea) :
fructose 1,6-bisphosphate + methylglyoxal → 6-deoxy-5-ketofructose 1-phosphate + D-glyceraldehyde 3-phosphate

5-dehydro-4-deoxy-D-glucuronate degradation , D-fructuronate degradation , D-glucosaminate degradation , Entner-Doudoroff pathway I , Entner-Doudoroff pathway III (semi-phosphorylative) :
2-dehydro-3-deoxy-D-gluconate 6-phosphate → D-glyceraldehyde 3-phosphate + pyruvate

Bifidobacterium shunt , heterolactic fermentation :
D-xylulose 5-phosphate + phosphate → D-glyceraldehyde 3-phosphate + acetyl phosphate + H2O

Calvin-Benson-Bassham cycle :
D-glyceraldehyde 3-phosphate + NADP+ + phosphate ← 1,3-bisphospho-D-glycerate + NADPH + H+

formaldehyde assimilation III (dihydroxyacetone cycle) :
formaldehyde + D-xylulose 5-phosphate → dihydroxyacetone + D-glyceraldehyde 3-phosphate

methylthiolincosamide biosynthesis :
D-ribose 5-phosphate + D-fructose 6-phosphate → D-glycero-D-altro-octulose 8-phosphate + D-glyceraldehyde 3-phosphate

paspaline biosynthesis :
geranylgeranyl diphosphate + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate → 3-geranylgeranylindole + D-glyceraldehyde 3-phosphate + diphosphate

sucrose degradation V (sucrose α-glucosidase) :
D-glyceraldehyde + ATP → D-glyceraldehyde 3-phosphate + ADP + H+

Not in pathways:
(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine → L-tryptophan + D-glyceraldehyde 3-phosphate + H2O


an N-acetyl-β-D-galactosalaminyl-[glycan] + H2O → a glycan + N-acetyl-β-D-galactosamine

Reactions known to both consume and produce the compound:

1,3-propanediol biosynthesis (engineered) :
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate

2'-deoxy-α-D-ribose 1-phosphate degradation :
2-deoxy-D-ribose 5-phosphate ↔ acetaldehyde + D-glyceraldehyde 3-phosphate

Bifidobacterium shunt :
D-sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate ↔ D-ribose 5-phosphate + D-xylulose 5-phosphate
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
D-glyceraldehyde 3-phosphate + D-sedoheptulose 7-phosphate ↔ β-D-fructofuranose 6-phosphate + D-erythrose 4-phosphate

Calvin-Benson-Bassham cycle :
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate ↔ D-ribose 5-phosphate + D-xylulose 5-phosphate
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

D-galactonate degradation , L-glucose degradation :
2-dehydro-3-deoxy-D-galactonate 6-phosphate ↔ D-glyceraldehyde 3-phosphate + pyruvate

D-galactosamine and N-acetyl-D-galactosamine degradation , galactitol degradation , lactose and galactose degradation I , N-acetyl-D-galactosamine degradation :
D-tagatofuranose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate

DIBOA-glucoside biosynthesis , tryptophan biosynthesis :
(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate ↔ indole + D-glyceraldehyde 3-phosphate

formaldehyde assimilation II (RuMP Cycle) :
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate ↔ D-ribose 5-phosphate + D-xylulose 5-phosphate
D-glyceraldehyde 3-phosphate + D-sedoheptulose 7-phosphate ↔ β-D-fructofuranose 6-phosphate + D-erythrose 4-phosphate

formaldehyde assimilation III (dihydroxyacetone cycle) :
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate ↔ D-ribose 5-phosphate + D-xylulose 5-phosphate
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate
D-glyceraldehyde 3-phosphate + D-sedoheptulose 7-phosphate ↔ β-D-fructofuranose 6-phosphate + D-erythrose 4-phosphate

gluconeogenesis I :
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

gluconeogenesis II (Methanobacterium thermoautotrophicum) :
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + 2 an oxidized ferredoxin + H2O ↔ 3-phospho-D-glycerate + 2 a reduced ferredoxin + 2 H+
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

gluconeogenesis III :
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

glycerol degradation to butanol :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

glycolysis I (from glucose 6-phosphate) :
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

glycolysis II (from fructose 6-phosphate) :
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

glycolysis III (from glucose) :
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

glycolysis IV (plant cytosol) :
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

glycolysis V (Pyrococcus) :
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + 2 an oxidized ferredoxin + H2O ↔ 3-phospho-D-glycerate + 2 a reduced ferredoxin + 2 H+
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

glycolysis VI (metazoan) :
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

heterolactic fermentation :
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+

pentose phosphate pathway (non-oxidative branch) :
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate
D-sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate ↔ D-ribose 5-phosphate + D-xylulose 5-phosphate
D-glyceraldehyde 3-phosphate + D-sedoheptulose 7-phosphate ↔ β-D-fructofuranose 6-phosphate + D-erythrose 4-phosphate

pentose phosphate pathway (partial) :
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate
D-sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate ↔ D-ribose 5-phosphate + D-xylulose 5-phosphate

Rubisco shunt :
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate
D-sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate ↔ D-ribose 5-phosphate + D-xylulose 5-phosphate
D-glyceraldehyde 3-phosphate + D-sedoheptulose 7-phosphate ↔ β-D-fructofuranose 6-phosphate + D-erythrose 4-phosphate

sucrose biosynthesis I (from photosynthesis) :
fructose 1,6-bisphosphate ↔ dihydroxyacetone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+

sucrose degradation V (sucrose α-glucosidase) :
D-glyceraldehyde 3-phosphate ↔ dihydroxyacetone phosphate

superpathway of glucose and xylose degradation :
D-erythrose 4-phosphate + D-xylulose 5-phosphate ↔ β-D-fructofuranose 6-phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + NAD+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NADH + H+

Not in pathways:
β-D-fructofuranose 6-phosphate ↔ dihydroxyacetone + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate + NAD(P)+ + phosphate ↔ 1,3-bisphospho-D-glycerate + NAD(P)H + H+

In Reactions of unknown directionality:

Not in pathways:
sn-glycerol 3-phosphate + NADP+ = D-glyceraldehyde 3-phosphate + NADPH + H+
D-glyceraldehyde 3-phosphate + NAD(P)+ + H2O = 3-phospho-D-glycerate + NAD(P)H + 2 H+
D-ribose 5-phosphate + D-glyceraldehyde 3-phosphate + ammonium = pyridoxal 5'-phosphate + phosphate + H+ + 4 H2O
D-glyceraldehyde 3-phosphate + an oxidized ferredoxin = 3-phospho-D-glycerate + a reduced ferredoxin
D-glyceraldehyde 3-phosphate = D-ribulose 5-phosphate

In Transport reactions:
D-glyceraldehyde 3-phosphate[cytosol] + phosphate[extracellular space]D-glyceraldehyde 3-phosphate[cytosol] + phosphate[cytosol]

Enzymes inhibited by D-glyceraldehyde 3-phosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: glycerol-3-phosphate dehydrogenase, aerobic [Schryvers78] , 2-keto-3-deoxygluconate 6-phosphate aldolase

Inhibitor (Allosteric) of: glyceraldehyde-3-phosphate dehydrogenase [Tomschy93]

Inhibitor (Mechanism unknown) of: pyruvate formate-lyase [Takahashi82]

Credits:
Revised 28-Sep-2010 by Fulcher CA , SRI International


References

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

Schryvers78: Schryvers A, Lohmeier E, Weiner JH (1978). "Chemical and functional properties of the native and reconstituted forms of the membrane-bound, aerobic glycerol-3-phosphate dehydrogenase of Escherichia coli." J Biol Chem 253(3);783-8. PMID: 340460

Takahashi82: Takahashi S, Abbe K, Yamada T (1982). "Purification of pyruvate formate-lyase from Streptococcus mutans and its regulatory properties." J Bacteriol 149(3);1034-40. PMID: 7061379

Tomschy93: Tomschy A, Glockshuber R, Jaenicke R (1993). "Functional expression of D-glyceraldehyde-3-phosphate dehydrogenase from the hyperthermophilic eubacterium Thermotoga maritima in Escherichia coli. Authenticity and kinetic properties of the recombinant enzyme." Eur J Biochem 1993;214(1);43-50. PMID: 8508805


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 Tue Mar 3, 2015, biocyc11.