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MetaCyc Compound: glycerone phosphate

Abbrev Name: DHAP

Synonyms: DHAP, dihydroxyacetone phosphate, dihydroxyacetone-P, di-OH-acetone-P, dihydroxy-acetone phosphate, 3-hydroxy-2-oxopropyl phosphate

Chemical Formula: C3H5O6P

Molecular Weight: 168.04 Daltons

Monoisotopic Molecular Weight: 169.9980244673 Daltons

glycerone phosphate compound structure

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

InChI: InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)/p-2

InChIKey: InChIKey=GNGACRATGGDKBX-UHFFFAOYSA-L

Unification Links: CAS:57-04-5 , ChEBI:57642 , ChemSpider:3833110 , HMDB:HMDB01473 , IAF1260:33898 , KEGG:C00111 , MetaboLights:MTBLC57642 , PubChem:4643300

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -267.48264 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

CDP-archaeol biosynthesis :
sn-glycerol 1-phosphate + NAD(P)+glycerone phosphate + NAD(P)H + H+

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

grixazone biosynthesis :
2-amino-4,5-dihydroxy-6-oxo-7-(phosphonooxy)heptanoate ← L-aspartate-semialdehyde + glycerone phosphate

NAD biosynthesis I (from aspartate) , nicotine biosynthesis , superpathway of nicotine biosynthesis :
2-iminosuccinate + glycerone phosphate → quinolinate + phosphate + 2 H2O

superpathway of phosphatidate biosynthesis (yeast) :
glycerone phosphate + oleoyl-CoA → 1-oleoyl-2-lyso-glycerone phosphate + coenzyme A

Not in pathways:
glycerone phosphate → methylglyoxal + phosphate
L-aspartate + glycerone phosphate + oxygen → quinolinate + hydrogen peroxide + phosphate + H+ + 2 H2O

Reactions known to produce the compound:

autoinducer AI-2 degradation :
glycerone phosphate + acetyl-CoA ← 3-hydroxy-5-phosphonooxypentane-2,4-dione + coenzyme A

fluoroacetate and fluorothreonine biosynthesis :
5-fluoro-5-deoxy-D-ribulose 1-phosphate → fluoroacetaldehyde + glycerone phosphate

formaldehyde assimilation III (dihydroxyacetone cycle) , glycerol degradation II :
dihydroxyacetone + ATP → glycerone phosphate + ADP + H+

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 degradation V :
dihydroxyacetone + phosphoenolpyruvate → glycerone phosphate + pyruvate

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]

myo-inositol degradation I :
5-dehydro-2-deoxy-D-gluconate 6-phosphate → 3-oxopropanoate + glycerone phosphate

sucrose degradation V (sucrose α-glucosidase) :
β-D-fructofuranose 1-phosphate → glycerone phosphate + D-glyceraldehyde

sulfoglycolysis :
6-deoxy-6-sulfo-D-fructose 1-phosphate → sulfolactaldehyde + glycerone phosphate

Not in pathways:
sn-glycerol 3-phosphate + oxygen → hydrogen peroxide + glycerone phosphate
sn-glycerol 3-phosphate[in] + an electron-transfer quinone[membrane]glycerone phosphate[in] + an electron-transfer quinol[membrane]

Reactions known to both consume and produce the compound:

1,3-propanediol biosynthesis (engineered) :
sn-glycerol 3-phosphate + NAD+glycerone phosphate + NADH + H+
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate

Calvin-Benson-Bassham cycle :
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate
glycerone phosphate + D-erythrose 4-phosphate ↔ D-sedoheptulose-1,7-bisphosphate

D-arabinose degradation I :
D-ribulose 1-phosphate ↔ glycolaldehyde + glycerone phosphate

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 ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate

formaldehyde assimilation II (RuMP Cycle) , sucrose biosynthesis I (from photosynthesis) :
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate

formaldehyde assimilation III (dihydroxyacetone cycle) :
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate

fucose degradation , lactate biosynthesis (archaea) :
L-fuculose 1-phosphate ↔ (S)-lactaldehyde + glycerone phosphate

gluconeogenesis I :
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate

gluconeogenesis II (Methanobacterium thermoautotrophicum) :
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate

gluconeogenesis III :
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate

glycerol degradation to butanol , sucrose degradation V (sucrose α-glucosidase) :
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate

glycerol-3-phosphate shuttle , superpathway of phosphatidate biosynthesis (yeast) :
sn-glycerol 3-phosphate + NAD+glycerone phosphate + NADH + H+

glycolysis I (from glucose 6-phosphate) :
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate

glycolysis II (from fructose 6-phosphate) :
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate

glycolysis III (from glucose) :
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate

In Reactions of unknown directionality:

Not in pathways:
erythrulose 1-phosphate = formaldehyde + glycerone phosphate
a long-chain acyl-CoA + glycerone phosphate = an acylglycerone phosphate + coenzyme A

In Transport reactions:
a [PTS enzyme I]-Nπ-phospho-L-histidine + dihydroxyacetone[out]glycerone phosphate[in] + a [PTS enzyme I]-L-histidine

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

Enzymes activated by glycerone phosphate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: methylglyoxal synthase [Comment 1]

Enzymes inhibited by glycerone phosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: glycerol-3-phosphate dehydrogenase, aerobic [Schryvers78] , fructose-1,6-phosphate aldolase [Berthiaume89]

Inhibitor (Mechanism unknown) of: L-lactate dehydrogenase [Gordon76] , pyruvate formate-lyase [Takahashi82]

This compound has been characterized as an alternative substrate of the following enzymes: pyridoxal 5'-phosphate synthase complex , acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase , deoxyribose-phosphate aldolase


References

Berthiaume89: Berthiaume L, Beaudry D, Lazure C, Tolan DR, Sygusch J (1989). "Recombinant anaerobic maize aldolase: overexpression, characterization, and metabolic implications." Arch Biochem Biophys 272(2);281-9. PMID: 2751305

Gordon76: Gordon GL, Doelle HW (1976). "Purification, properties and immunological relationship of L (+)-lactate dehydrogenase from Lactobacillus casei." Eur J Biochem 67(2);543-55. PMID: 823016

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

Totemeyer98: Totemeyer S, Booth NA, Nichols WW, Dunbar B, Booth IR (1998). "From famine to feast: the role of methylglyoxal production in Escherichia coli." Mol Microbiol 1998;27(3);553-62. PMID: 9489667


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 Fri Sep 4, 2015, biocyc14.