Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000395
Identification
Name: Dihydroxyacetone phosphate
Description:Dihydroxyacetone phosphate is integral to the glycolysis metabolic pathway, and is one of the two products of breakdown of fructose 1,6-bisphosphate, along with glyceraldehyde 3-phosphate. It is rapidly and reversibly isomerised to glyceraldehyde 3-phosphate.
Structure
Thumb
Synonyms:
  • 1,3-Dihydroxy-2-Propanone mono(dihydrogen phosphate)
  • 1,3-Dihydroxy-2-propanone mono(dihydrogen phosphoric acid)
  • 1,3-Dihydroxy-2-propanone phosphate
  • 1,3-Dihydroxy-2-propanone phosphoric acid
  • 1,3-Dihydroxyacetone 1-phosphate
  • 1,3-Dihydroxyacetone 1-phosphoric acid
  • 1-Hydroxy-3-(phosphonooxy)-2-Propanone
  • 1-Hydroxy-3-(phosphonooxy)acetone
  • DHAP
  • Di-OH-acetone-P
  • Dihydroxy-acetone phosphate
  • Dihydroxy-acetone phosphoric acid
  • Dihydroxy-Acetone-P
  • Dihydroxy-acetone-phosphate
  • Dihydroxy-acetone-phosphoric acid
  • Dihydroxyacetone 3-phosphate
  • Dihydroxyacetone 3-phosphoric acid
  • Dihydroxyacetone monophosphate
  • Dihydroxyacetone monophosphoric acid
  • Dihydroxyacetone phosphate
  • Dihydroxyacetone phosphoric acid
  • Dihydroxyacetone-P
  • Dihydroxyacetone-phosphate
  • Dihydroxyacetone-phosphoric acid
  • Glycerone phosphate
  • Glycerone phosphoric acid
  • Glycerone-phosphate
  • Glycerone-phosphoric acid
  • Phosphate ester with 1,3-dihydroxy-2-propanone
  • Phosphorate ester with 1,3-dihydroxy-2-propanone
  • Phosphoric acid ester with 1,3-dihydroxy-2-propanone
Chemical Formula: C3H7O6P
Average Molecular Weight: 170.0578
Monoisotopic Molecular Weight: 169.998024468
InChI Key: GNGACRATGGDKBX-UHFFFAOYSA-N
InChI:InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
CAS number: 57-04-5
IUPAC Name:(3-hydroxy-2-oxopropoxy)phosphonic acid
Traditional IUPAC Name: dihydroxyacetone-phosphate
SMILES:OCC(=O)COP(O)(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbonyl compounds
Sub ClassKetones
Direct Parent Glycerone phosphates
Alternative Parents
Substituents
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility21.9 mg/mLALOGPS
logP-1.5ALOGPS
logP-1.7ChemAxon
logS-0.89ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.47 m3·mol-1ChemAxon
Polarizability12.64 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
L-Rhamnulose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde
Fructose 1-phosphate <> Dihydroxyacetone phosphate + D-Glyceraldehyde
D-Ribulose-1-phosphate <> Glycolaldehyde + Dihydroxyacetone phosphate
NAD(P)<sup>+</sup> + Glycerol 3-phosphate < NAD(P)H + Dihydroxyacetone phosphate + Hydrogen ion
Glycerol 3-phosphate + a ubiquinone <> Dihydroxyacetone phosphate + a ubiquinol
an electron-transfer-related quinone + Glycerol 3-phosphate <> an electron-transfer-related quinol + Dihydroxyacetone phosphate
Glycerol 3-phosphate + a quinone > Dihydroxyacetone phosphate + a quinol
Glycerol 3-phosphate + NAD(P)(+) > Dihydroxyacetone phosphate + NAD(P)H
Dihydroxyacetone phosphate > Pyruvaldehyde + Inorganic phosphate
Dihydroxyacetone phosphate + Iminoaspartic acid > Quinolinic acid +2 Water + Inorganic phosphate
Glycerol 3-phosphate + Quinone <> Dihydroxyacetone phosphate + Hydroquinone
Glycerol 3-phosphate + NAD + NADP <> Dihydroxyacetone phosphate + NADH + NADPH + Hydrogen ion
6-Deoxy-6-sulfo-D-fructose 1-phosphate <> Dihydroxyacetone phosphate + 2-Hydroxy-3-oxopropane-1-sulfonate
Fructose 1,6-bisphosphate + Fructose 1,6-bisphosphate <> D-Glyceraldehyde 3-phosphate + Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate
D-Glyceraldehyde 3-phosphate + D-Glyceraldehyde 3-phosphate <> Dihydroxyacetone phosphate
D-tagatofuranose 1,6-bisphosphate > Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate + D-Glyceraldehyde 3-phosphate
L-rhamnulose 1-phosphate + L-Rhamnulose 1-phosphate > Dihydroxyacetone phosphate + (S)-lactaldehyde + Lactaldehyde
L-fuculose 1-phosphate + L-Fuculose 1-phosphate > Dihydroxyacetone phosphate + (S)-lactaldehyde + Lactaldehyde
3-hydroxy-2,4-pentanedione 5-phosphate + Coenzyme A + 3-hydroxy-2,4-pentanedione 5-phosphate > Acetyl-CoA + Dihydroxyacetone phosphate
Dihydroxyacetone phosphate + Hydrogen ion + NADPH + NADPH > NADP + Glycerol 3-phosphate
Glycerol 3-phosphate + Ubiquinone-1 > Dihydroxyacetone phosphate + Ubiquinol-1
Glycerol 3-phosphate + menaquinone-8 > Menaquinol 8 + Dihydroxyacetone phosphate
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0uy4-3954100000-ab5b096e0eac9831cf42View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0g0m-3964100000-cd938c4cea382029ce88View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-7900000000-fec8dd084ee59efa2286View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9800000000-beb639c3fffc815897ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9000000000-580658c1ae323fa4f718View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-6900000000-4a0e75761c8eb8071d1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-7e5e1e00ef8f891ffe3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-08f155d8875692abc94bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-7900000000-fec8dd084ee59efa2286View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9800000000-beb639c3fffc815897ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9000000000-580658c1ae323fa4f718View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-6900000000-4a0e75761c8eb8071d1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-7e5e1e00ef8f891ffe3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-08f155d8875692abc94bView in MoNA
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
  • Roberts NB, Dutton J, Helliwell T, Rothwell PJ, Kavanagh JP: Pyrophosphate in synovial fluid and urine and its relationship to urinary risk factors for stone disease. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):529-34. Pubmed: 1332571
  • Schutgens RB, Wanders RJ, Heymans HS, Schram AW, Tager JM, Schrakamp G, van den Bosch H: Zellweger syndrome: biochemical procedures in diagnosis, prevention and treatment. J Inherit Metab Dis. 1987;10 Suppl 1:33-45. Pubmed: 3119940
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Yamamoto T, Moriwaki Y, Takahashi S, Ohata H, Nakano T, Yamakita J, Higashino K: Effect of glucagon on the xylitol-induced increase in the plasma concentration and urinary excretion of purine bases. Metabolism. 1996 Nov;45(11):1354-9. Pubmed: 8931639
Synthesis Reference: Ballou, Clinton E.; Fischer, Hermann O. L. The synthesis of dihydroxyacetone phosphate. Journal of the American Chemical Society (1956), 78 1659-61.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15835
HMDB IDHMDB01473
Pubchem Compound ID668
Kegg IDC00111
ChemSpider ID648
WikipediaDihydroxyacetone phosphate
BioCyc IDDIHYDROXY-ACETONE-PHOSPHATE
EcoCyc IDDIHYDROXY-ACETONE-PHOSPHATE
Ligand Expo13P