glycerone phosphate (PAMDB110137)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110137
Identification
Name: glycerone phosphate
Description:A dianionic form of glycerone phosphate arising from deprotonation of the phosphate OH groups; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • DHAP
  • dihydroxyacetone phosphate
  • dihydroxyacetone-P
  • di-OH-acetone-P
  • dihydroxy-acetone phosphate
  • 3-hydroxy-2-oxopropyl phosphate
Chemical Formula: C3H5O6P
Average Molecular Weight: 168.04
Monoisotopic Molecular Weight: 169.9980244673
InChI Key: GNGACRATGGDKBX-UHFFFAOYSA-L
InChI: InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)/p-2
CAS number: 57-04-5
IUPAC Name:3-hydroxy-2-oxopropyl phosphate
Traditional IUPAC Name: dihydroxyacetone-phosphate
SMILES:C(C(=O)CO)OP([O-])([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic oxygen compounds
Sub ClassOrganooxygen compounds
Direct Parent Monosaccharide phosphates
Alternative Parents
Substituents
  • Glycerone phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Glycerone or derivatives
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Alpha-hydroxy ketone
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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: Not Available
Reactions:
β-D-fructofuranose 1-phosphate → glycerone phosphate + D-glyceraldehyde
glycerone phosphate + Hydrogen ion → sn-glycerol 3-phosphate
ETR-Quinones + sn-glycerol 3-phosphate → ETR-Quinols + glycerone phosphate
sn-glycerol 3-phosphate + NAD+ → glycerone phosphate + NADH + Hydrogen ion
glycerone phosphate + oleoyl-CoA → 1-oleoyl-2-lyso-glycerone phosphate + coenzyme A
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
Predicted GC-MSPredicted GC-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:
  • 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. [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. [1332571 ]
  • 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. [8931639 ]
  • 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. [3119940 ]
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
CAS57-04-5
ChEBI57642
ChemSpider3833110
HMDBHMDB01473
IAF126033898
KEGGC00111
MetaboLightsMTBLC57642
PubChem4643300