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Record Information
Version1.0
Creation Date2016-09-30 22:46:27 UTC
Update Date2020-05-21 16:29:07 UTC
BMDB IDBMDB0001473
Secondary Accession Numbers
  • BMDB01473
Metabolite Identification
Common NameDihydroxyacetone phosphate
DescriptionDihydroxyacetone phosphate, also known as Dihydroxyacetone phosphate or Dihydroxyacetone phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Dihydroxyacetone phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydroxyacetone phosphate exists in all living species, ranging from bacteria to humans. Dihydroxyacetone phosphate participates in a number of enzymatic reactions, within cattle. In particular, Ubiquinol 8 and dihydroxyacetone phosphate can be biosynthesized from coenzyme Q10 and glycerol 3-phosphate through the action of the enzyme glycerol-3-phosphate dehydrogenase, mitochondrial. In addition, Dihydroxyacetone phosphate can be converted into glycerol 3-phosphate through its interaction with the enzyme glycerol-3-phosphate dehydrogenase [nad(+)], cytoplasmic. In cattle, dihydroxyacetone phosphate is involved in the metabolic pathway called the mitochondrial electron transport chain pathway. Dihydroxyacetone phosphate is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
1,3-Dihydroxy-2-propanone monodihydrogen phosphateChEBI
1,3-Dihydroxy-2-propanone phosphateChEBI
1,3-Dihydroxyacetone 1-phosphateChEBI
1-Hydroxy-3-(phosphonooxy)-2-propanoneChEBI
1-Hydroxy-3-(phosphonooxy)acetoneChEBI
3-Hydroxy-2-oxopropyl phosphateChEBI
DHAPChEBI
Dihydroxyacetone monophosphateChEBI
Glycerone monophosphateChEBI
Glycerone phosphateChEBI
1,3-Dihydroxy-2-propanone monodihydrogen phosphoric acidGenerator
1,3-Dihydroxy-2-propanone phosphoric acidGenerator
1,3-Dihydroxyacetone 1-phosphoric acidGenerator
3-Hydroxy-2-oxopropyl phosphoric acidGenerator
Dihydroxyacetone monophosphoric acidGenerator
Glycerone monophosphoric acidGenerator
Glycerone phosphoric acidGenerator
Dihydroxyacetone phosphoric acidGenerator
1,3-Dihydroxy-2-propanone mono(dihydrogen phosphate)HMDB
Di-OH-acetone-pHMDB
Dihydroxy-acetone-pHMDB
Dihydroxy-acetone-phosphateHMDB
Dihydroxyacetone 3-phosphateHMDB
Dihydroxyacetone-pHMDB
Dihydroxyacetone-phosphateHMDB
Glycerone-phosphateHMDB
Phosphoric acid ester with 1,3-dihydroxy-2-propanoneHMDB
3-Phosphate, dihydroxyacetoneHMDB
Phosphate, dihydroxyacetoneHMDB
Dihydroxyacetone 3 phosphateHMDB
Chemical FormulaC3H7O6P
Average Molecular Weight170.0578
Monoisotopic Molecular Weight169.998024468
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number57-04-5
SMILESNot Available
InChI Identifier
InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
InChI KeyGNGACRATGGDKBX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001473
DrugBank IDDB04326
Phenol Explorer Compound IDNot Available
FooDB IDFDB001618
KNApSAcK IDC00007560
Chemspider ID648
KEGG Compound IDC00111
BioCyc IDDIHYDROXY-ACETONE-PHOSPHATE
BiGG ID33898
Wikipedia LinkDihydroxyacetone_phosphate
METLIN ID6262
PubChem Compound668
PDB IDNot Available
ChEBI ID16108
References
Synthesis ReferenceBallou, 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
General ReferencesNot Available

Enzymes

General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
GPD2
Uniprot ID:
A6QLU1
Molecular weight:
80763.0
Reactions
Glycerol 3-phosphate + Quinone → Dihydroxyacetone phosphate + Hydroquinonedetails
Dihydroxyacetone phosphate + Quinone → Glycerol 3-phosphate + Hydroquinonedetails
Coenzyme Q10 + Glycerol 3-phosphate → Ubiquinol + Dihydroxyacetone phosphatedetails
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
GNPAT
Uniprot ID:
A4IF87
Molecular weight:
77664.0
Reactions
Eicosanoyl-CoA + Dihydroxyacetone phosphate → DHAP(18:0) + Coenzyme Adetails
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes both the phosphorylation of dihydroxyacetone and of glyceraldehyde, and the splitting of ribonucleoside diphosphate-X compounds among which FAD is the best substrate. Represses IFIH1-mediated cellular antiviral response.
Gene Name:
TKFC
Uniprot ID:
Q58DK4
Molecular weight:
59124.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOA
Uniprot ID:
A6QLL8
Molecular weight:
39436.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOC
Uniprot ID:
Q3ZBY4
Molecular weight:
39382.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
A5PK73
Molecular weight:
39527.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
Q3T0S5
Molecular weight:
39543.0
Reactions
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Triosephosphate isomerase is an extremely efficient metabolic enzyme that catalyzes the interconversion between dihydroxyacetone phosphate (DHAP) and D-glyceraldehyde-3-phosphate (G3P) in glycolysis and gluconeogenesis.
Gene Name:
TPI1
Uniprot ID:
Q5E956
Molecular weight:
26690.0
Reactions
Dihydroxyacetone phosphate → D-Glyceraldehyde 3-phosphatedetails
General function:
Energy production and conversion
Specific function:
Catalyzes the oxidation of D-2-hydroxyglutarate to alpha-ketoglutarate.
Gene Name:
D2HGDH
Uniprot ID:
Q1JPD3
Molecular weight:
59056.0
Reactions
Eicosanoyl-CoA + Dihydroxyacetone phosphate → DHAP(18:0) + Coenzyme Adetails
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
GPD1
Uniprot ID:
Q5EA88
Molecular weight:
37648.0
Reactions
Dihydroxyacetone phosphate + NADH → Glycerol 3-phosphate + NADdetails
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADHdetails