Human Metabolome Database Version 3.5

Showing metabocard for Dihydroxyacetone phosphate (HMDB01473)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:37 -0700
HMDB ID HMDB01473
Secondary Accession Numbers
  • HMDB11735
Metabolite Identification
Common Name Dihydroxyacetone phosphate
Description Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,3-Dihydroxy-2-Propanone mono(dihydrogen phosphate)
  2. 1,3-Dihydroxy-2-propanone phosphate
  3. 1,3-Dihydroxyacetone 1-phosphate
  4. 1-Hydroxy-3-(phosphonooxy)-2-Propanone
  5. 1-Hydroxy-3-(phosphonooxy)acetone
  6. DHAP
  7. Di-OH-acetone-P
  8. Dihydroxy-Acetone-P
  9. Dihydroxy-acetone-phosphate
  10. Dihydroxyacetone 3-phosphate
  11. Dihydroxyacetone monophosphate
  12. Dihydroxyacetone phosphate
  13. Dihydroxyacetone-P
  14. Dihydroxyacetone-phosphate
  15. Glycerone phosphate
  16. Glycerone-phosphate
  17. Phosphoric acid ester with 1,3-dihydroxy-2-propanone
Chemical Formula C3H7O6P
Average Molecular Weight 170.0578
Monoisotopic Molecular Weight 169.998024468
IUPAC Name (3-hydroxy-2-oxopropoxy)phosphonic acid
Traditional IUPAC Name 3-hydroxy-2-oxopropoxyphosphonic acid
CAS Registry Number 57-04-5
SMILES OCC(=O)COP(O)(O)=O
InChI Identifier InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
InChI Key GNGACRATGGDKBX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organophosphorus Compounds
Class Organic Phosphoric Acids and Derivatives
Sub Class Organophosphate Esters
Other Descriptors
  • Aliphatic Acyclic Compounds
  • glycerone phosphates(ChEBI)
Substituents
  • Alpha Ketoaldehyde
  • Ketone
  • Organic Hypophosphite
  • Organic Phosphite
  • Primary Alcohol
Direct Parent Organophosphate Esters
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
  • Component of Glycerophospholipid metabolism
  • Component of Inositol metabolism
Application Not Available
Cellular locations
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 21.9 g/L ALOGPS
LogP -1.49 ALOGPS
LogP -1.7 ChemAxon
LogS -0.89 ALOGPS
pKa (strongest acidic) 1.19 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 104.06 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 30.47 ChemAxon
Polarizability 12.64 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations
  • Peroxisome
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Fructose and Mannose Degradation SMP00064 map00051 Link_out
Glycerol Phosphate Shuttle SMP00124 Not Available
Mitochondrial Electron Transport Chain SMP00355 map00190 Link_out
Phospholipid Biosynthesis SMP00025 map00564 Link_out
Glycerolipid Metabolism SMP00039 map00561 Link_out
Glycolysis SMP00040 map00010 Link_out
Gluconeogenesis SMP00128 map00010 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
12.1 +/- 5.1 uM Newborn (0-30 days old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
15.6 +/- 4.56 uM Adult (>18 years old) Both Normal
Cellular Cytoplasm Detected and Quantified
140 (60-220) uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 1.88 +/- 0.34 uM Adult (>18 years old) Both Transaldolase deficiency
Associated Disorders and Diseases
Disease References
Transaldolase deficiency
  • Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. Pubmed: 12881455 Link_out
      Associated OMIM IDs
      • 606003 Link_out (Transaldolase deficiency)
      DrugBank ID DB04326 Link_out
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB001618
      KNApSAcK ID C00007560 Link_out
      Chemspider ID 648 Link_out
      KEGG Compound ID C00111 Link_out
      BioCyc ID DIHYDROXY-ACETONE-PHOSPHATE Link_out
      BiGG ID 33898 Link_out
      Wikipedia Link Dihydroxyacetone phosphate Link_out
      NuGOwiki Link HMDB01473 Link_out
      Metagene Link HMDB01473 Link_out
      METLIN ID 6262 Link_out
      PubChem Compound 668 Link_out
      PDB ID 13P Link_out
      ChEBI ID 16108 Link_out
      References
      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
      General References
      1. 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 Link_out
      2. 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 Link_out
      3. 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 Link_out
      4. 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 Link_out

      Enzymes
      Name: Alkaline phosphatase, placental type
      Reactions: Not Available
      Gene Name: ALPP
      Uniprot ID: P05187 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Intestinal-type alkaline phosphatase
      Reactions: Not Available
      Gene Name: ALPI
      Uniprot ID: P09923 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alkaline phosphatase, tissue-nonspecific isozyme
      Reactions: Not Available
      Gene Name: ALPL
      Uniprot ID: P05186 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alkaline phosphatase, placental-like
      Reactions: Not Available
      Gene Name: ALPPL2
      Uniprot ID: P10696 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Glycerol-3-phosphate dehydrogenase, mitochondrial
      Reactions:
      Glycerol 3-phosphate + a quinone unknown Dihydroxyacetone phosphate + a quinol details
      Glycerol 3-phosphate + FAD unknown Dihydroxyacetone phosphate + FADH details
      Gene Name: GPD2
      Uniprot ID: P43304 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic
      Reactions:
      Glycerol 3-phosphate + NAD unknown Dihydroxyacetone phosphate + NADH details
      Glycerol 3-phosphate + NAD unknown Dihydroxyacetone phosphate + NADH + Hydrogen Ion details
      Gene Name: GPD1
      Uniprot ID: P21695 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Fructose-bisphosphate aldolase A
      Reactions:
      Fructose 1,6-bisphosphate unknown Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate details
      beta-D-Fructose 1,6-bisphosphate unknown Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate details
      Sedoheptulose 1,7-bisphosphate unknown Dihydroxyacetone phosphate + D-Erythrose 4-phosphate details
      Fructose 1-phosphate unknown Dihydroxyacetone phosphate + Glyceraldehyde details
      Gene Name: ALDOA
      Uniprot ID: P04075 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Fructose-bisphosphate aldolase C
      Reactions:
      Fructose 1,6-bisphosphate unknown Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate details
      beta-D-Fructose 1,6-bisphosphate unknown Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate details
      Sedoheptulose 1,7-bisphosphate unknown Dihydroxyacetone phosphate + D-Erythrose 4-phosphate details
      Fructose 1-phosphate unknown Dihydroxyacetone phosphate + Glyceraldehyde details
      Gene Name: ALDOC
      Uniprot ID: P09972 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Fructose-bisphosphate aldolase B
      Reactions:
      Fructose 1,6-bisphosphate unknown Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate details
      beta-D-Fructose 1,6-bisphosphate unknown Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate details
      Sedoheptulose 1,7-bisphosphate unknown Dihydroxyacetone phosphate + D-Erythrose 4-phosphate details
      Fructose 1-phosphate unknown Dihydroxyacetone phosphate + Glyceraldehyde details
      Gene Name: ALDOB
      Uniprot ID: P05062 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Dihydroxyacetone phosphate acyltransferase
      Reactions:
      Acyl-CoA + Dihydroxyacetone phosphate unknown Coenzyme A + acylglycerone phosphate details
      Gene Name: GNPAT
      Uniprot ID: O15228 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Triosephosphate isomerase
      Reactions:
      D-Glyceraldehyde 3-phosphate unknown Dihydroxyacetone phosphate details
      Gene Name: TPI1
      Uniprot ID: P60174 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)
      Reactions:
      Adenosine triphosphate + Dihydroxyacetone unknown ADP + Dihydroxyacetone phosphate details
      Gene Name: DAK
      Uniprot ID: Q3LXA3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Glycerol-3-phosphate dehydrogenase 1-like protein
      Reactions:
      Glycerol 3-phosphate + NAD unknown Dihydroxyacetone phosphate + NADH details
      Glycerol 3-phosphate + NAD unknown Dihydroxyacetone phosphate + NADH + Hydrogen Ion details
      Gene Name: GPD1L
      Uniprot ID: Q8N335 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Triosephosphate isomerase
      Reactions: Not Available
      Gene Name: Not Available
      Uniprot ID: Q2QD09 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA