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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:37 UTC
HMDB IDHMDB01473
Secondary Accession Numbers
  • HMDB11735
Metabolite Identification
Common NameDihydroxyacetone phosphate
DescriptionDihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.
Structure
Thumb
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 FormulaC3H7O6P
Average Molecular Weight170.0578
Monoisotopic Molecular Weight169.998024468
IUPAC Name(3-hydroxy-2-oxopropoxy)phosphonic acid
Traditional IUPAC Name3-hydroxy-2-oxopropoxyphosphonic acid
CAS Registry Number57-04-5
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 KeyGNGACRATGGDKBX-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganophosphorus Compounds
ClassOrganic Phosphoric Acids and Derivatives
Sub ClassOrganophosphate Esters
Other Descriptors
  • Aliphatic Acyclic Compounds
  • glycerone phosphates(ChEBI)
Substituents
  • Alpha Ketoaldehyde
  • Ketone
  • Organic Hypophosphite
  • Organic Phosphite
  • Primary Alcohol
Direct ParentOrganophosphate Esters
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
  • Component of Glycerophospholipid metabolism
  • Component of Inositol metabolism
ApplicationNot Available
Cellular locations
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility21.9 g/LALOGPS
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 area104.06ChemAxon
rotatable bond count4ChemAxon
refractivity30.47ChemAxon
polarizability12.64ChemAxon
Spectra
SpectraGC-MS
Biological Properties
Cellular Locations
  • Peroxisome
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064map00051
GluconeogenesisSMP00128map00010
Glycerol Phosphate ShuttleSMP00124Not Available
Glycerolipid MetabolismSMP00039map00561
GlycolysisSMP00040map00010
Mitochondrial Electron Transport ChainSMP00355map00190
Phospholipid BiosynthesisSMP00025map00564
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified12.1 +/- 5.1 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified15.6 +/- 4.56 uMAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified140 (60-220) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.88 +/- 0.34 uMAdult (>18 years old)BothTransaldolase deficiency details
Associated Disorders and Diseases
Disease References
Transaldolase deficiency
  1. 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
Associated OMIM IDs
DrugBank IDDB04326
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001618
KNApSAcK IDC00007560
Chemspider ID648
KEGG Compound IDC00111
BioCyc IDDIHYDROXY-ACETONE-PHOSPHATE
BiGG ID33898
Wikipedia LinkDihydroxyacetone phosphate
NuGOwiki LinkHMDB01473
Metagene LinkHMDB01473
METLIN ID6262
PubChem Compound668
PDB ID13P
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 References
  1. 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
  2. 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
  3. 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
  4. 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

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPP
Uniprot ID:
P05187
Molecular weight:
57953.31
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPI
Uniprot ID:
P09923
Molecular weight:
56811.695
General function:
Involved in catalytic activity
Specific function:
This isozyme may play a role in skeletal mineralization.
Gene Name:
ALPL
Uniprot ID:
P05186
Molecular weight:
57304.435
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
General function:
Involved in calcium ion binding
Specific function:
Not Available
Gene Name:
GPD2
Uniprot ID:
P43304
Molecular weight:
80851.99
Reactions
Glycerol 3-phosphate + a quinone → Dihydroxyacetone phosphate + a quinoldetails
Glycerol 3-phosphate + FAD → Dihydroxyacetone phosphate + FADHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
GPD1
Uniprot ID:
P21695
Molecular weight:
37567.4
Reactions
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADHdetails
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADH + Hydrogen Iondetails
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Plays a key role in glycolysis and gluconeogenesis. In addition, may also function as scaffolding protein (By similarity).
Gene Name:
ALDOA
Uniprot ID:
P04075
Molecular weight:
39419.675
Reactions
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
beta-D-Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
Sedoheptulose 1,7-bisphosphate → Dihydroxyacetone phosphate + D-Erythrose 4-phosphatedetails
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Not Available
Gene Name:
ALDOC
Uniprot ID:
P09972
Molecular weight:
39455.505
Reactions
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
beta-D-Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
Sedoheptulose 1,7-bisphosphate → Dihydroxyacetone phosphate + D-Erythrose 4-phosphatedetails
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
P05062
Molecular weight:
39472.715
Reactions
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
beta-D-Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphatedetails
Sedoheptulose 1,7-bisphosphate → Dihydroxyacetone phosphate + D-Erythrose 4-phosphatedetails
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
GNPAT
Uniprot ID:
O15228
Molecular weight:
77187.185
Reactions
Acyl-CoA + Dihydroxyacetone phosphate → Coenzyme A + acylglycerone phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
TPI1
Uniprot ID:
P60174
Molecular weight:
26669.33
Reactions
D-Glyceraldehyde 3-phosphate → Dihydroxyacetone phosphatedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
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.
Gene Name:
DAK
Uniprot ID:
Q3LXA3
Molecular weight:
58946.49
Reactions
Adenosine triphosphate + Dihydroxyacetone → ADP + Dihydroxyacetone phosphatedetails
General function:
Involved in oxidoreductase activity
Specific function:
Plays a role in regulating cardiac sodium current; decreased enzymatic activity with resulting increased levels of glycerol 3-phosphate activating the DPD1L-dependent SCN5A phosphorylation pathway, may ultimately lead to decreased sodium current; cardiac sodium current may also be reduced due to alterations of NAD(H) balance induced by DPD1L.
Gene Name:
GPD1L
Uniprot ID:
Q8N335
Molecular weight:
38418.44
Reactions
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADHdetails
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADH + Hydrogen Iondetails
General function:
Involved in catalytic activity
Specific function:
D-glyceraldehyde 3-phosphate = glycerone phosphate
Gene Name:
Not Available
Uniprot ID:
Q2QD09
Molecular weight:
26942.6