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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:45:01 UTC
HMDB IDHMDB0001473
Secondary Accession Numbers
  • HMDB0011735
  • HMDB01473
  • HMDB11735
Metabolite Identification
Common NameDihydroxyacetone phosphate
DescriptionDihydroxyacetone phosphate, also known as dihydroxy-acetone-p or 3-phosphate, dihydroxyacetone, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate, which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Dihydroxyacetone phosphate is a drug. Dihydroxyacetone phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydroxyacetone phosphate exists in all living species, ranging from bacteria to humans. Within humans, dihydroxyacetone phosphate participates in a number of enzymatic reactions. In particular, ubiquinol 8 and dihydroxyacetone phosphate can be biosynthesized from coenzyme Q10 and glycerol 3-phosphate; which is mediated by the enzyme glycerol-3-phosphate dehydrogenase, mitochondrial. In addition, dihydroxyacetone phosphate can be converted into glycerol 3-phosphate; which is mediated by the enzyme glycerol-3-phosphate dehydrogenase [nad(+)], cytoplasmic. In humans, dihydroxyacetone phosphate is involved in the metabolic disorder called the mitochondrial electron transport chain pathway. Outside of the human body, dihydroxyacetone phosphate has been detected, but not quantified in, several different foods, such as alaska wild rhubarbs, coconuts, black walnuts, hazelnuts, and java plums. This could make dihydroxyacetone phosphate a potential biomarker for the consumption of these foods. Dihydroxyacetone phosphate is a potentially toxic compound. Dihydroxyacetone phosphate has been found to be associated with several diseases such as lewy body disease, alzheimer's disease, and frontotemporal dementia; also dihydroxyacetone phosphate has been linked to the inborn metabolic disorders including transaldolase deficiency. It is rapidly and reversibly isomerised to glyceraldehyde 3-phosphate. Click on genes, proteins and metabolites below to link to respective articles. Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is the anion with the formula HOCH2C(O)CH2OPO32-. Compound C00111 at KEGG Pathway Database.
Structure
Data?1563860701
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 Name(3-hydroxy-2-oxopropoxy)phosphonic acid
Traditional Namedihydroxyacetone-phosphate
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
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Area104.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.47 m³·mol⁻¹ChemAxon
Polarizability12.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0uy4-3954100000-ab5b096e0eac9831cf42JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0g0m-3964100000-cd938c4cea382029ce88JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uy4-3954100000-ab5b096e0eac9831cf42JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0g0m-3964100000-cd938c4cea382029ce88JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-9400000000-a02e9df63512a60b9324JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9200000000-79dfc0ac375f4d056dc9JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kb-9600000000-050f206e1fed5aaa8c1fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9100000000-c7eb3c008e10f8e15386JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-0f8d50d1d029df4e6c43JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-7c2d8125a273e3fae4f6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-517dcdb0a35f00b4b491JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9000000000-b8d3aeb9415528f3d035JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-7900000000-fec8dd084ee59efa2286JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9800000000-beb639c3fffc815897ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9000000000-580658c1ae323fa4f718JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-6900000000-4a0e75761c8eb8071d1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-7e5e1e00ef8f891ffe3eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-08f155d8875692abc94bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-7900000000-fec8dd084ee59efa2286JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9800000000-beb639c3fffc815897ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9000000000-580658c1ae323fa4f718JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-6900000000-4a0e75761c8eb8071d1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-7e5e1e00ef8f891ffe3eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-08f155d8875692abc94bJSpectraViewer
Biological Properties
Cellular Locations
  • Peroxisome
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
SalivaDetected and Quantified10.33 +/- 5.13 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified1.87 +/- 0.809 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified2.08 +/- 1.62 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified3.00 +/- 1.57 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified3.68 +/- 1.39 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.88 +/- 0.34 uMAdult (>18 years old)BothTransaldolase deficiency details
SalivaDetected and Quantified8.45 +/- 4.68 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified10.80 +/- 9.74 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified8.71 +/- 3.88 uMAdult (>18 years old)BothLewy body disease 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 ]
Alzheimer's disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Associated OMIM IDs
DrugBank IDDB04326
Phenol Explorer Compound IDNot Available
FoodDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
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. 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 ]
  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 ]
  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 ]
  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;2:18. [PubMed:15882454 ]

Only showing the first 10 proteins. There are 14 proteins in total.

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 + Glyceraldehyde 3-phosphatedetails
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + Glyceraldehyde 3-phosphatedetails
Sedoheptulose 1,7-bisphosphate → Dihydroxyacetone phosphate + D-Erythrose 4-phosphatedetails
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
Dihydroxyacetone phosphate + D-Erythrose 4-phosphate → Sedoheptulose 1,7-bisphosphatedetails
Dihydroxyacetone phosphate + Glyceraldehyde 3-phosphate → Fructose 1,6-bisphosphatedetails
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 + Glyceraldehyde 3-phosphatedetails
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + 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 + Glyceraldehyde 3-phosphatedetails
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + 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

Only showing the first 10 proteins. There are 14 proteins in total.