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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-26 03:48:08 UTC
HMDB IDHMDB0001473
Secondary Accession Numbers
  • HMDB01473
  • HMDB11735
StatusDetected and Quantified
Metabolite Identification
Common NameDihydroxyacetone phosphate
DescriptionDihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.
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
1,3-Dihydroxy-2-propanone monodihydrogen phosphoric acidGenerator
Dihydroxyacetone 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
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
Glycerone-phosphateHMDB
Phosphoric acid ester with 1,3-dihydroxy-2-propanoneHMDB
3-Phosphate, dihydroxyacetoneMeSH
Phosphate, dihydroxyacetoneMeSH
Dihydroxyacetone 3 phosphateMeSH
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
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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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
Process
Naturally occurring process:
Biological process:
Biochemical pathway:
Disposition
Biological Location:
Source:
Biofluid and excreta:
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 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
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
GC-MSGC-MS Spectrum - GC-MSsplash10-0uy4-3954100000-ab5b096e0eac9831cf42View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0g0m-3964100000-cd938c4cea382029ce88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kb-9600000000-050f206e1fed5aaa8c1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9100000000-c7eb3c008e10f8e15386View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-0f8d50d1d029df4e6c43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-7c2d8125a273e3fae4f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-517dcdb0a35f00b4b491View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9000000000-b8d3aeb9415528f3d035View 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
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
Biological Properties
Cellular Locations
  • Peroxisome
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Saliva
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
D-glyceric aciduraPw000505Pw000505 greyscalePw000505 simpleNot Available
Familial lipoprotein lipase deficiencyPw000506Pw000506 greyscalePw000506 simpleNot Available
Fanconi-bickel syndromePw000548Pw000548 greyscalePw000548 simpleNot Available
Fructose and Mannose DegradationPw000025Pw000025 greyscalePw000025 simpleMap00051
Fructose intolerance, hereditaryPw000702Pw000702 greyscalePw000702 simpleNot Available
Displaying entries 1 - 5 of 27 in total
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
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
BiofluidStatusValueAgeSexConditionReferenceDetails
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 ]
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 LinkHMDB0001473
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;2:18. [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
Dihydroxyacetone phosphate + D-Erythrose 4-phosphate → Sedoheptulose 1,7-bisphosphatedetails
Dihydroxyacetone phosphate + D-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 + 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