Dihydroxyacetone phosphate (YMDB00322)

Identification
YMDB IDYMDB00322
NameDihydroxyacetone phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDihydroxyacetone phosphate (DHAP) is an important intermediate in lipid biosynthesis and in glycolysis. Dihydroxyacetone phosphate is one of the two products of breakdown of fructose 1,6-bisphosphate, along with glyceraldehyde 3-phosphate. It is rapidly and reversibly isomerised to glyceraldehyde 3-phosphate. 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. [Wikipedia]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-hydroxy-3-(phosphonooxy)-2-Propanone
  • 1-Hydroxy-3-(phosphonooxy)acetone
  • 1,3-dihydroxy-2-Propanone mono(dihydrogen phosphate)
  • 1,3-Dihydroxy-2-propanone phosphate
  • 1,3-Dihydroxyacetone 1-phosphate
  • DHAP
  • di-OH-acetone-P
  • Dihydroxy-Acetone-P
  • dihydroxy-acetone-phosphate
  • dihydroxyacetone 3-phosphate
  • Dihydroxyacetone monophosphate
  • Dihydroxyacetone phosphate
  • Dihydroxyacetone phosphic acid
  • dihydroxyacetone-P
  • dihydroxyacetone-phosphate
  • Glycerone phosphate
  • glycerone-phosphate
  • Phosphoric acid ester with 1,3-dihydroxy-2-propanone
  • 1,3-Dihydroxy-2-propanone monodihydrogen phosphate
  • 3-Hydroxy-2-oxopropyl phosphate
  • Glycerone monophosphate
  • 1,3-Dihydroxy-2-propanone monodihydrogen phosphoric acid
  • 1,3-Dihydroxy-2-propanone phosphoric acid
  • 1,3-Dihydroxyacetone 1-phosphoric acid
  • 3-Hydroxy-2-oxopropyl phosphoric acid
  • Dihydroxyacetone monophosphoric acid
  • Glycerone monophosphoric acid
  • Glycerone phosphoric acid
  • Dihydroxyacetone phosphoric acid
  • 3-Phosphate, dihydroxyacetone
  • Phosphate, dihydroxyacetone
  • Dihydroxyacetone 3 phosphate
CAS number57-04-5
WeightAverage: 170.0578
Monoisotopic: 169.998024468
InChI KeyGNGACRATGGDKBX-UHFFFAOYSA-N
InChIInChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
IUPAC Name(3-hydroxy-2-oxopropoxy)phosphonic acid
Traditional IUPAC Namedihydroxyacetone-phosphate
Chemical FormulaC3H7O6P
SMILES[H]OC([H])([H])C(=O)C([H])([H])OP(=O)(O[H])O[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Biological Properties
Cellular Locations
  • mitochondrion
  • lipid particle
  • endoplasmic reticulum
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Cardiolipin Biosynthesis CL(10:0/10:0/14:0/30:0)PW003514 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/14:1(11Z)/26:0)PW003515 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/14:1(11Z)/26:1(11Z))PW003516 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/14:1(11Z)/26:1(9Z))PW003517 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/14:1(11Z)/28:0)PW003518 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fructose and mannose metabolismec00051 Map00051
Galactose metabolismec00052 Map00052
Glycerolipid metabolismec00561 Map00561
Glycerophospholipid metabolismec00564 Map00564
Glycolysis / Gluconeogenesisec00010 Map00010
SMPDB Reactions
Fructose 1,6-bisphosphate → D-Glyceraldehyde 3-phosphate + Dihydroxyacetone phosphate
Dihydroxyacetone phosphate ↔ D-Glyceraldehyde 3-phosphate
KEGG Reactions
D-fructose 1-phosphate ↔ D-glyceraldehyde + Dihydroxyacetone phosphate
Dihydroxyacetone + Adenosine triphosphate → Dihydroxyacetone phosphate + hydron + ADP
Fructose 1,6-bisphosphate ↔ D-Glyceraldehyde 3-phosphate + Dihydroxyacetone phosphate
Glycerol 3-phosphate + FAD → FADH2 + Dihydroxyacetone phosphate
NADH + Dihydroxyacetone phosphate + hydron → NAD + Glycerol 3-phosphate
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
330 ± 10 µM Synthetic medium with 2% glucoseaerobic;growing cellsBaker's yeastPMID: 6229402
120 ± 10 µM Synthetic medium with 2% glucoseaerobic;resting cellsBaker's yeastPMID: 6229402
460 ± 70 µM Synthetic medium with 2% galactoseaerobic;resting cellsBaker's yeastPMID: 6229402
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0udi-2900000000-6091e72aad27af4c7971JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-00fr-0900000000-b948afb7a993bfbaf1dfJSpectraViewer | 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9100000000-83b3c3bba9003d67c444JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fdk-9800000000-dad61e875fa6524224d8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007k-9200000000-3ce8b7e1264e4e13f792JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Thevelein, J. M., Hohmann, S. (1995). "Trehalose synthase: guard to the gate of glycolysis in yeast?" Trends Biochem Sci 20:3-10.7878741
  • Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
  • Athenstaedt, K., Weys, S., Paltauf, F., Daum, G. (1999). "Redundant systems of phosphatidic acid biosynthesis via acylation of glycerol-3-phosphate or dihydroxyacetone phosphate in the yeast Saccharomyces cerevisiae." J Bacteriol 181:1458-1463.10049376
  • Boles, E., Zimmermann, F. K. (1993). "Saccharomyces cerevisiae phosphoglucose isomerase and fructose bisphosphate aldolase can be replaced functionally by the corresponding enzymes of Escherichia coli and Drosophila melanogaster." Curr Genet 23:187-191.8435847
  • Zheng, Z., Zou, J. (2001). "The initial step of the glycerolipid pathway: identification of glycerol 3-phosphate/dihydroxyacetone phosphate dual substrate acyltransferases in Saccharomyces cerevisiae." J Biol Chem 276:41710-41716.11544256
  • Albertyn, J., Hohmann, S., Thevelein, J. M., Prior, B. A. (1994). "GPD1, which encodes glycerol-3-phosphate dehydrogenase, is essential for growth under osmotic stress in Saccharomyces cerevisiae, and its expression is regulated by the high-osmolarity glycerol response pathway." Mol Cell Biol 14:4135-4144.8196651
  • Inoue, Y., Watanabe, K., Shimosaka, M., Saikusa, T., Fukuda, Y., Murata, K., Kimura, A. (1985). "Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae." Eur J Biochem 153:243-247.3908097
  • Lagunas, R., Gancedo, C. (1983). "Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae." Eur J Biochem 137:479-483.6229402
Synthesis Reference:Ballou, Clinton E.; Fischer, Hermann O. L. The synthesis of dihydroxyacetone phosphate. Journal of the American Chemical Society (1956), 78 1659-61.
External Links:
ResourceLink
CHEBI ID16108
HMDB IDHMDB01473
Pubchem Compound ID668
Kegg IDC00111
ChemSpider ID648
FOODB IDFDB001618
WikipediaDihydroxyacetone_phosphate
BioCyc IDDIHYDROXY-ACETONE-PHOSPHATE

Enzymes

Protein Details
1. Dihydroxyacetone kinase 2
General function:
Involved in glycerone kinase activity
Specific function:
ATP + glycerone = ADP + glycerone phosphate
Gene Name:
DAK2
Uniprot ID:
P43550
Molecular weight:
62134.0
Reactions
ATP + glycerone → ADP + glycerone phosphate.
Protein Details
2. Dihydroxyacetone kinase 1
General function:
Involved in glycerone kinase activity
Specific function:
ATP + glycerone = ADP + glycerone phosphate
Gene Name:
DAK1
Uniprot ID:
P54838
Molecular weight:
62206.10156
Reactions
ATP + glycerone → ADP + glycerone phosphate.
Protein Details
3. Glycerol-3-phosphate O-acyltransferase 1
General function:
Involved in acyltransferase activity
Specific function:
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase
Gene Name:
GPT1
Uniprot ID:
P32784
Molecular weight:
85693.5
Reactions
Acyl-CoA + sn-glycerol 3-phosphate → CoA + 1-acyl-sn-glycerol 3-phosphate.
Acyl-CoA + glycerone phosphate → CoA + acylglycerone phosphate.
Protein Details
4. Glycerol-3-phosphate O-acyltransferase 2
General function:
Involved in acyltransferase activity
Specific function:
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase
Gene Name:
GPT2
Uniprot ID:
P36148
Molecular weight:
83644.0
Reactions
Acyl-CoA + sn-glycerol 3-phosphate → CoA + 1-acyl-sn-glycerol 3-phosphate.
Acyl-CoA + glycerone phosphate → CoA + acylglycerone phosphate.
Protein Details
5. Glycerol-3-phosphate dehydrogenase [NAD+] 1
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the production and accumulation of glycerol during hyperosmotic stress conditions. Glycerol acts as a osmoregulator that prevents loss of water and turgor of the cells
Gene Name:
GPD1
Uniprot ID:
Q00055
Molecular weight:
42868.5
Reactions
sn-glycerol 3-phosphate + NAD(+) → glycerone phosphate + NADH.
Protein Details
6. Glycerol-3-phosphate dehydrogenase [NAD+] 2, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the production of glycerol under anaerobic growth conditions. Glycerol production serves as a redox sink by consuming the excess cytosolic NADH during anaerobic metabolism
Gene Name:
GPD2
Uniprot ID:
P41911
Molecular weight:
49421.30078
Reactions
sn-glycerol 3-phosphate + NAD(+) → glycerone phosphate + NADH.
Protein Details
7. Glycerol-3-phosphate dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
sn-glycerol 3-phosphate + a quinone = glycerone phosphate + a quinol
Gene Name:
GUT2
Uniprot ID:
P32191
Molecular weight:
72388.29688
Reactions
sn-glycerol 3-phosphate + a quinone → glycerone phosphate + a quinol.
Protein Details
8. Fructose-bisphosphate aldolase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the aldol condensation of dihydroxyacetone phosphate (DHAP or glycerone-phosphate) with glyceraldehyde 3- phosphate (G3P) to form fructose 1,6-bisphosphate (FBP) in gluconeogenesis and the reverse reaction in glycolysis
Gene Name:
FBA1
Uniprot ID:
P14540
Molecular weight:
39620.5
Reactions
D-fructose 1,6-bisphosphate → glycerone phosphate + D-glyceraldehyde 3-phosphate.
Protein Details
9. Triosephosphate isomerase
General function:
Involved in catalytic activity
Specific function:
D-glyceraldehyde 3-phosphate = glycerone phosphate
Gene Name:
TPI1
Uniprot ID:
P00942
Molecular weight:
26795.30078
Reactions
D-glyceraldehyde 3-phosphate → glycerone phosphate.