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Dihydroxyacetone (YMDB00018)

Identification
YMDB IDYMDB00018
NameDihydroxyacetone
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDihydroxyacetone, also known as DHA or glycerone, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Dihydroxyacetone is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydroxyacetone exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1,3 Dihydroxy 2 propanone
  • 1,3-Dihydroxy-2-propanone
  • 1,3-Dihydroxyacetone
  • 1,3-Dihydroxydimethyl ketone
  • 1,3-Dihydroxypropan-2-one
  • 1,3-Dihydroxypropanone
  • 1,3-Propanediol-2-one
  • a,a'-Dihydroxyacetone
  • a,Alpha'-dihydroxyacetone
  • Aliphatic ketone
  • alpha,Alpha'-dihydroxyacetone
  • Bis(hydroxymethyl) ketone
  • Chromelin
  • DHA
  • dihydroxy-acetone
  • Dihydroxyacetone
  • Dihyxal
  • glycerone
  • ICN brand OF dihydroxyacetone
  • Ketochromin
  • Otan
  • Oxantin
  • Oxatone
  • Protosol
  • Soleal
  • Summers brand OF dihydroxyacetone
  • Triulose
  • Vitadye
  • Viticolor
  • α,alpha'-dihydroxyacetone
CAS number96-26-4
WeightAverage: 90.0779
Monoisotopic: 90.031694058
InChI KeyRXKJFZQQPQGTFL-UHFFFAOYSA-N
InChIInChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2
IUPAC Name1,3-dihydroxypropan-2-one
Traditional IUPAC Namedihydroxyacetone
Chemical FormulaC3H6O3
SMILES[H]OC([H])([H])C(=O)C([H])([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Glycerone or derivatives
  • Monosaccharide
  • 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 point90 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility838 g/LALOGPS
logP-1.6ALOGPS
logP-1.5ChemAxon
logS0.97ALOGPS
pKa (Strongest Acidic)13.49ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.6 m³·mol⁻¹ChemAxon
Polarizability8.1 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
MintyFDB030826
SMPDB Pathways
Glycerol metabolismPW002407 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerolipid metabolismec00561 Map00561
Methane metabolismec00680 Map00680
SMPDB Reactions
Dihydroxyacetone + NADPH + hydron → NADP + Glycerol
Dihydroxyacetone + Adenosine triphosphate → Glycerone phosphate + ADP
KEGG Reactions
Dihydroxyacetone + Adenosine triphosphate → Dihydroxyacetone phosphate + hydron + ADP
NADP + Glycerol → Dihydroxyacetone + NADPH + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0w2j-1900000000-b3783d91181e1657545dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0wa0-5900000000-f95dddc55209203877e3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gvk-1900000000-bd875a5207eb70c5beb8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0w2j-1900000000-b3783d91181e1657545dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0wa0-5900000000-f95dddc55209203877e3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0w2j-2900000000-f84cc49dd11822409addJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9000000000-089abb74f439c9265bb6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9320000000-6bdc226e79d3bc473a66JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-0e836f7fe0512bb62662JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059i-9000000000-d1a13699d0d0cbea36b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-57da9a85ff22593c3ab3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-55ab07d1079db56cca4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9000000000-f9afe28f3ce4c2f913d5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-8e71e2b93a16e2be3db1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-7bb646a5cb5ca825e7b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fu-9000000000-ab60a50ef2013d762751JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-ef7c943cff3a9adfd1edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-9000000000-3deebe0c487d3443c844JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9000000000-73f63f3caf2a9bf8b899JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-195717f89ffa991dcb57JSpectraViewer
1D NMR1H 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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D 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
  • Molin, M., Norbeck, J., Blomberg, A. (2003). "Dihydroxyacetone kinases in Saccharomyces cerevisiae are involved in detoxification of dihydroxyacetone." J Biol Chem 278:1415-1423.12401799
  • Costenoble, R., Valadi, H., Gustafsson, L., Niklasson, C., Franzen, C. J. (2000). "Microaerobic glycerol formation in Saccharomyces cerevisiae." Yeast 16:1483-1495.11113971
Synthesis Reference:Hochuli, Erich; Taylor, Keith E.; Dutler, Hans. Dihydroxyacetone reductase from Mucor javanicus. 2. Identification of the physiological substrate and reactivity towards related compounds. European Journal of Biochemistry (1977), 75(2), 433-9.
External Links:
ResourceLink
CHEBI ID16016
HMDB IDHMDB01882
Pubchem Compound ID670
Kegg IDC00184
ChemSpider ID650
FOODB IDFDB030826
WikipediaDihydroxyacetone
BioCyc ID1-ACYL-GLYCERONE-3-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. Protein GCY
General function:
Involved in oxidoreductase activity
Specific function:
Unknown function which seems to be not essential
Gene Name:
GCY1
Uniprot ID:
P14065
Molecular weight:
35078.89844
Reactions