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Dihydroxyacetone (ECMDB01882) (M2MDB000427)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:54:55 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:12 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Dihydroxyacetone | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Dihydroxyacetone or DHA, also known as glycerone, is a simple carbohydrate (a triose) with formula C3H6O3. It is an intermedate in the process of glycerolipid metabolism. It is converted from glycerol by glycerol dehydrogenase, NAD (EC:1.1.1.6) and converts to glycerone phosphate by dihydroxyacetone kinase (EC:2.7.1.-). (KEGG) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C3H6O3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 90.0779 Monoisotopic: 90.031694058 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | RXKJFZQQPQGTFL-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 96-26-4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 1,3-dihydroxypropan-2-one | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | dihydroxyacetone | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OCC(=O)CO | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Monosaccharides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 90 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Fructose 6-phosphate <> Dihydroxyacetone + D-Glyceraldehyde 3-phosphate Dihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid Glycerol + NAD <> Dihydroxyacetone + Hydrogen ion + NADH Adenosine triphosphate + Dihydroxyacetone <> ADP + Dihydroxyacetone phosphate Dihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid Fructose 6-phosphate > Dihydroxyacetone + D-Glyceraldehyde 3-phosphate Glycerol + NAD > Dihydroxyacetone + NADH | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in transferase activity, transferring phosphorus-containing groups
- Specific function:
- General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
- Gene Name:
- ptsI
- Uniprot ID:
- P08839
- Molecular weight:
- 63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes the NAD-dependent oxidation of glycerol to dihydroxyacetone (glycerone). Allows microorganisms to utilize glycerol as a source of carbon under anaerobic conditions. In E.coli, an important role of gldA is also likely to regulate the intracellular level of dihydroxyacetone by catalyzing the reverse reaction, i.e. the conversion of dihydroxyacetone into glycerol. Possesses a broad substrate specificity, since it is also able to oxidize 1,2-propanediol and to reduce glycolaldehyde, methylglyoxal and hydroxyacetone into ethylene glycol, lactaldehyde and 1,2-propanediol, respectively
- Gene Name:
- gldA
- Uniprot ID:
- P0A9S5
- Molecular weight:
- 38712
Reactions
Glycerol + NAD(+) = glycerone + NADH. |
- General function:
- Involved in glycerone kinase activity
- Specific function:
- Dihydroxyacetone binding subunit of the dihydroxyacetone kinase, which is responsible for phosphorylating dihydroxyacetone. Binds covalently dihydroxyacetone in hemiaminal linkage. Acts also as a corepressor of dhaR by binding to its sensor domain, in the absence of dihydroxyacetone
- Gene Name:
- dhaK
- Uniprot ID:
- P76015
- Molecular weight:
- 38215
- General function:
- Involved in catalytic activity
- Specific function:
- D-fructose 6-phosphate = glycerone + D- glyceraldehyde 3-phosphate
- Gene Name:
- fsaB
- Uniprot ID:
- P32669
- Molecular weight:
- 23555
Reactions
D-fructose 6-phosphate = glycerone + D-glyceraldehyde 3-phosphate. |
- General function:
- Involved in glycerone kinase activity
- Specific function:
- ADP-binding subunit of the dihydroxyacetone kinase, which is responsible for phosphorylating dihydroxyacetone. DhaL- ADP receives a phosphoryl group from dhaM and transmits it to dihydroxyacetone. DhaL-ADP acts also as a coactivator by binding to the sensor domain of dhaR. DhaL-ATP is inactive
- Gene Name:
- dhaL
- Uniprot ID:
- P76014
- Molecular weight:
- 22632
- General function:
- Involved in catalytic activity
- Specific function:
- D-fructose 6-phosphate = glycerone + D- glyceraldehyde 3-phosphate
- Gene Name:
- fsaA
- Uniprot ID:
- P78055
- Molecular weight:
- 22997
Reactions
D-fructose 6-phosphate = glycerone + D-glyceraldehyde 3-phosphate. |
- General function:
- Involved in transferase activity, transferring phosphorus-containing groups
- Specific function:
- Phosphotransferase subunit of the dihydroxyacetone kinase, which is responsible for phosphorylating dihydroxyacetone. DhaM serves as the phosphoryl donor. It is phosphorylated by HPr, then it donates its phosphoryl group to dhaL-ADP, which eventually transmits it to dihydroxyacetone
- Gene Name:
- dhaM
- Uniprot ID:
- P37349
- Molecular weight:
- 51448
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine. |
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine. |
Protein EIIA N(pi)-phospho-L-histidine + dhaL-ADP = protein EIIA + dhaL-ATP. |
- General function:
- Involved in sugar:hydrogen symporter activity
- Specific function:
- General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
- Gene Name:
- ptsH
- Uniprot ID:
- P0AA04
- Molecular weight:
- 9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine. |
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368