Dihydroxyacetone (YMDB00018)

Identification

YMDB ID

YMDB00018

Name

Dihydroxyacetone

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Dihydroxyacetone, 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

MOL SDF PDB SMILES InChI

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 number

96-26-4

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

IUPAC Name

1,3-dihydroxypropan-2-one

Traditional IUPAC Name

dihydroxyacetone

Chemical Formula

C₃H₆O₃

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharides

Alternative Parents

Substituents

Glycerone or derivatives
Monosaccharide
Alpha-hydroxy ketone
Ketone
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ketotriose (CHEBI:16016 )
Ketoses (C00184 )
a small molecule (DIHYDROXYACETONE )

Physical Properties

State

Solid

Charge

Melting point

90 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	838 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.5	ChemAxon
logS	0.97	ALOGPS
pKa (Strongest Acidic)	13.49	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	19.6 m³·mol⁻¹	ChemAxon
Polarizability	8.1 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Minty	FDB030826

SMPDB Pathways

Glycerol metabolism

PW002407

KEGG Pathways

Glycerolipid metabolism	ec00561
Methane metabolism	ec00680

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 Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0w2j-1900000000-b3783d91181e1657545d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-0wa0-5900000000-f95dddc55209203877e3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0gvk-1900000000-bd875a5207eb70c5beb8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0w2j-1900000000-b3783d91181e1657545d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0wa0-5900000000-f95dddc55209203877e3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0w2j-2900000000-f84cc49dd11822409add	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9000000000-089abb74f439c9265bb6	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-9320000000-6bdc226e79d3bc473a66	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-0e836f7fe0512bb62662	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-059i-9000000000-d1a13699d0d0cbea36b5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-57da9a85ff22593c3ab3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-55ab07d1079db56cca4c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-9000000000-f9afe28f3ce4c2f913d5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-8e71e2b93a16e2be3db1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-7bb646a5cb5ca825e7b5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fu-9000000000-ab60a50ef2013d762751	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-ef7c943cff3a9adfd1ed	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9000000000-3deebe0c487d3443c844	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9000000000-73f63f3caf2a9bf8b899	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-195717f89ffa991dcb57	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	16016
HMDB ID	HMDB01882
Pubchem Compound ID	670
Kegg ID	C00184
ChemSpider ID	650
FOODB ID	FDB030826
Wikipedia	Dihydroxyacetone
BioCyc ID	1-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

Structure for #<Compound:0x044e6c3c>

Enzymes

Reactions

Reactions

Reactions