Dihydroxyacetone

Identification

Name
Dihydroxyacetone
Accession Number
DB01775  (EXPT00122)
Type
Small Molecule
Groups
Experimental
Description

A ketotriose compound. Its addition to blood preservation solutions results in better maintenance of 2,3-diphosphoglycerate levels during storage. It is readily phosphorylated to dihydroxyacetone phosphate by triokinase in erythrocytes. In combination with naphthoquinones it acts as a sunscreening agent. [PubChem]

Structure
Thumb
Synonyms
Not Available
External IDs
FEMA NO. 4033
Categories
UNII
O10DDW6JOO
CAS number
96-26-4
Weight
Average: 90.0779
Monoisotopic: 90.031694058
Chemical Formula
C3H6O3
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
SMILES
OCC(=O)CO

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydroxyacetone kinaseNot AvailableCitrobacter freundii
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Glycerol MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

William Charney, "Process for the production of dihydroxyacetone." U.S. Patent US4076589, issued February 28, 1978.

US4076589
General References
  1. WITTGENSTEIN E, GUEST GM: Biochemical effects of dihydroxyacetone. J Invest Dermatol. 1961 Nov;37:421-6. [PubMed:14007781]
  2. GOLDMAN L, WITTGENSTEIN E, BLANEY D, GOLDMAN J, SAWYER F: Studies of some physical properties of the dihydroxyacetone color complex. J Invest Dermatol. 1961 Apr;36:233-4. [PubMed:13706567]
  3. WITTGENSTEIN E, BERRY HK: Staining of skin with dihydroxyacetone. Science. 1960 Sep 30;132(3431):894-5. [PubMed:13845496]
External Links
Human Metabolome Database
HMDB0001882
KEGG Compound
C00184
PubChem Compound
670
PubChem Substance
46505965
ChemSpider
650
ChEBI
16016
ChEMBL
CHEMBL1229937
HET
2HA
Wikipedia
Dihydroxyacetone
PDB Entries
1ojr / 1un9 / 3ct4 / 3ohs / 3pnq / 6f2f

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)90 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility838.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.6 m3·mol-1ChemAxon
Polarizability8.1 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.974
Blood Brain Barrier+0.6935
Caco-2 permeable-0.728
P-glycoprotein substrateNon-substrate0.7671
P-glycoprotein inhibitor INon-inhibitor0.9153
P-glycoprotein inhibitor IINon-inhibitor0.867
Renal organic cation transporterNon-inhibitor0.898
CYP450 2C9 substrateNon-substrate0.8776
CYP450 2D6 substrateNon-substrate0.8945
CYP450 3A4 substrateNon-substrate0.7893
CYP450 1A2 substrateNon-inhibitor0.8317
CYP450 2C9 inhibitorNon-inhibitor0.927
CYP450 2D6 inhibitorNon-inhibitor0.9599
CYP450 2C19 inhibitorNon-inhibitor0.8785
CYP450 3A4 inhibitorNon-inhibitor0.9576
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9198
Ames testAMES toxic0.6611
CarcinogenicityNon-carcinogens0.6087
BiodegradationReady biodegradable0.8559
Rat acute toxicity1.4023 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9793
hERG inhibition (predictor II)Non-inhibitor0.9456
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0w2j-1900000000-b3783d91181e1657545d
GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)GC-MSsplash10-0wa0-5900000000-f95dddc55209203877e3
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0gvk-1900000000-bd875a5207eb70c5beb8
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0w2j-1900000000-b3783d91181e1657545d
GC-MS Spectrum - GC-MSGC-MSsplash10-0wa0-5900000000-f95dddc55209203877e3
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0w2j-2900000000-f84cc49dd11822409add
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-7bb646a5cb5ca825e7b5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fu-9000000000-ab60a50ef2013d762751
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-ef7c943cff3a9adfd1ed
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-0e836f7fe0512bb62662
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-059i-9000000000-d1a13699d0d0cbea36b5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-57da9a85ff22593c3ab3
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as monosaccharides. These 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
Glycerone and derivatives / Alpha-hydroxy ketones / Primary alcohols / Organic oxides / Hydrocarbon derivatives
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)

Targets

Kind
Protein
Organism
Citrobacter freundii
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the phosphorylation of dihydroxyacetone.
Gene Name
dhaK
Uniprot ID
P45510
Uniprot Name
Dihydroxyacetone kinase
Molecular Weight
57939.515 Da
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]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:09