NAV

Dihydroxyacetone

Identification

Generic Name
Dihydroxyacetone
DrugBank Accession Number
DB01775
Background

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]

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 90.0779
Monoisotopic: 90.031694058
Chemical Formula
C3H6O3
Synonyms
  • Dihydroxyacetone
External IDs
  • FEMA NO. 4033
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aliphatic acyclic compound / Alpha-hydroxy ketone / Carbonyl group / Glycerone or derivatives / Hydrocarbon derivative / Ketone / Monosaccharide / Organic oxide / Primary alcohol
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
ketotriose (CHEBI:16016) / Ketoses (C00184) / a small molecule (DIHYDROXYACETONE)
Affected organisms
Not Available

Chemical Identifiers

UNII
O10DDW6JOO
CAS number
96-26-4
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

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. [Article]
  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. [Article]
  3. WITTGENSTEIN E, BERRY HK: Staining of skin with dihydroxyacetone. Science. 1960 Sep 30;132(3431):894-5. [Article]
Human Metabolome Database
HMDB0001882
KEGG Compound
C00184
PubChem Compound
670
PubChem Substance
46505965
ChemSpider
650
RxNav
3430
ChEBI
16016
ChEMBL
CHEMBL1229937
ZINC
ZINC000084397769
PDBe Ligand
2HA
Wikipedia
Dihydroxyacetone
PDB Entries
1ojr / 1un9 / 3ct4 / 3ohs / 3pnq / 6f2f

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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)13.5Chemaxon
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-MSsplash10-0a59-9000000000-089abb74f439c9265bb6
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/MSsplash10-00dl-9000000000-f2aa37b7d031c5c592fd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-0e814246202bc945fa23
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-9000000000-67dea3f1d3ca88b8ec74
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-81022651e058a9ae9eb7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-9e2bab7e30574fd7ec65
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9000000000-02be3f57e566066b67e8
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-109.5968215
predicted
DarkChem Lite v0.1.0
[M-H]-109.5482215
predicted
DarkChem Lite v0.1.0
[M-H]-124.771164
predicted
DeepCCS 1.0 (2019)
[M+H]+110.9553215
predicted
DarkChem Lite v0.1.0
[M+H]+110.4107215
predicted
DarkChem Lite v0.1.0
[M+H]+127.56859
predicted
DeepCCS 1.0 (2019)
[M+Na]+109.6338215
predicted
DarkChem Lite v0.1.0
[M+Na]+109.6188215
predicted
DarkChem Lite v0.1.0
[M+Na]+135.74623
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Dihydroxyacetone kinase
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51