Dihydroxyacetone
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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
- Weight
- Average: 90.0779
Monoisotopic: 90.031694058 - Chemical Formula
- C3H6O3
- Synonyms
- Dihydroxyacetone
- External IDs
- FEMA NO. 4033
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDihydroxyacetone kinase Not Available Citrobacter 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 outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- WITTGENSTEIN E, GUEST GM: Biochemical effects of dihydroxyacetone. J Invest Dermatol. 1961 Nov;37:421-6. [Article]
- 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]
- WITTGENSTEIN E, BERRY HK: Staining of skin with dihydroxyacetone. Science. 1960 Sep 30;132(3431):894-5. [Article]
- External Links
- Human Metabolome Database
- HMDB0001882
- KEGG Compound
- C00184
- PubChem Compound
- 670
- PubChem Substance
- 46505965
- ChemSpider
- 650
- 3430
- ChEBI
- 16016
- ChEMBL
- CHEMBL1229937
- ZINC
- ZINC000084397769
- PDBe Ligand
- 2HA
- Wikipedia
- Dihydroxyacetone
- PDB Entries
- 1ojr / 1un9 / 3ct4 / 3ohs / 3pnq / 6f2f
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 90 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 838.0 mg/mL ALOGPS logP -1.6 ALOGPS logP -1.5 Chemaxon logS 0.97 ALOGPS pKa (Strongest Acidic) 13.5 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 No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.974 Blood Brain Barrier + 0.6935 Caco-2 permeable - 0.728 P-glycoprotein substrate Non-substrate 0.7671 P-glycoprotein inhibitor I Non-inhibitor 0.9153 P-glycoprotein inhibitor II Non-inhibitor 0.867 Renal organic cation transporter Non-inhibitor 0.898 CYP450 2C9 substrate Non-substrate 0.8776 CYP450 2D6 substrate Non-substrate 0.8945 CYP450 3A4 substrate Non-substrate 0.7893 CYP450 1A2 substrate Non-inhibitor 0.8317 CYP450 2C9 inhibitor Non-inhibitor 0.927 CYP450 2D6 inhibitor Non-inhibitor 0.9599 CYP450 2C19 inhibitor Non-inhibitor 0.8785 CYP450 3A4 inhibitor Non-inhibitor 0.9576 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9198 Ames test AMES toxic 0.6611 Carcinogenicity Non-carcinogens 0.6087 Biodegradation Ready biodegradable 0.8559 Rat acute toxicity 1.4023 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9793 hERG inhibition (predictor II) Non-inhibitor 0.9456
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 109.5968215 predictedDarkChem Lite v0.1.0 [M-H]- 109.5482215 predictedDarkChem Lite v0.1.0 [M-H]- 124.771164 predictedDeepCCS 1.0 (2019) [M+H]+ 110.9553215 predictedDarkChem Lite v0.1.0 [M+H]+ 110.4107215 predictedDarkChem Lite v0.1.0 [M+H]+ 127.56859 predictedDeepCCS 1.0 (2019) [M+Na]+ 109.6338215 predictedDarkChem Lite v0.1.0 [M+Na]+ 109.6188215 predictedDarkChem Lite v0.1.0 [M+Na]+ 135.74623 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsDihydroxyacetone 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
Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51