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Identification
NameDihydroxyacetone
Accession NumberDB01775  (EXPT00122)
Typesmall molecule
Groupsexperimental
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
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number96-26-4
WeightAverage: 90.0779
Monoisotopic: 90.031694058
Chemical FormulaC3H6O3
InChI KeyInChIKey=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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassMonosaccharides
Direct parentTrioses
Alternative parentsKetones; Primary Alcohols; Polyamines; Enolates; Aldehydes
Substituentsketone; enolate; primary alcohol; polyamine; alcohol; carbonyl group; aldehyde
Classification descriptionThis compound belongs to the trioses. These are monosaccharides whose carbohydrate unit contains three carbon atoms.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.927
CYP450 2D6 substrate Non-inhibitor 0.9599
CYP450 2C19 substrate Non-inhibitor 0.8785
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point90 °CPhysProp
Predicted Properties
PropertyValueSource
water solubility8.38e+02 g/lALOGPS
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 area57.53ChemAxon
rotatable bond count2ChemAxon
refractivity19.6ChemAxon
polarizability8.1ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis Reference

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

US4076589
General Reference
  1. WITTGENSTEIN E, GUEST GM: Biochemical effects of dihydroxyacetone. J Invest Dermatol. 1961 Nov;37:421-6. Pubmed
  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
  3. WITTGENSTEIN E, BERRY HK: Staining of skin with dihydroxyacetone. Science. 1960 Sep 30;132:894-5. Pubmed
External Links
ResourceLink
KEGG CompoundC00184
PubChem Compound670
PubChem Substance46505965
ChemSpider650
ChEBI16016
ChEMBL
HET2HA
WikipediaDihydroxyacetone
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Dihydroxyacetone kinase

Kind: protein

Organism: Citrobacter freundii

Pharmacological action: unknown

Components

Name UniProt ID Details
Dihydroxyacetone kinase P45510 Details

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
  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

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15