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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number96-26-4
WeightAverage: 90.0779
Monoisotopic: 90.031694058
Chemical FormulaC3H6O3
InChI KeyRXKJFZQQPQGTFL-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Glycerone or derivatives
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
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 substrateNon-inhibitor0.927
CYP450 2D6 substrateNon-inhibitor0.9599
CYP450 2C19 substrateNon-inhibitor0.8785
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point90 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraGC-MSMS/MS1D NMR2D NMR
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
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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

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