Showing metabocard for Dihydroxyacetone (BMDB0001882)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:48:35 UTC
Update Date2020-06-04 20:47:46 UTC
BMDB IDBMDB0001882
Secondary Accession Numbers
  • BMDB01882
Metabolite Identification
Common NameDihydroxyacetone
DescriptionDihydroxyacetone, also known as chromelin or DHA, belongs to the class of organic compounds known as monosaccharides. Monosaccharides 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. Dihydroxyacetone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Dihydroxyacetone exists in all living species, ranging from bacteria to humans. In cattle, dihydroxyacetone is involved in the metabolic pathway called the mitochondrial electron transport chain pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3-Dihydroxy-2-propanoneChEBI
1,3-DihydroxyacetoneChEBI
1,3-Dihydroxydimethyl ketoneChEBI
1,3-Dihydroxypropan-2-oneChEBI
1,3-DihydroxypropanoneChEBI
1,3-Propanediol-2-oneChEBI
alpha,Alpha'-dihydroxyacetoneChEBI
Bis(hydroxymethyl) ketoneChEBI
DHAChEBI
GlyceroneChEBI
ChromelinKegg
a,Alpha'-dihydroxyacetoneGenerator
Α,alpha'-dihydroxyacetoneGenerator
a,A'-dihydroxyacetoneHMDB
Aliphatic ketoneHMDB
Dihydroxy-acetoneHMDB
DihyxalHMDB
KetochrominHMDB
OtanHMDB
OxantinHMDB
OxatoneHMDB
ProtosolHMDB
SolealHMDB
TriuloseHMDB
ViticolorHMDB
1,3 Dihydroxy 2 propanoneHMDB
Summers brand OF dihydroxyacetoneHMDB
ICN brand OF dihydroxyacetoneHMDB
VitadyeHMDB
Chemical FormulaC3H6O3
Average Molecular Weight90.0779
Monoisotopic Molecular Weight90.031694058
IUPAC Name1,3-dihydroxypropan-2-one
Traditional Namedihydroxyacetone
CAS Registry Number96-26-4
SMILES
OCC(=O)CO
InChI Identifier
InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2
InChI KeyRXKJFZQQPQGTFL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides 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 ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Glycerone or derivatives
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point90 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.6 m³·mol⁻¹ChemAxon
Polarizability8.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Epidermis
  • Liver
  • Milk
  • Ruminal Fluid
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified16.56 +/- 4.22 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified6.5 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified6.8 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified6.3 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified16.6 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified7.2 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified7.9 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified6.4 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified15.6 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified7 +/- 2 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified7 +/- 3 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified7 +/- 2 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified17 +/- 5 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Ruminal FluidDetected and Quantified6.32 +/- 1.46 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
 details
HMDB IDHMDB0001882
DrugBank IDDB01775
Phenol Explorer Compound IDNot Available
FooDB IDFDB030826
KNApSAcK IDNot Available
Chemspider ID650
KEGG Compound IDC00184
BioCyc IDDIHYDROXYACETONE
BiGG ID34170
Wikipedia LinkDihydroxyacetone
METLIN ID6368
PubChem Compound670
PDB IDNot Available
ChEBI ID16016
References
Synthesis ReferenceHochuli, Erich; Taylor, Keith E.; Dutler, Hans. Dihydroxyacetone reductase from Mucor javanicus. 2. Identification of the physiological substrate and reactivity towards related compounds. European Journal of Biochemistry (1977), 75(2), 433-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]