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Record Information
Version3.6
Creation Date2006-02-28 09:34:34 UTC
Update Date2016-05-13 20:31:15 UTC
HMDB IDHMDB01882
Secondary Accession NumbersNone
Metabolite Identification
Common NameDihydroxyacetone
DescriptionDihydroxyacetone is 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; Dihydroxyacetone (also known as DHA) is a triose carbohydrate with chemical formula C3H6O3. It is the simplest of all ketoses and, having no chiral centre, is the only one that has no optical activity. -- Wikipedia; Dihydroxyacetone is a simple non-toxic sugar. It is often derived from plant sources such as sugar beets and sugar cane, by the fermentation of glycerin; it is a white crystalline powder which is water soluble. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
ChromelinKegg
1,3-DihydroxyacetoneKegg
1,3-Dihydroxy-2-propanoneKegg
1,3-Dihydroxypropan-2-oneKegg
1,3-Dihydroxydimethyl ketoneHMDB
1,3-DihydroxypropanoneHMDB
a,A'-dihydroxyacetoneHMDB
Aliphatic ketoneHMDB
Bis(hydroxymethyl) ketoneHMDB
Dihydroxy-acetoneHMDB
DihyxalHMDB
GlyceroneHMDB
KetochrominHMDB
OtanHMDB
OxantinHMDB
OxatoneHMDB
ProtosolHMDB
SolealHMDB
TriuloseHMDB
ViticolorHMDB
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 KeyInChIKey=RXKJFZQQPQGTFL-UHFFFAOYSA-N
Chemical 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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
  • Component of Glycerolipid metabolism
  • Component of Glycerophospholipid metabolism
  • Component of Inositol metabolism
  • Energy source
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point90 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0w2j-1900000000-b3783d91181e1657545dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0wa0-5900000000-f95dddc55209203877e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-7bb646a5cb5ca825e7b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fu-9000000000-ab60a50ef2013d762751View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-ef7c943cff3a9adfd1edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-0e836f7fe0512bb62662View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059i-9000000000-d1a13699d0d0cbea36b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-57da9a85ff22593c3ab3View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location
  • Muscle
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified6.807 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified>0.65 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.07 (0.02-0.18) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.10 (0.05-0.16) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01775
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB009294
KNApSAcK IDNot Available
Chemspider ID650
KEGG Compound IDC00184
BioCyc IDDIHYDROXYACETONE
BiGG ID34170
Wikipedia LinkDihydroxyacetone
NuGOwiki LinkHMDB01882
Metagene LinkHMDB01882
METLIN ID6368
PubChem Compound670
PDB ID2HA
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)Download (PDF)
General References
  1. Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [6321058 ]
  2. Phillipou G, Seaborn CJ, Phillips PJ: Re-evaluation of the fructosamine reaction. Clin Chem. 1988 Aug;34(8):1561-4. [3402055 ]
  3. Blake SM, Treble NJ: Popliteus tendon tenosynovitis. Br J Sports Med. 2005 Dec;39(12):e42; discussion e42. [16306488 ]
  4. Forest SE, Grothaus JT, Ertel KD, Rader C, Plante J: Fluorescence spectral imaging of dihydroxyacetone on skin in vivo. Photochem Photobiol. 2003 May;77(5):524-30. [12812295 ]
  5. Taylor CR, Kwangsukstith C, Wimberly J, Kollias N, Anderson RR: Turbo-PUVA: dihydroxyacetone-enhanced photochemotherapy for psoriasis: a pilot study. Arch Dermatol. 1999 May;135(5):540-4. [10328194 ]
  6. Kerr HH, Pantely GA, Metcalfe J, Welch JE: Reduction of human blood O2 affinity using dihydroxyacetone, phosphate, and pyruvate. J Appl Physiol. 1979 Sep;47(3):478-81. [118143 ]
  7. 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. [13706567 ]
  8. WITTGENSTEIN E, BERRY HK: Staining of skin with dihydroxyacetone. Science. 1960 Sep 30;132(3431):894-5. [13845496 ]
  9. WITTGENSTEIN E, GUEST GM: Biochemical effects of dihydroxyacetone. J Invest Dermatol. 1961 Nov;37:421-6. [14007781 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPP
Uniprot ID:
P05187
Molecular weight:
57953.31
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPI
Uniprot ID:
P09923
Molecular weight:
56811.695
General function:
Involved in catalytic activity
Specific function:
This isozyme may play a role in skeletal mineralization.
Gene Name:
ALPL
Uniprot ID:
P05186
Molecular weight:
57304.435
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes both the phosphorylation of dihydroxyacetone and of glyceraldehyde, and the splitting of ribonucleoside diphosphate-X compounds among which FAD is the best substrate.
Gene Name:
DAK
Uniprot ID:
Q3LXA3
Molecular weight:
58946.49
Reactions
Adenosine triphosphate + Dihydroxyacetone → ADP + Dihydroxyacetone phosphatedetails