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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-02-28 09:34:34 UTC
Update Date2019-07-23 05:45:09 UTC
HMDB IDHMDB0001882
Secondary Accession Numbers
  • HMDB01882
Metabolite Identification
Common NameDihydroxyacetone
DescriptionDihydroxyacetone (also known as DHA) 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. Dihydroxyacetone is the simplest of all ketoses and, having no chiral centre, is the only one that has no optical activity. 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. Dihydroxyacetone is a white crystalline powder which is water soluble (Wikipedia).
Structure
Data?1563860709
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

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 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 Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.6 m³·mol⁻¹ChemAxon
Polarizability8.1 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0w2j-1900000000-b3783d91181e1657545dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0wa0-5900000000-f95dddc55209203877e3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gvk-1900000000-bd875a5207eb70c5beb8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0w2j-1900000000-b3783d91181e1657545dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0wa0-5900000000-f95dddc55209203877e3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0w2j-2900000000-f84cc49dd11822409addJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9000000000-089abb74f439c9265bb6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9320000000-6bdc226e79d3bc473a66JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-7bb646a5cb5ca825e7b5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fu-9000000000-ab60a50ef2013d762751JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-ef7c943cff3a9adfd1edJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-0e836f7fe0512bb62662JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059i-9000000000-d1a13699d0d0cbea36b5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-57da9a85ff22593c3ab3JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
  • Urine
Tissue Locations
  • Muscle
  • Stratum Corneum
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
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 Quantified Adult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not Quantified Adult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Associated OMIM IDs
  • 114500 (Colorectal cancer)
  • 601313 (Autosomal dominant polycystic kidney disease)
DrugBank IDDB01775
Phenol Explorer Compound IDNot Available
FoodDB IDFDB009294
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)Download (PDF)
General References
  1. Blake SM, Treble NJ: Popliteus tendon tenosynovitis. Br J Sports Med. 2005 Dec;39(12):e42; discussion e42. [PubMed:16306488 ]
  2. 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. [PubMed:12812295 ]
  3. Phillipou G, Seaborn CJ, Phillips PJ: Re-evaluation of the fructosamine reaction. Clin Chem. 1988 Aug;34(8):1561-4. [PubMed:3402055 ]
  4. 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. [PubMed:10328194 ]
  5. Kerr HH, Pantely GA, Metcalfe J, Welch JE: Reduction of human blood O2 affinity using dihydroxyacetone, phosphate, and pyruvate. J Appl Physiol Respir Environ Exerc Physiol. 1979 Sep;47(3):478-81. [PubMed:118143 ]
  6. 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. [PubMed:6321058 ]
  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. [PubMed:13706567 ]
  8. WITTGENSTEIN E, BERRY HK: Staining of skin with dihydroxyacetone. Science. 1960 Sep 30;132(3431):894-5. [PubMed:13845496 ]
  9. WITTGENSTEIN E, GUEST GM: Biochemical effects of dihydroxyacetone. J Invest Dermatol. 1961 Nov;37:421-6. [PubMed: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