Dihydroxyacetone phosphate (CHEM003429)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2014-08-29 06:51:34 UTC
Update Date2026-05-14 18:07:38 UTC
Accession NumberCHEM003429
Identification
Common NameDihydroxyacetone phosphate
ClassSmall Molecule
DescriptionDihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Food Toxin
  • Ketone
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3-Dihydroxy-2-propanone monodihydrogen phosphateChEBI
1,3-Dihydroxy-2-propanone phosphateChEBI
1,3-Dihydroxyacetone 1-phosphateChEBI
1-Hydroxy-3-(phosphonooxy)-2-propanoneChEBI
1-Hydroxy-3-(phosphonooxy)acetoneChEBI
3-Hydroxy-2-oxopropyl phosphateChEBI
DHAPChEBI
Dihydroxyacetone monophosphateChEBI
Glycerone monophosphateChEBI
Glycerone phosphateChEBI
1,3-Dihydroxy-2-propanone monodihydrogen phosphoric acidGenerator
1,3-Dihydroxy-2-propanone phosphoric acidGenerator
1,3-Dihydroxyacetone 1-phosphoric acidGenerator
3-Hydroxy-2-oxopropyl phosphoric acidGenerator
Dihydroxyacetone monophosphoric acidGenerator
Glycerone monophosphoric acidGenerator
Glycerone phosphoric acidGenerator
Dihydroxyacetone phosphoric acidGenerator
1,3-Dihydroxy-2-propanone mono(dihydrogen phosphate)HMDB
Di-OH-acetone-pHMDB
Dihydroxy-acetone-pHMDB
Dihydroxy-acetone-phosphateHMDB
Dihydroxyacetone 3-phosphateHMDB
Dihydroxyacetone-pHMDB
Dihydroxyacetone-phosphateHMDB
Glycerone-phosphateHMDB
Phosphoric acid ester with 1,3-dihydroxy-2-propanoneHMDB
3-Phosphate, dihydroxyacetoneHMDB
Phosphate, dihydroxyacetoneHMDB
Dihydroxyacetone 3 phosphateHMDB
Chemical FormulaC3H7O6P
Average Molecular Mass170.058 g/mol
Monoisotopic Mass169.998 g/mol
CAS Registry Number57-04-5
IUPAC Name(3-hydroxy-2-oxopropoxy)phosphonic acid
Traditional Namedihydroxyacetone-phosphate
SMILESOCC(=O)COP(O)(O)=O
InChI IdentifierInChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
InChI KeyGNGACRATGGDKBX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Glycerone phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Glycerone or derivatives
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Alpha-hydroxy ketone
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Peroxisome
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064 map00051
GluconeogenesisSMP00128 Not Available
Glycerol Phosphate ShuttleSMP00124 Not Available
Glycerolipid MetabolismSMP00039 map00561
GlycolysisSMP00040 Not Available
Mitochondrial Electron Transport ChainSMP00355 map00190
Phospholipid BiosynthesisSMP00025 map00564
Triosephosphate isomeraseSMP00563 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility21.9 g/LALOGPS
logP-1.5ALOGPS
logP-1.7ChemAxon
logS-0.89ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.47 m³·mol⁻¹ChemAxon
Polarizability12.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0uy4-3954100000-ab5b096e0eac9831cf42Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0g0m-3964100000-cd938c4cea382029ce88Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uy4-3954100000-ab5b096e0eac9831cf42Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0g0m-3964100000-cd938c4cea382029ce88Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-9400000000-a02e9df63512a60b9324Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9200000000-79dfc0ac375f4d056dc9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kb-9600000000-050f206e1fed5aaa8c1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9100000000-c7eb3c008e10f8e15386Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-0f8d50d1d029df4e6c43Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-7c2d8125a273e3fae4f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-517dcdb0a35f00b4b491Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9000000000-b8d3aeb9415528f3d035Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0udi-2900000000-6091e72aad27af4c7971Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-00fr-0900000000-b948afb7a993bfbaf1dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-7900000000-fec8dd084ee59efa2286Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9800000000-beb639c3fffc815897ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9000000000-580658c1ae323fa4f718Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-6900000000-4a0e75761c8eb8071d1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-7e5e1e00ef8f891ffe3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-08f155d8875692abc94bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-7900000000-fec8dd084ee59efa2286Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9800000000-beb639c3fffc815897ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9000000000-580658c1ae323fa4f718Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-6900000000-4a0e75761c8eb8071d1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-7e5e1e00ef8f891ffe3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-08f155d8875692abc94bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9100000000-83b3c3bba9003d67c444Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fdk-9800000000-dad61e875fa6524224d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007k-9200000000-3ce8b7e1264e4e13f792Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04326
HMDB IDHMDB0001473
FooDB IDFDB001618
Phenol Explorer IDNot Available
KNApSAcK IDC00007560
BiGG ID33898
BioCyc IDDIHYDROXY-ACETONE-PHOSPHATE
METLIN ID6262
PDB IDNot Available
Wikipedia LinkDihydroxyacetone_phosphate
Chemspider ID648
ChEBI ID16108
PubChem Compound ID668
Kegg Compound IDC00111
YMDB IDYMDB00322
ECMDB IDECMDB01473
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ballou, Clinton E.; Fischer, Hermann O. L. The synthesis of dihydroxyacetone phosphate. Journal of the American Chemical Society (1956), 78 1659-61.
2. Roberts NB, Dutton J, Helliwell T, Rothwell PJ, Kavanagh JP: Pyrophosphate in synovial fluid and urine and its relationship to urinary risk factors for stone disease. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):529-34.
3. Yamamoto T, Moriwaki Y, Takahashi S, Ohata H, Nakano T, Yamakita J, Higashino K: Effect of glucagon on the xylitol-induced increase in the plasma concentration and urinary excretion of purine bases. Metabolism. 1996 Nov;45(11):1354-9.
4. Schutgens RB, Wanders RJ, Heymans HS, Schram AW, Tager JM, Schrakamp G, van den Bosch H: Zellweger syndrome: biochemical procedures in diagnosis, prevention and treatment. J Inherit Metab Dis. 1987;10 Suppl 1:33-45.
5. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18.
6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=10098675
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=1332571
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=20092811