Back to Compounds

Showing Compound Dihydroxyacetone phosphate (FDB001618)

Record Information
Version1.0
Creation date2010-04-08 22:05:02 UTC
Update date2020-09-17 15:38:56 UTC
Primary IDFDB001618
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDihydroxyacetone phosphate
DescriptionDihydroxyacetone phosphate, also known as dihydroxy-acetone-p or 3-hydroxy-2-oxopropyl phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Dihydroxyacetone phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Click on genes, proteins and metabolites below to link to respective articles. It is rapidly and reversibly isomerised to glyceraldehyde 3-phosphate. Dihydroxyacetone phosphate exists in all living species, ranging from bacteria to humans. Within humans, dihydroxyacetone phosphate participates in a number of enzymatic reactions. In particular, ubiquinol-8 and dihydroxyacetone phosphate can be biosynthesized from coenzyme Q10 and glycerol 3-phosphate through the action of the enzyme glycerol-3-phosphate dehydrogenase, mitochondrial. In addition, dihydroxyacetone phosphate can be converted into glycerol 3-phosphate; which is catalyzed by the enzyme glycerol-3-phosphate dehydrogenase [nad(+)], cytoplasmic. Enzyme 5.3.1.1 at KEGG Pathway Database. In humans, dihydroxyacetone phosphate is involved in the metabolic disorder called the mitochondrial electron transport chain pathway. Outside of the human body, Dihydroxyacetone phosphate has been detected, but not quantified in, several different foods, such as cardamoms, dates, red beetroots, oil-seed camellia, and kai-lans. This could make dihydroxyacetone phosphate a potential biomarker for the consumption of these foods. Dihydroxyacetone phosphate is a potentially toxic compound. DHAP is a precursor to 2-oxopropanal. Dihydroxyacetone phosphate, with regard to humans, has been found to be associated with several diseases such as lewy body disease, frontotemporal dementia, and alzheimer's disease; dihydroxyacetone phosphate has also been linked to the inborn metabolic disorder transaldolase deficiency. In the Calvin cycle, DHAP is one of the products of the sixfold reduction of 1,3-bisphosphoglycerate by NADPH. Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is the anion with the formula HOCH2C(O)CH2OPO32-.
CAS Number57-04-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
1-Hydroxy-3-(phosphonooxy)-2-Propanonebiospider
1,3-Dihydroxyacetonephosphatebiospider
2-Propanone, 1-hydroxy-3-(phosphonooxy)biospider
2-Propanone, 1-hydroxy-3-(phosphonooxy)-biospider
2-Propanone, 1,3-dihydroxy-, phosphate (6CI)biospider
3-Hydroxy-2-oxopropyl dihydrogen phosphatebiospider
Dihydroxy-acetone phosphatebiospider
Dihydroxyacetone phosphic acidbiospider
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC3H7O6P
IUPAC name(3-hydroxy-2-oxopropoxy)phosphonic acid
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
Isomeric SMILESOCC(=O)COP(O)(O)=O
Average Molecular Weight170.0578
Monoisotopic Molecular Weight169.998024468
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSDihydroxyacetone phosphate, 1 MEOX; 3 TMS, GC-MS Spectrumsplash10-0uy4-3954100000-ab5b096e0eac9831cf42Spectrum
GC-MSDihydroxyacetone phosphate, 1 MEOX; 3 TMS, GC-MS Spectrumsplash10-0g0m-3964100000-cd938c4cea382029ce88Spectrum
GC-MSDihydroxyacetone phosphate, non-derivatized, GC-MS Spectrumsplash10-0uy4-3954100000-ab5b096e0eac9831cf42Spectrum
GC-MSDihydroxyacetone phosphate, non-derivatized, GC-MS Spectrumsplash10-0g0m-3964100000-cd938c4cea382029ce88Spectrum
Predicted GC-MSDihydroxyacetone phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ot-9400000000-a02e9df63512a60b9324Spectrum
Predicted GC-MSDihydroxyacetone phosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9200000000-79dfc0ac375f4d056dc9Spectrum
Predicted GC-MSDihydroxyacetone phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kb-9600000000-050f206e1fed5aaa8c1f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9100000000-c7eb3c008e10f8e153862017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-0f8d50d1d029df4e6c432017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-7c2d8125a273e3fae4f62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-517dcdb0a35f00b4b4912017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9000000000-b8d3aeb9415528f3d0352017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0udi-2900000000-6091e72aad27af4c79712020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-00fr-0900000000-b948afb7a993bfbaf1df2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-7900000000-fec8dd084ee59efa22862015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9800000000-beb639c3fffc815897cc2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9000000000-580658c1ae323fa4f7182015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-6900000000-4a0e75761c8eb8071d1e2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-7e5e1e00ef8f891ffe3e2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-08f155d8875692abc94b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-7900000000-fec8dd084ee59efa22862015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9800000000-beb639c3fffc815897cc2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9000000000-580658c1ae323fa4f7182015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-6900000000-4a0e75761c8eb8071d1e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-7e5e1e00ef8f891ffe3e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-08f155d8875692abc94b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9100000000-83b3c3bba9003d67c4442021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fdk-9800000000-dad61e875fa6524224d82021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007k-9200000000-3ce8b7e1264e4e13f7922021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00111
Pubchem Compound ID668
Pubchem Substance IDNot Available
ChEBI ID16108
Phenol-Explorer IDNot Available
DrugBank IDDB04326
HMDB IDHMDB01473
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33898
KNApSAcK IDC00007560
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDihydroxyacetone phosphate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.