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Human Metabolome Database Version 3.5

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Showing metabocard for Dihydroxyacetone phosphate (HMDB01473)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:37 -0700
HMDB ID HMDB01473
Secondary Accession Numbers
  • HMDB11735
Metabolite Identification
Common Name Dihydroxyacetone phosphate
Description Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,3-Dihydroxy-2-Propanone mono(dihydrogen phosphate)
  2. 1,3-Dihydroxy-2-propanone phosphate
  3. 1,3-Dihydroxyacetone 1-phosphate
  4. 1-Hydroxy-3-(phosphonooxy)-2-Propanone
  5. 1-Hydroxy-3-(phosphonooxy)acetone
  6. DHAP
  7. Di-OH-acetone-P
  8. Dihydroxy-Acetone-P
  9. Dihydroxy-acetone-phosphate
  10. Dihydroxyacetone 3-phosphate
  11. Dihydroxyacetone monophosphate
  12. Dihydroxyacetone phosphate
  13. Dihydroxyacetone-P
  14. Dihydroxyacetone-phosphate
  15. Glycerone phosphate
  16. Glycerone-phosphate
  17. Phosphoric acid ester with 1,3-dihydroxy-2-propanone
Chemical Formula C3H7O6P
Average Molecular Weight 170.0578
Monoisotopic Molecular Weight 169.998024468
IUPAC Name (3-hydroxy-2-oxopropoxy)phosphonic acid
Traditional IUPAC Name 3-hydroxy-2-oxopropoxyphosphonic acid
CAS Registry Number 57-04-5
SMILES OCC(=O)COP(O)(O)=O
InChI Identifier InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
InChI Key GNGACRATGGDKBX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organophosphorus Compounds
Class Organic Phosphoric Acids and Derivatives
Sub Class Organophosphate Esters
Other Descriptors
  • Aliphatic Acyclic Compounds
  • glycerone phosphates(ChEBI)
Substituents
  • Alpha Ketoaldehyde
  • Ketone
  • Organic Hypophosphite
  • Organic Phosphite
  • Primary Alcohol
Direct Parent Organophosphate Esters
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
  • Component of Glycerophospholipid metabolism
  • Component of Inositol metabolism
Application Not Available
Cellular locations
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 21.9 g/L ALOGPS
LogP -1.49 ALOGPS
LogP -1.7 ChemAxon
LogS -0.89 ALOGPS
pKa (strongest acidic) 1.19 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 104.06 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 30.47 ChemAxon
Polarizability 12.64 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations
  • Peroxisome
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Fructose and Mannose Degradation SMP00064 map00051 Link_out
Glycerol Phosphate Shuttle SMP00124 Not Available
Mitochondrial Electron Transport Chain SMP00355 map00190 Link_out
Phospholipid Biosynthesis SMP00025 map00564 Link_out
Glycerolipid Metabolism SMP00039 map00561 Link_out
Glycolysis SMP00040 map00010 Link_out
Gluconeogenesis SMP00128 map00010 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
12.1 +/- 5.1 uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
15.6 +/- 4.56 uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
Article_icon
140 (60-220) uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
1.88 +/- 0.34 uM Adult (>18 years old) Both Transaldolase deficiency Not Available
Associated Disorders and Diseases
Disease References
Transaldolase deficiency
  • Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. Pubmed: 12881455 Link_out
    Associated OMIM IDs
    • 606003 Link_out (Transaldolase deficiency)
    DrugBank ID DB04326 Link_out
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB001618
    KNApSAcK ID C00007560 Link_out
    Chemspider ID 648 Link_out
    KEGG Compound ID C00111 Link_out
    BioCyc ID DIHYDROXY-ACETONE-PHOSPHATE Link_out
    BiGG ID 33898 Link_out
    Wikipedia Link Dihydroxyacetone phosphate Link_out
    NuGOwiki Link HMDB01473 Link_out
    Metagene Link HMDB01473 Link_out
    METLIN ID 6262 Link_out
    PubChem Compound 668 Link_out
    PDB ID 13P Link_out
    ChEBI ID 16108 Link_out
    References
    Synthesis Reference Ballou, Clinton E.; Fischer, Hermann O. L. The synthesis of dihydroxyacetone phosphate. Journal of the American Chemical Society (1956), 78 1659-61.
    Material Safety Data Sheet (MSDS) Not Available
    General References
    1. 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. Pubmed: 1332571 Link_out
    2. 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. Pubmed: 8931639 Link_out
    3. 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. Pubmed: 3119940 Link_out
    4. 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(1):18. Pubmed: 15882454 Link_out
    Enzymes
    Name: Alkaline phosphatase, placental type
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ALPP
    Uniprot ID: P05187 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Intestinal-type alkaline phosphatase
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ALPI
    Uniprot ID: P09923 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alkaline phosphatase, tissue-nonspecific isozyme
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ALPL
    Uniprot ID: P05186 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alkaline phosphatase, placental-like
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ALPPL2
    Uniprot ID: P10696 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glycerol-3-phosphate dehydrogenase, mitochondrial
    Reactions:
    • sn-glycerol 3-phosphate + a quinone = glycerone phosphate + a quinol [RN:R00849]
    Gene Name: GPD2
    Uniprot ID: P43304 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glycerol-3-phosphate dehydrogenase [NAD+], cytoplasmic
    Reactions:
    • sn-glycerol 3-phosphate + NAD+ = glycerone phosphate + NADH + H+ [RN:R00842]
    Gene Name: GPD1
    Uniprot ID: P21695 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Fructose-bisphosphate aldolase A
    Reactions:
    • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
    Gene Name: ALDOA
    Uniprot ID: P04075 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Fructose-bisphosphate aldolase C
    Reactions:
    • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
    Gene Name: ALDOC
    Uniprot ID: P09972 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Fructose-bisphosphate aldolase B
    Reactions:
    • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
    Gene Name: ALDOB
    Uniprot ID: P05062 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Dihydroxyacetone phosphate acyltransferase
    Reactions:
    • acyl-CoA + glycerone phosphate = CoA + acylglycerone phosphate [RN:R01013]
    Gene Name: GNPAT
    Uniprot ID: O15228 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Triosephosphate isomerase
    Reactions:
    • D-glyceraldehyde 3-phosphate = glycerone phosphate [RN:R01015]
    Gene Name: TPI1
    Uniprot ID: P60174 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)
    Reactions:
    • FAD = AMP + riboflavin cyclic-4',5'-phosphate [RN:R07636]
    Gene Name: DAK
    Uniprot ID: Q3LXA3 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glycerol-3-phosphate dehydrogenase 1-like protein
    Reactions:
    • sn-glycerol 3-phosphate + NAD+ = glycerone phosphate + NADH + H+ [RN:R00842]
    Gene Name: GPD1L
    Uniprot ID: Q8N335 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Triosephosphate isomerase
    Reactions:
    • D-glyceraldehyde 3-phosphate = glycerone phosphate [RN:R01015]
    Gene Name: Not Available
    Uniprot ID: Q2QD09 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA