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Showing metabocard for Dihydroxyacetone phosphate (HMDB0001473)

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enzymes (14) Show 14 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:44 UTC
HMDB IDHMDB0001473
Secondary Accession Numbers
  • HMDB0011735
  • HMDB01473
  • HMDB11735
Metabolite Identification
Common 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-.
Structure
Data?1676999744
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001473 (Dihydroxyacetone phosphate)


  Mrv1652309042000232D          

 10  9  0  0  0  0            999 V2000
    1.7605   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
M  END
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3D MOL for HMDB0001473 (Dihydroxyacetone phosphate)

HMDB0001473
     RDKit          3D
Dihydroxyacetone phosphate
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.7026   -2.3212   -0.6356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3799   -1.2037   -0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3761   -0.3955    0.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9038    0.8472    0.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0238   -0.7384   -0.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2437    0.5374   -0.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8328    0.9420   -0.5494 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.8858    1.0821   -2.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2788    2.4392    0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9379   -0.2113   -0.0131 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2720   -0.2250   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535   -0.8913    1.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788    0.8405    1.7106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1229   -0.8482   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6971   -1.4498   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4219    2.3684    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4696   -0.7723    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  7 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  9 16  1  0
 10 17  1  0
M  END
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3D SDF for HMDB0001473 (Dihydroxyacetone phosphate)


  Mrv1652309042000232D          

 10  9  0  0  0  0            999 V2000
    1.7605   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001473

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C3H7O6P

> <MOLECULAR_WEIGHT>
170.0578

> <EXACT_MASS>
169.998024468

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.641516377396067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3-hydroxy-2-oxopropoxy)phosphonic acid

> <ALOGPS_LOGP>
-1.49

> <JCHEM_LOGP>
-1.6517823150000002

> <ALOGPS_LOGS>
-0.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.220373471836065

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1902795898513006

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3227461112640855

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
30.472099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.19e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydroxyacetone-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001473 (Dihydroxyacetone phosphate)

HMDB0001473
     RDKit          3D
Dihydroxyacetone phosphate
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.7026   -2.3212   -0.6356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3799   -1.2037   -0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3761   -0.3955    0.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9038    0.8472    0.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0238   -0.7384   -0.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2437    0.5374   -0.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8328    0.9420   -0.5494 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.8858    1.0821   -2.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2788    2.4392    0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9379   -0.2113   -0.0131 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2720   -0.2250   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535   -0.8913    1.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788    0.8405    1.7106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1229   -0.8482   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6971   -1.4498   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4219    2.3684    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4696   -0.7723    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  7 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  9 16  1  0
 10 17  1  0
M  END
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PDB for HMDB0001473 (Dihydroxyacetone phosphate)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0       3.286  -3.437   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.954  -3.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.954  -4.977   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.621  -3.437   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0       9.955  -2.667   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      11.288  -1.897   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      10.725  -4.001   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       9.185  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0001473 (Dihydroxyacetone phosphate)

COMPND    HMDB0001473
HETATM    1  O1  UNL     1       1.703  -2.321  -0.636  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.380  -1.204  -0.269  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.376  -0.395   0.462  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.904   0.847   0.826  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.024  -0.738  -0.580  1.00  0.00           C  
HETATM    6  O3  UNL     1      -0.244   0.537  -0.124  1.00  0.00           O  
HETATM    7  P1  UNL     1      -1.833   0.942  -0.549  1.00  0.00           P  
HETATM    8  O4  UNL     1      -1.886   1.082  -2.064  1.00  0.00           O  
HETATM    9  O5  UNL     1      -2.279   2.439   0.094  1.00  0.00           O  
HETATM   10  O6  UNL     1      -2.938  -0.211  -0.013  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.272  -0.225  -0.188  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.753  -0.891   1.378  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.479   0.840   1.711  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.123  -0.848  -1.683  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.697  -1.450  -0.085  1.00  0.00           H  
HETATM   16  H6  UNL     1      -2.422   2.368   1.058  1.00  0.00           H  
HETATM   17  H7  UNL     1      -2.470  -0.772   0.664  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    5
CONECT    3    4   11   12
CONECT    4   13
CONECT    5    6   14   15
CONECT    6    7
CONECT    7    8    8    9   10
CONECT    9   16
CONECT   10   17
END
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SMILES for HMDB0001473 (Dihydroxyacetone phosphate)

OCC(=O)COP(O)(O)=O
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INCHI for HMDB0001473 (Dihydroxyacetone phosphate)

InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
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View in JSmolView NMR AssignmentsView Stereo Labels
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 Weight170.0578
Monoisotopic Molecular Weight169.998024468
IUPAC Name(3-hydroxy-2-oxopropoxy)phosphonic acid
Traditional Namedihydroxyacetone-phosphate
CAS Registry Number57-04-5
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 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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.30831661259
DarkChem[M-H]-129.85331661259
AllCCS[M+H]+136.3932859911
AllCCS[M-H]-128.45932859911
DeepCCS[M+H]+123.91530932474
DeepCCS[M-H]-120.75530932474
DeepCCS[M-2H]-157.82230932474
DeepCCS[M+Na]+132.66930932474
AllCCS[M+H]+136.432859911
AllCCS[M+H-H2O]+132.532859911
AllCCS[M+NH4]+140.032859911
AllCCS[M+Na]+141.132859911
AllCCS[M-H]-128.532859911
AllCCS[M+Na-2H]-130.732859911
AllCCS[M+HCOO]-133.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.12 minutes32390414
Predicted by Siyang on May 30, 20228.6793 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20228.81 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid380.6 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid471.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid317.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid42.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid204.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid65.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid270.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid219.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)808.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid557.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid37.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid632.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid198.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid275.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate726.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA377.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water415.8 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihydroxyacetone phosphateOCC(=O)COP(O)(O)=O2663.5Standard polar33892256
Dihydroxyacetone phosphateOCC(=O)COP(O)(O)=O1394.3Standard non polar33892256
Dihydroxyacetone phosphateOCC(=O)COP(O)(O)=O1541.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydroxyacetone phosphate,1TMS,isomer #1C[Si](C)(C)OCC(=O)COP(=O)(O)O1596.3Semi standard non polar33892256
Dihydroxyacetone phosphate,1TMS,isomer #2C[Si](C)(C)OP(=O)(O)OCC(=O)CO1600.3Semi standard non polar33892256
Dihydroxyacetone phosphate,1TMS,isomer #3C[Si](C)(C)OC(=COP(=O)(O)O)CO1651.5Semi standard non polar33892256
Dihydroxyacetone phosphate,1TMS,isomer #4C[Si](C)(C)OC(=CO)COP(=O)(O)O1668.5Semi standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #1C[Si](C)(C)OCC(=O)COP(=O)(O)O[Si](C)(C)C1694.9Semi standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #1C[Si](C)(C)OCC(=O)COP(=O)(O)O[Si](C)(C)C1611.0Standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #1C[Si](C)(C)OCC(=O)COP(=O)(O)O[Si](C)(C)C2082.5Standard polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #2C[Si](C)(C)OCC(=COP(=O)(O)O)O[Si](C)(C)C1688.3Semi standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #2C[Si](C)(C)OCC(=COP(=O)(O)O)O[Si](C)(C)C1705.8Standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #2C[Si](C)(C)OCC(=COP(=O)(O)O)O[Si](C)(C)C2369.6Standard polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #3C[Si](C)(C)OC=C(COP(=O)(O)O)O[Si](C)(C)C1751.8Semi standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #3C[Si](C)(C)OC=C(COP(=O)(O)O)O[Si](C)(C)C1715.5Standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #3C[Si](C)(C)OC=C(COP(=O)(O)O)O[Si](C)(C)C2483.5Standard polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #4C[Si](C)(C)OP(=O)(OCC(=O)CO)O[Si](C)(C)C1655.8Semi standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #4C[Si](C)(C)OP(=O)(OCC(=O)CO)O[Si](C)(C)C1597.3Standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #4C[Si](C)(C)OP(=O)(OCC(=O)CO)O[Si](C)(C)C1897.8Standard polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #5C[Si](C)(C)OC(=CO)COP(=O)(O)O[Si](C)(C)C1720.1Semi standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #5C[Si](C)(C)OC(=CO)COP(=O)(O)O[Si](C)(C)C1677.4Standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #5C[Si](C)(C)OC(=CO)COP(=O)(O)O[Si](C)(C)C2233.0Standard polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #6C[Si](C)(C)OC(=COP(=O)(O)O[Si](C)(C)C)CO1700.2Semi standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #6C[Si](C)(C)OC(=COP(=O)(O)O[Si](C)(C)C)CO1670.7Standard non polar33892256
Dihydroxyacetone phosphate,2TMS,isomer #6C[Si](C)(C)OC(=COP(=O)(O)O[Si](C)(C)C)CO2220.3Standard polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #1C[Si](C)(C)OCC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1753.6Semi standard non polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #1C[Si](C)(C)OCC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1676.1Standard non polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #1C[Si](C)(C)OCC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1779.4Standard polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #2C[Si](C)(C)OCC(=COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C1762.1Semi standard non polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #2C[Si](C)(C)OCC(=COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C1706.1Standard non polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #2C[Si](C)(C)OCC(=COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C1982.0Standard polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #3C[Si](C)(C)OC=C(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C1792.8Semi standard non polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #3C[Si](C)(C)OC=C(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C1686.2Standard non polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #3C[Si](C)(C)OC=C(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2059.2Standard polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #4C[Si](C)(C)OC(=CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1757.3Semi standard non polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #4C[Si](C)(C)OC(=CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1756.4Standard non polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #4C[Si](C)(C)OC(=CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1890.1Standard polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #5C[Si](C)(C)OC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CO1739.1Semi standard non polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #5C[Si](C)(C)OC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CO1724.4Standard non polar33892256
Dihydroxyacetone phosphate,3TMS,isomer #5C[Si](C)(C)OC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CO1879.4Standard polar33892256
Dihydroxyacetone phosphate,4TMS,isomer #1C[Si](C)(C)OCC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C1810.6Semi standard non polar33892256
Dihydroxyacetone phosphate,4TMS,isomer #1C[Si](C)(C)OCC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C1758.4Standard non polar33892256
Dihydroxyacetone phosphate,4TMS,isomer #1C[Si](C)(C)OCC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C1761.0Standard polar33892256
Dihydroxyacetone phosphate,4TMS,isomer #2C[Si](C)(C)OC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C1833.6Semi standard non polar33892256
Dihydroxyacetone phosphate,4TMS,isomer #2C[Si](C)(C)OC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C1740.3Standard non polar33892256
Dihydroxyacetone phosphate,4TMS,isomer #2C[Si](C)(C)OC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C1843.8Standard polar33892256
Dihydroxyacetone phosphate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)COP(=O)(O)O1843.2Semi standard non polar33892256
Dihydroxyacetone phosphate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(O)OCC(=O)CO1852.0Semi standard non polar33892256
Dihydroxyacetone phosphate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=COP(=O)(O)O)CO1905.0Semi standard non polar33892256
Dihydroxyacetone phosphate,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CO)COP(=O)(O)O1888.1Semi standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C2109.2Semi standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C2052.8Standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C2316.7Standard polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(=COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2161.1Semi standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(=COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2093.4Standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(=COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2539.7Standard polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2150.4Semi standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2132.4Standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2634.7Standard polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(OCC(=O)CO)O[Si](C)(C)C(C)(C)C2101.4Semi standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(OCC(=O)CO)O[Si](C)(C)C(C)(C)C2021.1Standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(OCC(=O)CO)O[Si](C)(C)C(C)(C)C2137.5Standard polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=CO)COP(=O)(O)O[Si](C)(C)C(C)(C)C2156.2Semi standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=CO)COP(=O)(O)O[Si](C)(C)C(C)(C)C2114.6Standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=CO)COP(=O)(O)O[Si](C)(C)C(C)(C)C2402.7Standard polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)CO2170.6Semi standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)CO2078.6Standard non polar33892256
Dihydroxyacetone phosphate,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)CO2395.1Standard polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2356.5Semi standard non polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2255.6Standard non polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2142.5Standard polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2376.9Semi standard non polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2265.8Standard non polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2300.8Standard polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2390.6Semi standard non polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2274.9Standard non polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2329.7Standard polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2373.9Semi standard non polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2317.1Standard non polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2213.3Standard polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2360.0Semi standard non polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2255.4Standard non polar33892256
Dihydroxyacetone phosphate,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CO2205.0Standard polar33892256
Dihydroxyacetone phosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2564.2Semi standard non polar33892256
Dihydroxyacetone phosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2406.8Standard non polar33892256
Dihydroxyacetone phosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2202.9Standard polar33892256
Dihydroxyacetone phosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2592.2Semi standard non polar33892256
Dihydroxyacetone phosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2402.3Standard non polar33892256
Dihydroxyacetone phosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2243.6Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Peroxisome
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified12.1 +/- 5.1 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified15.6 +/- 4.56 uMAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified140 (60-220) uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified10.33 +/- 5.13 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified1.87 +/- 0.809 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified2.08 +/- 1.62 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified3.00 +/- 1.57 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified3.68 +/- 1.39 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.88 +/- 0.34 uMAdult (>18 years old)BothTransaldolase deficiency details
SalivaDetected and Quantified8.45 +/- 4.68 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified10.80 +/- 9.74 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified8.71 +/- 3.88 uMAdult (>18 years old)BothLewy body disease details
Associated Disorders and Diseases
Disease References
Transaldolase deficiency
  1. 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 ]
Alzheimer's disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Associated OMIM IDs
DrugBank IDDB04326
Phenol Explorer Compound IDNot Available
FooDB IDFDB001618
KNApSAcK IDC00007560
Chemspider ID648
KEGG Compound IDC00111
BioCyc IDDIHYDROXY-ACETONE-PHOSPHATE
BiGG ID33898
Wikipedia LinkDihydroxyacetone_phosphate
METLIN ID6262
PubChem Compound668
PDB IDNot Available
ChEBI ID16108
Food Biomarker OntologyNot Available
VMH IDDHAP
MarkerDB IDMDB00000328
Good Scents IDNot Available
References
Synthesis ReferenceBallou, 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. 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. [PubMed:15882454 ]
  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. [PubMed:1332571 ]
  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. [PubMed:8931639 ]
  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. [PubMed:3119940 ]
  5. 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. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Alkaline phosphatase, placental type
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPP
Uniprot ID:
P05187
Molecular weight:
57953.31
Enzyme Details
2. Intestinal-type alkaline phosphatase
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPI
Uniprot ID:
P09923
Molecular weight:
56811.695
Enzyme Details
3. Alkaline phosphatase, tissue-nonspecific isozyme
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
Enzyme Details
4. Alkaline phosphatase, placental-like
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
Enzyme Details
5. Glycerol-3-phosphate dehydrogenase, mitochondrial
General function:
Involved in calcium ion binding
Specific function:
Not Available
Gene Name:
GPD2
Uniprot ID:
P43304
Molecular weight:
80851.99
Reactions
Glycerol 3-phosphate + a quinone → Dihydroxyacetone phosphate + a quinoldetails
Glycerol 3-phosphate + FAD → Dihydroxyacetone phosphate + FADHdetails
Enzyme Details
6. Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
GPD1
Uniprot ID:
P21695
Molecular weight:
37567.4
Reactions
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADHdetails
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADH + Hydrogen Iondetails
Enzyme Details
7. Fructose-bisphosphate aldolase A
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Plays a key role in glycolysis and gluconeogenesis. In addition, may also function as scaffolding protein (By similarity).
Gene Name:
ALDOA
Uniprot ID:
P04075
Molecular weight:
39419.675
Reactions
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + Glyceraldehyde 3-phosphatedetails
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + Glyceraldehyde 3-phosphatedetails
Sedoheptulose 1,7-bisphosphate → Dihydroxyacetone phosphate + D-Erythrose 4-phosphatedetails
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
Dihydroxyacetone phosphate + D-Erythrose 4-phosphate → Sedoheptulose 1,7-bisphosphatedetails
Dihydroxyacetone phosphate + Glyceraldehyde 3-phosphate → Fructose 1,6-bisphosphatedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Enzyme Details
8. Fructose-bisphosphate aldolase C
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Not Available
Gene Name:
ALDOC
Uniprot ID:
P09972
Molecular weight:
39455.505
Reactions
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + Glyceraldehyde 3-phosphatedetails
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + Glyceraldehyde 3-phosphatedetails
Sedoheptulose 1,7-bisphosphate → Dihydroxyacetone phosphate + D-Erythrose 4-phosphatedetails
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
Enzyme Details
9. Fructose-bisphosphate aldolase B
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
P05062
Molecular weight:
39472.715
Reactions
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + Glyceraldehyde 3-phosphatedetails
Fructose 1,6-bisphosphate → Dihydroxyacetone phosphate + Glyceraldehyde 3-phosphatedetails
Sedoheptulose 1,7-bisphosphate → Dihydroxyacetone phosphate + D-Erythrose 4-phosphatedetails
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Enzyme Details
10. Dihydroxyacetone phosphate acyltransferase
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
GNPAT
Uniprot ID:
O15228
Molecular weight:
77187.185
Reactions
Acyl-CoA + Dihydroxyacetone phosphate → Coenzyme A + acylglycerone phosphatedetails

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters