Bovine Metabolome Database: Showing metabocard for Dihydroxyacetone phosphate (BMDB0001473)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (10) Show 10 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:46:27 UTC

Update Date

2020-05-21 16:29:07 UTC

BMDB ID

BMDB0001473

Secondary Accession Numbers

BMDB01473

Metabolite Identification

Common Name

Dihydroxyacetone phosphate

Description

Dihydroxyacetone phosphate, also known as Dihydroxyacetone phosphate or Dihydroxyacetone 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 possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydroxyacetone phosphate exists in all living species, ranging from bacteria to humans. Dihydroxyacetone phosphate participates in a number of enzymatic reactions, within cattle. 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 through its interaction with the enzyme glycerol-3-phosphate dehydrogenase [nad(+)], cytoplasmic. In cattle, dihydroxyacetone phosphate is involved in the metabolic pathway called the mitochondrial electron transport chain pathway. Dihydroxyacetone phosphate is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3-Dihydroxy-2-propanone monodihydrogen phosphate	ChEBI
1,3-Dihydroxy-2-propanone phosphate	ChEBI
1,3-Dihydroxyacetone 1-phosphate	ChEBI
1-Hydroxy-3-(phosphonooxy)-2-propanone	ChEBI
1-Hydroxy-3-(phosphonooxy)acetone	ChEBI
3-Hydroxy-2-oxopropyl phosphate	ChEBI
DHAP	ChEBI
Dihydroxyacetone monophosphate	ChEBI
Glycerone monophosphate	ChEBI
Glycerone phosphate	ChEBI
1,3-Dihydroxy-2-propanone monodihydrogen phosphoric acid	Generator
1,3-Dihydroxy-2-propanone phosphoric acid	Generator
1,3-Dihydroxyacetone 1-phosphoric acid	Generator
3-Hydroxy-2-oxopropyl phosphoric acid	Generator
Dihydroxyacetone monophosphoric acid	Generator
Glycerone monophosphoric acid	Generator
Glycerone phosphoric acid	Generator
Dihydroxyacetone phosphoric acid	Generator
1,3-Dihydroxy-2-propanone mono(dihydrogen phosphate)	HMDB
Di-OH-acetone-p	HMDB
Dihydroxy-acetone-p	HMDB
Dihydroxy-acetone-phosphate	HMDB
Dihydroxyacetone 3-phosphate	HMDB
Dihydroxyacetone-p	HMDB
Dihydroxyacetone-phosphate	HMDB
Glycerone-phosphate	HMDB
Phosphoric acid ester with 1,3-dihydroxy-2-propanone	HMDB
3-Phosphate, dihydroxyacetone	HMDB
Phosphate, dihydroxyacetone	HMDB
Dihydroxyacetone 3 phosphate	HMDB

Chemical Formula

C₃H₇O₆P

Average Molecular Weight

170.0578

Monoisotopic Molecular Weight

169.998024468

IUPAC Name

(3-hydroxy-2-oxopropoxy)phosphonic acid

Traditional Name

dihydroxyacetone-phosphate

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

Description

belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide 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 Framework

Aliphatic acyclic compounds

External Descriptors

glycerone phosphates (CHEBI:16108 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria
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
logP	-1.5	ALOGPS
logP	-1.7	ChemAxon
logS	-0.89	ALOGPS
pKa (Strongest Acidic)	1.19	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	30.47 m³·mol⁻¹	ChemAxon
Polarizability	12.64 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-0uy4-3954100000-ab5b096e0eac9831cf42	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-0g0m-3964100000-cd938c4cea382029ce88	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0uy4-3954100000-ab5b096e0eac9831cf42	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0g0m-3964100000-cd938c4cea382029ce88	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-9400000000-a02e9df63512a60b9324	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0002-9200000000-79dfc0ac375f4d056dc9	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kb-9600000000-050f206e1fed5aaa8c1f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9100000000-c7eb3c008e10f8e15386	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-0f8d50d1d029df4e6c43	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-7c2d8125a273e3fae4f6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-517dcdb0a35f00b4b491	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9000000000-b8d3aeb9415528f3d035	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0udi-2900000000-6091e72aad27af4c7971	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-00fr-0900000000-b948afb7a993bfbaf1df	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-7900000000-fec8dd084ee59efa2286	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kmi-9800000000-beb639c3fffc815897cc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9000000000-580658c1ae323fa4f718	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016r-6900000000-4a0e75761c8eb8071d1e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-7e5e1e00ef8f891ffe3e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-08f155d8875692abc94b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-7900000000-fec8dd084ee59efa2286	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kmi-9800000000-beb639c3fffc815897cc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9000000000-580658c1ae323fa4f718	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016r-6900000000-4a0e75761c8eb8071d1e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-7e5e1e00ef8f891ffe3e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-08f155d8875692abc94b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9100000000-83b3c3bba9003d67c444	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fdk-9800000000-dad61e875fa6524224d8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-007k-9200000000-3ce8b7e1264e4e13f792	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria
Peroxisome

Biospecimen Locations

Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis		Not Available
Cardiolipin Biosynthesis		Not Available
De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:1(9Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/15:0)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001473

DrugBank ID

DB04326

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

DIHYDROXY-ACETONE-PHOSPHATE

BiGG ID

33898

Wikipedia Link

Dihydroxyacetone_phosphate

METLIN ID

6262

PubChem Compound

668

PDB ID

Not Available

ChEBI ID

16108

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

Not Available

Enzymes

Enzyme Details

1. Glycerol-3-phosphate dehydrogenase, mitochondrial

General function:: Energy production and conversion
Specific function:: Not Available
Gene Name:: GPD2
Uniprot ID:: A6QLU1
Molecular weight:: 80763.0

Reactions

Glycerol 3-phosphate + Quinone → Dihydroxyacetone phosphate + Hydroquinone	details
Dihydroxyacetone phosphate + Quinone → Glycerol 3-phosphate + Hydroquinone	details
Coenzyme Q10 + Glycerol 3-phosphate → Ubiquinol + Dihydroxyacetone phosphate	details

Enzyme Details

2. Dihydroxyacetone phosphate acyltransferase

General function:: Lipid transport and metabolism
Specific function:: Not Available
Gene Name:: GNPAT
Uniprot ID:: A4IF87
Molecular weight:: 77664.0

Reactions

Eicosanoyl-CoA + Dihydroxyacetone phosphate → DHAP(18:0) + Coenzyme A	details

Enzyme Details

3. Triokinase/FMN cyclase

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. Represses IFIH1-mediated cellular antiviral response.
Gene Name:: TKFC
Uniprot ID:: Q58DK4
Molecular weight:: 59124.0

Enzyme Details

4. Fructose-bisphosphate aldolase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: ALDOA
Uniprot ID:: A6QLL8
Molecular weight:: 39436.0

Enzyme Details

5. Fructose-bisphosphate aldolase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: ALDOC
Uniprot ID:: Q3ZBY4
Molecular weight:: 39382.0

Enzyme Details

6. Fructose-bisphosphate aldolase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: ALDOB
Uniprot ID:: A5PK73
Molecular weight:: 39527.0

Enzyme Details

7. Fructose-bisphosphate aldolase B

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: ALDOB
Uniprot ID:: Q3T0S5
Molecular weight:: 39543.0

Reactions

Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehyde	details

Enzyme Details

8. Triosephosphate isomerase

General function:: Carbohydrate transport and metabolism
Specific function:: Triosephosphate isomerase is an extremely efficient metabolic enzyme that catalyzes the interconversion between dihydroxyacetone phosphate (DHAP) and D-glyceraldehyde-3-phosphate (G3P) in glycolysis and gluconeogenesis.
Gene Name:: TPI1
Uniprot ID:: Q5E956
Molecular weight:: 26690.0

Reactions

Dihydroxyacetone phosphate → D-Glyceraldehyde 3-phosphate	details

Enzyme Details

9. D-2-hydroxyglutarate dehydrogenase, mitochondrial

General function:: Energy production and conversion
Specific function:: Catalyzes the oxidation of D-2-hydroxyglutarate to alpha-ketoglutarate.
Gene Name:: D2HGDH
Uniprot ID:: Q1JPD3
Molecular weight:: 59056.0

Reactions

Eicosanoyl-CoA + Dihydroxyacetone phosphate → DHAP(18:0) + Coenzyme A	details

Enzyme Details

10. Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic

General function:: Energy production and conversion
Specific function:: Not Available
Gene Name:: GPD1
Uniprot ID:: Q5EA88
Molecular weight:: 37648.0

Reactions

Dihydroxyacetone phosphate + NADH → Glycerol 3-phosphate + NAD	details
Glycerol 3-phosphate + NAD → Dihydroxyacetone phosphate + NADH	details

Showing metabocard for Dihydroxyacetone phosphate (BMDB0001473)

Structure for BMDB0001473 (Dihydroxyacetone phosphate)

Enzymes

Reactions

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