Cannabis Compound Database: Showing Compound Card for Dihydroxyacetone phosphate (CDB004916)

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Record Information

Version

1.0

Created at

2020-04-17 18:50:10 UTC

Updated at

2020-11-18 16:39:00 UTC

CannabisDB ID

CDB004916

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Dihydroxyacetone phosphate

Description

Dihydroxyacetone 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-. Dihydroxyacetone phosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

170.06

Monoisotopic Molecular Weight

169.998

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Subcellular:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Dihydroxyacetone phosphate, 1 MEOX; 3 TMS, GC-MS Spectrum	splash10-0uy4-3954100000-ab5b096e0eac9831cf42	Spectrum
GC-MS	Dihydroxyacetone phosphate, 1 MEOX; 3 TMS, GC-MS Spectrum	splash10-0g0m-3964100000-cd938c4cea382029ce88	Spectrum
GC-MS	Dihydroxyacetone phosphate, non-derivatized, GC-MS Spectrum	splash10-0uy4-3954100000-ab5b096e0eac9831cf42	Spectrum
GC-MS	Dihydroxyacetone phosphate, non-derivatized, GC-MS Spectrum	splash10-0g0m-3964100000-cd938c4cea382029ce88	Spectrum
Predicted GC-MS	Dihydroxyacetone phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01ot-9400000000-a02e9df63512a60b9324	Spectrum
Predicted GC-MS	Dihydroxyacetone phosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9200000000-79dfc0ac375f4d056dc9	Spectrum
Predicted GC-MS	Dihydroxyacetone phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kb-9600000000-050f206e1fed5aaa8c1f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9100000000-c7eb3c008e10f8e15386	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-0f8d50d1d029df4e6c43	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-7c2d8125a273e3fae4f6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-517dcdb0a35f00b4b491	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9000000000-b8d3aeb9415528f3d035	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0udi-2900000000-6091e72aad27af4c7971	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-00fr-0900000000-b948afb7a993bfbaf1df	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-7900000000-fec8dd084ee59efa2286	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kmi-9800000000-beb639c3fffc815897cc	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9000000000-580658c1ae323fa4f718	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016r-6900000000-4a0e75761c8eb8071d1e	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-7e5e1e00ef8f891ffe3e	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-08f155d8875692abc94b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-7900000000-fec8dd084ee59efa2286	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kmi-9800000000-beb639c3fffc815897cc	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9000000000-580658c1ae323fa4f718	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016r-6900000000-4a0e75761c8eb8071d1e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-7e5e1e00ef8f891ffe3e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-08f155d8875692abc94b	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9100000000-83b3c3bba9003d67c444	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fdk-9800000000-dad61e875fa6524224d8	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-007k-9200000000-3ce8b7e1264e4e13f792	2021-09-25	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Fructose and Mannose Degradation
Glycerol Phosphate Shuttle		Not Available
Mitochondrial Electron Transport Chain
Phospholipid Biosynthesis
Glycerolipid Metabolism

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alkaline phosphatase, placental type	ALPP	2q37	P05187	details
Intestinal-type alkaline phosphatase	ALPI	2q37.1	P09923	details
Alkaline phosphatase, tissue-nonspecific isozyme	ALPL	1p36.12	P05186	details
Alkaline phosphatase, placental-like	ALPPL2	2q37	P10696	details
Glycerol-3-phosphate dehydrogenase, mitochondrial	GPD2	2q24.1	P43304	details
Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic	GPD1	12q12-q13	P21695	details
Fructose-bisphosphate aldolase A	ALDOA	16p11.2	P04075	details
Fructose-bisphosphate aldolase C	ALDOC	17cen-q12	P09972	details
Fructose-bisphosphate aldolase B	ALDOB	9q21.3-q22.2	P05062	details
Dihydroxyacetone phosphate acyltransferase	GNPAT	1q42	O15228	details
Triosephosphate isomerase	TPI1	12p13	P60174	details
Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)	DAK	11q12.2	Q3LXA3	details
Glycerol-3-phosphate dehydrogenase 1-like protein	GPD1L	3p22.3	Q8N335	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Glycerol-3-phosphate dehydrogenase 1-like protein	GPD1L	3p22.3	Q8N335	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alkaline phosphatase, placental type	ALPP	2q37	P05187	details
Intestinal-type alkaline phosphatase	ALPI	2q37.1	P09923	details
Alkaline phosphatase, tissue-nonspecific isozyme	ALPL	1p36.12	P05186	details
Alkaline phosphatase, placental-like	ALPPL2	2q37	P10696	details
Glycerol-3-phosphate dehydrogenase, mitochondrial	GPD2	2q24.1	P43304	details
Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)	DAK	11q12.2	Q3LXA3	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001473

DrugBank ID

DB04326

Phenol Explorer Compound ID

Not Available

FoodDB 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

General References

Not Available

Only showing the first 10 proteins. There are 20 proteins in total.

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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

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

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

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

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

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

Transporters

Enzyme Details

1. Glycerol-3-phosphate dehydrogenase 1-like protein

General function:: Involved in oxidoreductase activity
Specific function:: Plays a role in regulating cardiac sodium current; decreased enzymatic activity with resulting increased levels of glycerol 3-phosphate activating the DPD1L-dependent SCN5A phosphorylation pathway, may ultimately lead to decreased sodium current; cardiac sodium current may also be reduced due to alterations of NAD(H) balance induced by DPD1L.
Gene Name:: GPD1L
Uniprot ID:: Q8N335
Molecular weight:: 38418.44

Only showing the first 10 proteins. There are 20 proteins in total.

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Showing Compound Card for Dihydroxyacetone phosphate (CDB004916)

Structure for CDB004916 (Dihydroxyacetone phosphate)

Enzymes

Transporters