Dihydroxyacetone phosphate
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Identification
- Generic Name
- Dihydroxyacetone phosphate
- DrugBank Accession Number
- DB04326
- Background
Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis. Dihydroxyacetone phosphate has been investigated for the treatment of Lymphoma, Large-Cell, Diffuse.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 170.0578
Monoisotopic: 169.998024468 - Chemical Formula
- C3H7O6P
- Synonyms
- 1-hydroxy-3-(phosphonooxy)-2-Propanone
- 1-Hydroxy-3-(phosphonooxy)acetone
- 1,3-Dihydroxy-2-propanone monodihydrogen phosphate
- 1,3-Dihydroxy-2-propanone phosphate
- 1,3-Dihydroxyacetone 1-phosphate
- 3-hydroxy-2-oxopropyl phosphate
- DHAP
- Dihydroxyacetone monophosphate
- Glycerone monophosphate
- Glycerone phosphate
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UFructose-bisphosphate aldolase A Not Available Humans UTriosephosphate isomerase Not Available Humans UFructose-bisphosphate aldolase B Not Available Humans UL-fuculose phosphate aldolase Not Available Escherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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
- Glycerone phosphates / Monoalkyl phosphates / Alpha-hydroxy ketones / Primary alcohols / Organic oxides / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic acyclic compound / Alkyl phosphate / Alpha-hydroxy ketone / Carbonyl group / Glycerone or derivatives / Glycerone phosphate / Hydrocarbon derivative / Ketone / Monoalkyl phosphate
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- glycerone phosphates (CHEBI:16108)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- T7KF2T6W95
- CAS number
- 57-04-5
- InChI Key
- GNGACRATGGDKBX-UHFFFAOYSA-N
- InChI
- InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
- IUPAC Name
- (3-hydroxy-2-oxopropoxy)phosphonic acid
- SMILES
- OCC(=O)COP(O)(O)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001473
- KEGG Compound
- C00111
- PubChem Compound
- 668
- PubChem Substance
- 46507359
- ChemSpider
- 648
- ChEBI
- 16108
- ChEMBL
- CHEMBL1161998
- ZINC
- ZINC000024492326
- PDBe Ligand
- 13P
- Wikipedia
- Dihydroxyacetone_phosphate
- PDB Entries
- 1ado / 1e47 / 1e48 / 1fdj / 1j4e / 1k8y / 1ney / 1nf0 / 1ok4 / 1wpq … show 46 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 21.9 mg/mL ALOGPS 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 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.6635 Blood Brain Barrier + 0.9383 Caco-2 permeable - 0.7358 P-glycoprotein substrate Non-substrate 0.7692 P-glycoprotein inhibitor I Non-inhibitor 0.8116 P-glycoprotein inhibitor II Non-inhibitor 0.8579 Renal organic cation transporter Non-inhibitor 0.9189 CYP450 2C9 substrate Non-substrate 0.86 CYP450 2D6 substrate Non-substrate 0.8518 CYP450 3A4 substrate Non-substrate 0.6864 CYP450 1A2 substrate Non-inhibitor 0.9247 CYP450 2C9 inhibitor Non-inhibitor 0.9077 CYP450 2D6 inhibitor Non-inhibitor 0.9314 CYP450 2C19 inhibitor Non-inhibitor 0.8817 CYP450 3A4 inhibitor Non-inhibitor 0.9496 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9687 Ames test Non AMES toxic 0.7968 Carcinogenicity Non-carcinogens 0.5504 Biodegradation Not ready biodegradable 0.524 Rat acute toxicity 2.2128 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9401 hERG inhibition (predictor II) Non-inhibitor 0.9126
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 132.258178 predictedDarkChem Lite v0.1.0 [M-H]- 133.617578 predictedDarkChem Lite v0.1.0 [M-H]- 134.603478 predictedDarkChem Lite v0.1.0 [M-H]- 133.984278 predictedDarkChem Lite v0.1.0 [M-H]- 120.75467 predictedDeepCCS 1.0 (2019) [M+H]+ 132.962078 predictedDarkChem Lite v0.1.0 [M+H]+ 133.352678 predictedDarkChem Lite v0.1.0 [M+H]+ 134.368378 predictedDarkChem Lite v0.1.0 [M+H]+ 133.383778 predictedDarkChem Lite v0.1.0 [M+H]+ 123.915474 predictedDeepCCS 1.0 (2019) [M+Na]+ 132.386378 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.308378 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.745178 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.424078 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.6689 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsFructose-bisphosphate aldolase A
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Tubulin binding
- 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
- Uniprot Name
- Fructose-bisphosphate aldolase A
- Molecular Weight
- 39419.675 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
2. DetailsTriosephosphate isomerase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Not Available
- Gene Name
- TPI1
- Uniprot ID
- P60174
- Uniprot Name
- Triosephosphate isomerase
- Molecular Weight
- 30790.785 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
3. DetailsFructose-bisphosphate aldolase B
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Phosphatidylcholine binding
- Specific Function
- Not Available
- Gene Name
- ALDOB
- Uniprot ID
- P05062
- Uniprot Name
- Fructose-bisphosphate aldolase B
- Molecular Weight
- 39472.715 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
4. DetailsL-fuculose phosphate aldolase
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Catalyzes the cleavage of L-fuculose 1-phosphate to glycerone phosphate and L-lactaldehyde.
- Gene Name
- fucA
- Uniprot ID
- P0AB87
- Uniprot Name
- L-fuculose phosphate aldolase
- Molecular Weight
- 23775.11 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52