Dihydroxyacetone phosphate

Identification

Name
Dihydroxyacetone phosphate
Accession Number
DB04326  (EXPT00026, DB12496)
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
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
Categories
UNII
T7KF2T6W95
CAS number
57-04-5
Weight
Average: 170.0578
Monoisotopic: 169.998024468
Chemical Formula
C3H7O6P
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UFructose-bisphosphate aldolase ANot AvailableHuman
UTriosephosphate isomeraseNot AvailableHuman
UFructose-bisphosphate aldolase BNot AvailableHuman
UL-fuculose phosphate aldolaseNot AvailableEscherichia 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Glycerol Kinase DeficiencyDisease
D-Glyceric AciduraDisease
Warburg EffectMetabolic
Fructose Intolerance, HereditaryDisease
Gluconeogenesis from L-Malic AcidMetabolic
Fructose MetabolismMetabolic
Phospholipid BiosynthesisMetabolic
Phospholipid Biosynthesis CL(14:0/16:1(9Z)/19:0cycv8c/14:0)Metabolic
Phospholipid Biosynthesis CL(14:0/18:1(9Z)/14:0/14:0)Metabolic
Phospholipid Biosynthesis CL(14:0/18:1(9Z)/14:0/18:1(9Z))Metabolic
Phospholipid Biosynthesis CL(14:0/18:1(9Z)/19:0cycv8c/14:0)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/14:0/14:0/17:0cycw7c)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/15:0cyclo/16:0/17:0cycw7c)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/16:1(9Z))Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/15:0cyclo/17:0cycw7c/18:1(9Z))Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/16:1(9Z))Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/17:0cycw7c)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/15:0cyclo/19:0cycv8c/14:0)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/15:0cyclo/19:0cycv8c/15:0cyclo)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/16:0/16:0/16:1(9Z))Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/16:0/16:0/19:0cycv8c)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/16:0/16:1(9Z)/16:0)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/16:0/16:1(9Z)/15:0cyclo)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/16:0/17:0cycw7c/17:0cycw7c)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/16:1(9Z)/16:1(9Z)/16:0)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/16:1(9Z)/17:0cycw7c/16:1(9Z))Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/16:1(9Z)/18:1(9Z)/16:1(9Z))Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/17:0cycw7c/15:0cyclo/17:0cycw7c)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/17:0cycw7c/16:0/17:0cycw7c)Metabolic
Phospholipid Biosynthesis CL(15:0cyclo/17:0cycw7c/17:0cycw7c/17:0cycw7c)Metabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
HET
13P
Wikipedia
Dihydroxyacetone_phosphate
PDB Entries
1ado / 1e47 / 1e48 / 1fdj / 1j4e / 1k8y / 1ney / 1nf0 / 1ok4 / 1wpq
show 41 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentLymphoma, Hodgkins / Refractory / Relapses1
1, 2RecruitingTreatmentLymphoma, Hodgkins1
1, 2Unknown StatusTreatmentNon-Hodgkin's Lymphoma (NHL)1
2Active Not RecruitingTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)1
2CompletedSupportive CareMalignant Lymphomas1
2CompletedTreatmentAdult T-cell lymphomas/leukaemias1
2CompletedTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)1
2CompletedTreatmentLymphoma, Large-Cell, Diffuse1
3CompletedTreatmentLymphoma, Large-Cell, Diffuse1
3CompletedTreatmentPlasmodium Infections1
3RecruitingTreatmentMantle Cell Lymphoma (MCL)1
Not AvailableRecruitingTreatmentPlasmodium Infections1

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
PropertyValueSource
Water Solubility21.9 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.47 m3·mol-1ChemAxon
Polarizability12.64 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6635
Blood Brain Barrier+0.9383
Caco-2 permeable-0.7358
P-glycoprotein substrateNon-substrate0.7692
P-glycoprotein inhibitor INon-inhibitor0.8116
P-glycoprotein inhibitor IINon-inhibitor0.8579
Renal organic cation transporterNon-inhibitor0.9189
CYP450 2C9 substrateNon-substrate0.86
CYP450 2D6 substrateNon-substrate0.8518
CYP450 3A4 substrateNon-substrate0.6864
CYP450 1A2 substrateNon-inhibitor0.9247
CYP450 2C9 inhibitorNon-inhibitor0.9077
CYP450 2D6 inhibitorNon-inhibitor0.9314
CYP450 2C19 inhibitorNon-inhibitor0.8817
CYP450 3A4 inhibitorNon-inhibitor0.9496
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9687
Ames testNon AMES toxic0.7968
CarcinogenicityNon-carcinogens0.5504
BiodegradationNot ready biodegradable0.524
Rat acute toxicity2.2128 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9401
hERG inhibition (predictor II)Non-inhibitor0.9126
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-0uy4-3954100000-ab5b096e0eac9831cf42
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-0g0m-3964100000-cd938c4cea382029ce88
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-0uy4-3954100000-ab5b096e0eac9831cf42
GC-MS Spectrum - GC-MSGC-MSsplash10-0g0m-3964100000-cd938c4cea382029ce88
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-7900000000-fec8dd084ee59efa2286
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kmi-9800000000-beb639c3fffc815897cc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4j-9000000000-580658c1ae323fa4f718
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-016r-6900000000-4a0e75761c8eb8071d1e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9100000000-7e5e1e00ef8f891ffe3e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-08f155d8875692abc94b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-7900000000-fec8dd084ee59efa2286
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kmi-9800000000-beb639c3fffc815897cc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4j-9000000000-580658c1ae323fa4f718
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-016r-6900000000-4a0e75761c8eb8071d1e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9100000000-7e5e1e00ef8f891ffe3e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-08f155d8875692abc94b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00kb-9600000000-050f206e1fed5aaa8c1f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-9100000000-c7eb3c008e10f8e15386
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-0f8d50d1d029df4e6c43
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-7c2d8125a273e3fae4f6
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-517dcdb0a35f00b4b491
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-9000000000-b8d3aeb9415528f3d035

Taxonomy

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
Glycerone phosphate / Monosaccharide phosphate / Monoalkyl phosphate / Alkyl phosphate / Glycerone or derivatives / Phosphoric acid ester / Organic phosphoric acid derivative / Alpha-hydroxy ketone / Ketone / Organic oxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
glycerone phosphates (CHEBI:16108)

Targets

Kind
Protein
Organism
Human
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
  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]
Kind
Protein
Organism
Human
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
  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]
Kind
Protein
Organism
Human
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
  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]
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
  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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:55