(3,4,5-Trihydroxy-6-Hydroxymethyl-Tetrahydro-Pyran-2-Yl)-Phosphoramidic Acid Dimethyl Ester

Identification

Generic Name
(3,4,5-Trihydroxy-6-Hydroxymethyl-Tetrahydro-Pyran-2-Yl)-Phosphoramidic Acid Dimethyl Ester
DrugBank Accession Number
DB03392
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 287.2042
Monoisotopic: 287.077003069
Chemical Formula
C8H18NO8P
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlycogen phosphorylase, muscle formNot AvailableHumans
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
Adverseeffects
Improve decision support & research outcomes
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Toxicity

Not Available

Pathways
Not Available
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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Hexoses
Alternative Parents
Phosphoric diester monoamides / Oxanes / Organic phosphoramides / Secondary alcohols / Polyols / Oxacyclic compounds / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 1 more
Substituents
Alcohol / Aliphatic heteromonocyclic compound / Hexose monosaccharide / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic phosphoric acid amide / Organic phosphoric acid derivative / Organoheterocyclic compound / Organonitrogen compound
show 8 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
LJBUJRWZZYUNKX-JAJWTYFOSA-N
InChI
InChI=1S/C8H18NO8P/c1-15-18(14,16-2)9-8-7(13)6(12)5(11)4(3-10)17-8/h4-8,10-13H,3H2,1-2H3,(H,9,14)/t4-,5-,6+,7-,8-/m1/s1
IUPAC Name
(2R,3R,4S,5S,6R)-2-[(dimethoxyphosphoryl)amino]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES
[H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(NP(=O)(OC)OC)[C@]1([H])O

References

General References
Not Available
PubChem Compound
656959
PubChem Substance
46504665
ChemSpider
571197
BindingDB
50363874
ChEMBL
CHEMBL1233057
ZINC
ZINC000016051653
PDBe Ligand
GL6
PDB Entries
1xc7

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility32.6 mg/mLALOGPS
logP-2.3ALOGPS
logP-3ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)12.33ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area137.71 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity57.71 m3·mol-1ChemAxon
Polarizability24.68 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9392
Blood Brain Barrier-0.7729
Caco-2 permeable-0.6602
P-glycoprotein substrateNon-substrate0.7802
P-glycoprotein inhibitor INon-inhibitor0.7095
P-glycoprotein inhibitor IINon-inhibitor0.9493
Renal organic cation transporterNon-inhibitor0.9606
CYP450 2C9 substrateNon-substrate0.7643
CYP450 2D6 substrateNon-substrate0.8137
CYP450 3A4 substrateSubstrate0.5461
CYP450 1A2 substrateNon-inhibitor0.8537
CYP450 2C9 inhibitorNon-inhibitor0.8854
CYP450 2D6 inhibitorNon-inhibitor0.9117
CYP450 2C19 inhibitorNon-inhibitor0.8541
CYP450 3A4 inhibitorNon-inhibitor0.9611
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9592
Ames testNon AMES toxic0.5512
CarcinogenicityNon-carcinogens0.9302
BiodegradationNot ready biodegradable0.7342
Rat acute toxicity2.5043 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9281
hERG inhibition (predictor II)Non-inhibitor0.8882
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
Gene Name
PYGM
Uniprot ID
P11217
Uniprot Name
Glycogen phosphorylase, muscle form
Molecular Weight
97091.265 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. [Article]
  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. [Article]
  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. [Article]

Drug created on June 13, 2005 13:24 / Updated on June 12, 2020 16:52