Duvoglustat

Identification

Name
Duvoglustat
Accession Number
DB03206  (EXPT01227, EXPT02374, EXPT01236)
Type
Small Molecule
Groups
Experimental
Description

An alpha-glucosidase inhibitor with antiviral action. Derivatives of deoxynojirimycin may have anti-HIV activity.

Structure
Thumb
Synonyms
  • 1 deoxynojirimycin
  • 1-deoxy-nojirimycin
  • 1-deoxynojirimycin
  • 1,5-deoxy-1,5-imino-D-mannitol
  • 1,5-dideoxy-1,5-imino-D-glucitol
  • 5-amino-1,5-dideoxy-D-glucopyranose
  • D-1-deoxynojirimycin
  • Deoxynojirimycin
  • DNJ
External IDs
BAY-H-5595
Categories
UNII
FZ56898FLE
CAS number
19130-96-2
Weight
Average: 163.1717
Monoisotopic: 163.084457909
Chemical Formula
C6H13NO4
InChI Key
LXBIFEVIBLOUGU-JGWLITMVSA-N
InChI
InChI=1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/t3-,4+,5-,6-/m1/s1
IUPAC Name
(2R,3R,4R,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCyclomaltodextrin glucanotransferaseNot AvailableBacillus sp. (strain 1011)
UBeta-glucosidase ANot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UEndoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidaseNot AvailableHuman
UMannosyl-oligosaccharide alpha-1,2-mannosidaseNot AvailablePenicillium citrinum
UXylose isomeraseNot AvailableArthrobacter sp. (strain NRRL B3728)
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

ORL-RAT LD50: > 5g/kg.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Theo Schroder, Mathias Stubbe, "Process for preparing 1-deoxynojirimycin and N-derivatives thereof." U.S. Patent US4806650, issued September, 1986.

US4806650
General References
Not Available
External Links
KEGG Drug
D09605
KEGG Compound
C16843
PubChem Compound
29435
PubChem Substance
46507744
ChemSpider
27360
BindingDB
18351
ChEBI
44369
ChEMBL
CHEMBL307429
HET
NOJ
Wikipedia
1-Deoxynojirimycin
PDB Entries
1die / 1dog / 1i75 / 1oim / 2j77 / 2jke / 2pwd / 2x2j / 2xg9 / 2ya2
show 13 more
MSDS
Download (84.8 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP-1.80SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility511.0 mg/mLALOGPS
logP-2.2ALOGPS
logP-2.9ChemAxon
logS0.5ALOGPS
pKa (Strongest Acidic)12.91ChemAxon
pKa (Strongest Basic)8.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area92.95 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.57 m3·mol-1ChemAxon
Polarizability15.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6137
Blood Brain Barrier-0.8982
Caco-2 permeable-0.8093
P-glycoprotein substrateSubstrate0.5892
P-glycoprotein inhibitor INon-inhibitor0.9255
P-glycoprotein inhibitor IINon-inhibitor0.9514
Renal organic cation transporterNon-inhibitor0.8207
CYP450 2C9 substrateNon-substrate0.8718
CYP450 2D6 substrateNon-substrate0.8056
CYP450 3A4 substrateNon-substrate0.7092
CYP450 1A2 substrateNon-inhibitor0.9401
CYP450 2C9 inhibitorNon-inhibitor0.9543
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9671
CYP450 3A4 inhibitorNon-inhibitor0.9886
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9896
Ames testNon AMES toxic0.8765
CarcinogenicityNon-carcinogens0.9653
BiodegradationNot ready biodegradable0.7247
Rat acute toxicity1.5447 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8879
hERG inhibition (predictor II)Non-inhibitor0.9253
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Not Available
Direct Parent
Piperidines
Alternative Parents
Secondary alcohols / 1,2-aminoalcohols / Polyols / Dialkylamines / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Piperidine / 1,2-aminoalcohol / Secondary alcohol / Secondary aliphatic amine / Polyol / Secondary amine / Azacycle / Primary alcohol / Alcohol / Organic oxygen compound
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
2-(hydroxymethyl)piperidine-3,4,5-triol (CHEBI:44369)

Targets

Kind
Protein
Organism
Bacillus sp. (strain 1011)
Pharmacological action
Unknown
General Function
Starch binding
Specific Function
Not Available
Gene Name
cgt
Uniprot ID
P05618
Uniprot Name
Cyclomaltodextrin glucanotransferase
Molecular Weight
78340.03 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]
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Beta-glucosidase activity
Specific Function
Not Available
Gene Name
bglA
Uniprot ID
Q08638
Uniprot Name
Beta-glucosidase A
Molecular Weight
51548.055 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Mannosyl-oligosaccharide 1,2-alpha-mannosidase activity
Specific Function
Involved in glycoprotein quality control targeting of misfolded glycoproteins for degradation. It primarily trims a single alpha-1,2-linked mannose residue from Man(9)GlcNAc(2) to produce Man(8)Glc...
Gene Name
MAN1B1
Uniprot ID
Q9UKM7
Uniprot Name
Endoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase
Molecular Weight
79579.18 Da
References
  1. 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
Penicillium citrinum
Pharmacological action
Unknown
General Function
Mannosyl-oligosaccharide 1,2-alpha-mannosidase activity
Specific Function
Involved in the maturation of Asn-linked oligosaccharides. Progressively trim alpha-1,2-linked mannose residues from Man(9)GlcNAc(2) to produce Man(5)GlcNAc(2).
Gene Name
MSDC
Uniprot ID
P31723
Uniprot Name
Mannosyl-oligosaccharide alpha-1,2-mannosidase
Molecular Weight
56569.37 Da
Kind
Protein
Organism
Arthrobacter sp. (strain NRRL B3728)
Pharmacological action
Unknown
General Function
Xylose isomerase activity
Specific Function
Not Available
Gene Name
xylA
Uniprot ID
P12070
Uniprot Name
Xylose isomerase
Molecular Weight
43291.15 Da
References
  1. Collyer CA, Blow DM: Observations of reaction intermediates and the mechanism of aldose-ketose interconversion by D-xylose isomerase. Proc Natl Acad Sci U S A. 1990 Feb;87(4):1362-6. [PubMed:2304904]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:09