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Identification
NameDuvoglustat
Accession NumberDB03206  (EXPT01227, EXPT02374, EXPT01236)
TypeSmall Molecule
GroupsExperimental
DescriptionAn alpha-glucosidase inhibitor with antiviral action. Derivatives of deoxynojirimycin may have anti-HIV activity. [PubChem]
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
1,5-dideoxy-1,5-imino-D-glucitol
5-amino-1,5-dideoxy-D-glucopyranose
D-1-deoxynojirimycin
Deoxynojirimycin
DNJ
External Identifiers
  • BAY-H-5595
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIFZ56898FLE
CAS number19130-96-2
WeightAverage: 163.1717
Monoisotopic: 163.084457909
Chemical FormulaC6H13NO4
InChI KeyLXBIFEVIBLOUGU-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
[H][C@]1(O)CN[C@]([H])(CO)[C@@]([H])(O)[C@]1([H])O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Cyclomaltodextrin glucanotransferaseProteinunknownNot AvailableBacillus sp. (strain 1011)P05618 details
Beta-glucosidase AProteinunknownNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)Q08638 details
Endoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidaseProteinunknownNot AvailableHumanQ9UKM7 details
Mannosyl-oligosaccharide alpha-1,2-mannosidaseProteinunknownNot AvailablePenicillium citrinumP31723 details
Xylose isomeraseProteinunknownNot AvailableArthrobacter sp. (strain NRRL B3728)P12070 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityORL-RAT LD50: > 5g/kg.
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (84.8 KB)
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassNot Available
Direct ParentPiperidines
Alternative Parents
Substituents
  • Piperidine
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors

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
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
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)GlcNAc(2), but at high enzyme concentrations, as found in the ER quality control compartment (ERQC), it further trims the carbohydrates to Man(5-6)GlcNAc(2).
Gene Name:
MAN1B1
Uniprot ID:
Q9UKM7
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
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23