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Identification
NameKifunensine
Accession NumberDB02742  (EXPT01973)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
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
UNII0NI8960271
CAS number109944-15-2
WeightAverage: 232.1907
Monoisotopic: 232.069536126
Chemical FormulaC8H12N2O6
InChI KeyOIURYJWYVIAOCW-PQMKYFCFSA-N
InChI
InChI=1S/C8H12N2O6/c11-1-2-3(12)4(13)5(14)6-9-7(15)8(16)10(2)6/h2-6,11-14H,1H2,(H,9,15)/t2-,3-,4+,5+,6+/m1/s1
IUPAC Name
(5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-octahydroimidazolidino[1,2-a]pyridine-2,3-dione
SMILES
[H][C@]12NC(=O)C(=O)N1[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@]2([H])O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as imidazopyridines. These are organic polycyclic compounds containing an imidazole ring fused to a pyridine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyridines
Sub ClassNot Available
Direct ParentImidazopyridines
Alternative Parents
Substituents
  • Imidazopyridine
  • Piperidine
  • Imidazolidinone
  • Tertiary carboxylic acid amide
  • Imidazolidine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Lactam
  • Carboxamide group
  • 1,2-diol
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7286
Blood Brain Barrier-0.63
Caco-2 permeable-0.8046
P-glycoprotein substrateNon-substrate0.5167
P-glycoprotein inhibitor INon-inhibitor0.9685
P-glycoprotein inhibitor IINon-inhibitor0.9089
Renal organic cation transporterNon-inhibitor0.8978
CYP450 2C9 substrateNon-substrate0.856
CYP450 2D6 substrateNon-substrate0.8334
CYP450 3A4 substrateNon-substrate0.6218
CYP450 1A2 substrateNon-inhibitor0.8922
CYP450 2C9 inhibitorNon-inhibitor0.9522
CYP450 2D6 inhibitorNon-inhibitor0.9473
CYP450 2C19 inhibitorNon-inhibitor0.9546
CYP450 3A4 inhibitorNon-inhibitor0.9885
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9865
Ames testNon AMES toxic0.7483
CarcinogenicityNon-carcinogens0.9322
BiodegradationNot ready biodegradable0.868
Rat acute toxicity2.0853 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.987
hERG inhibition (predictor II)Non-inhibitor0.9466
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 PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility190.0 mg/mLALOGPS
logP-2.5ALOGPS
logP-3.7ChemAxon
logS-0.09ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area130.33 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.42 m3·mol-1ChemAxon
Polarizability20.32 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Paul Benjes, “Process for preparing kifunensine intermediate and kifunensine therefrom.” U.S. Patent US20040063973, issued April 01, 2004.

US20040063973
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Catalyzes the first committed step in the biosynthesis of complex N-glycans. It controls conversion of high mannose to complex N-glycans; the final hydrolytic step in the N-glycan maturation pathway.
Gene Name:
MAN2A1
Uniprot ID:
Q16706
Molecular Weight:
131139.485 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:
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. 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
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on May 07, 2016 17:28