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Kifunensine

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Overview

Structure
DrugBank ID
DB02742
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
Kifunensine
DrugBank Accession Number
DB02742
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 232.1907
Monoisotopic: 232.069536126
Chemical Formula
C8H12N2O6
Synonyms
Not Available
External IDs
  • FR-900494
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAlpha-mannosidase 2Not AvailableHumans
UEndoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidaseNot AvailableHumans
UMannosyl-oligosaccharide alpha-1,2-mannosidaseNot AvailablePenicillium citrinum
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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Imidazopyridines / Piperidines / Imidazolidinones / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Secondary alcohols / Lactams / Polyols / Azacyclic compounds / Primary alcohols
show 5 more
Substituents
Alcohol / Aliphatic heteropolycyclic compound / Alpha-amino acid or derivatives / Azacycle / Carbonyl group / Carboxamide group / Hydrocarbon derivative / Imidazolidine / Imidazolidinone / Imidazopyridine
show 14 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
0NI8960271
CAS number
109944-15-2
InChI Key
OIURYJWYVIAOCW-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)-octahydroimidazo[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

References

Synthesis Reference

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

US20040063973
General References
Not Available
PubChem Compound
130611
PubChem Substance
46505714
ChemSpider
115533
ChEMBL
CHEMBL1233851
ZINC
ZINC000003795857
PDBe Ligand
KIF
Wikipedia
Kifunensine
PDB Entries
1fo3 / 1krf / 1ps3 / 2wvz / 5ne5

Clinical Trials

Clinical Trials
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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 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 FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0fk9-9660000000-7162eae2a7a064b03a1f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-af4c3af397f9f33bda80
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0190000000-11047fd21287b1c117d1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-003r-0590000000-9c07e9c6f74262538e8d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ugl-4950000000-781ed929864a9c6a0bed
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fba-3910000000-4de7e1c56c2c5b29fa7e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ffx-8910000000-9f071c5c460974ce0fe9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-147.92577
predicted
DeepCCS 1.0 (2019)
[M+H]+150.25822
predicted
DeepCCS 1.0 (2019)
[M+Na]+157.08049
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Alpha-mannosidase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General 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
Specific Function
alpha-mannosidase activity
Gene Name
MAN2A1
Uniprot ID
Q16706
Uniprot Name
Alpha-mannosidase 2
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. [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]
Details2. Endoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General 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)
Specific Function
calcium ion binding
Gene Name
MAN1B1
Uniprot ID
Q9UKM7
Uniprot Name
Endoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase
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. [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]
Details3. Mannosyl-oligosaccharide alpha-1,2-mannosidase
Kind
Protein
Organism
Penicillium citrinum
Pharmacological action
Unknown
General 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).
Specific Function
calcium ion binding
Gene Name
MSDC
Uniprot ID
P31723
Uniprot Name
Mannosyl-oligosaccharide alpha-1,2-mannosidase
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. [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]

Drug created at June 13, 2005 13:24 / Updated at August 02, 2020 07:59