NAV

2-(Beta-D-Glucopyranosyl)-5-Methyl-1,2,3-Benzimidazole

Identification

Generic Name
2-(Beta-D-Glucopyranosyl)-5-Methyl-1,2,3-Benzimidazole
DrugBank Accession Number
DB03133
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 294.3031
Monoisotopic: 294.121571696
Chemical Formula
C14H18N2O5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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
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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 2-pyranosylbenzimidazoles. These are nucleoside and nucleotide analogs with a structure that consists of a benzimidazole which is N-substituted at the 2-position with a pyranose moiety. Nucleotide analogues contain a phosphate group linked to the C5 carbon atom of the pyranose.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Nucleoside and nucleotide analogues
Sub Class
2-pyranosylbenzimidazoles
Direct Parent
2-pyranosylbenzimidazoles
Alternative Parents
C-glycosyl compounds / Benzimidazoles / Oxanes / Monosaccharides / Benzenoids / Imidazoles / Heteroaromatic compounds / Secondary alcohols / 1,2-diols / Oxacyclic compounds
show 5 more
Substituents
1,2-diol / 2-pyranosylbenzimidazole / Alcohol / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / C-glycosyl compound / Dialkyl ether
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
XIJZORUYQZBFJK-UJPOAAIJSA-N
InChI
InChI=1S/C14H18N2O5/c1-6-2-3-7-8(4-6)16-14(15-7)13-12(20)11(19)10(18)9(5-17)21-13/h2-4,9-13,17-20H,5H2,1H3,(H,15,16)/t9-,10-,11+,12-,13-/m1/s1
IUPAC Name
(2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-(6-methyl-1H-1,3-benzodiazol-2-yl)oxane-3,4,5-triol
SMILES
[H][C@]1(CO)O[C@@]([H])(C2=NC3=C(N2)C=C(C)C=C3)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

References

General References
Not Available
PubChem Compound
49867153
PubChem Substance
46508048
ChemSpider
23106964
ZINC
ZINC000038378584
PDBe Ligand
IMK
PDB Entries
1xkx

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 Solubility20.4 mg/mLALOGPS
logP-0.38ALOGPS
logP-0.76Chemaxon
logS-1.2ALOGPS
pKa (Strongest Acidic)11.23Chemaxon
pKa (Strongest Basic)4.85Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area118.83 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity72.53 m3·mol-1Chemaxon
Polarizability29.76 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9895
Blood Brain Barrier+0.5914
Caco-2 permeable-0.7833
P-glycoprotein substrateSubstrate0.6185
P-glycoprotein inhibitor INon-inhibitor0.9495
P-glycoprotein inhibitor IINon-inhibitor0.9656
Renal organic cation transporterNon-inhibitor0.8877
CYP450 2C9 substrateNon-substrate0.7643
CYP450 2D6 substrateNon-substrate0.7806
CYP450 3A4 substrateNon-substrate0.6204
CYP450 1A2 substrateNon-inhibitor0.5
CYP450 2C9 inhibitorNon-inhibitor0.9159
CYP450 2D6 inhibitorNon-inhibitor0.9256
CYP450 2C19 inhibitorNon-inhibitor0.8642
CYP450 3A4 inhibitorNon-inhibitor0.9496
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7883
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.9528
BiodegradationNot ready biodegradable0.9772
Rat acute toxicity2.3359 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9453
hERG inhibition (predictor II)Non-inhibitor0.8625
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-ba91b05998d563391837
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0190000000-5c850918dfdf651fa482
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0940000000-440a105ff29c4fbe1d72
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-06si-0930000000-35391b63a2bfb0c700fa
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-8920000000-d1e2ffadefa7b1df9dec
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0910000000-3e768548617a187b8f6e
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]-170.37566
predicted
DeepCCS 1.0 (2019)
[M+H]+172.77122
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.4991
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Glycogen phosphorylase, muscle form
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 at June 13, 2005 13:24 / Updated at June 12, 2020 16:52