NAV

(2R,3R)-7-(methylsulfonyl)-3-(2,4,5-trifluorophenyl)-1,2,3,4-tetrahydropyrido[1,2-a]benzimidazol-2-amine

Identification

Generic Name
(2R,3R)-7-(methylsulfonyl)-3-(2,4,5-trifluorophenyl)-1,2,3,4-tetrahydropyrido[1,2-a]benzimidazol-2-amine
DrugBank Accession Number
DB07193
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 395.399
Monoisotopic: 395.091532076
Chemical Formula
C18H16F3N3O2S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDipeptidyl peptidase 4Not 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 benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Not Available
Direct Parent
Benzimidazoles
Alternative Parents
Fluorobenzenes / Aralkylamines / N-substituted imidazoles / Aryl fluorides / Sulfones / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organofluorides / Organic oxides
show 2 more
Substituents
Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzenoid / Benzimidazole / Fluorobenzene
show 18 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
HJJAYSSCWGUPKO-ABAIWWIYSA-N
InChI
InChI=1S/C18H16F3N3O2S/c1-27(25,26)9-2-3-17-16(4-9)23-18-6-11(15(22)8-24(17)18)10-5-13(20)14(21)7-12(10)19/h2-5,7,11,15H,6,8,22H2,1H3/t11-,15+/m1/s1
IUPAC Name
(11R,12R)-5-methanesulfonyl-11-(2,4,5-trifluorophenyl)-1,8-diazatricyclo[7.4.0.0^{2,7}]trideca-2,4,6,8-tetraen-12-amine
SMILES
[H][C@]1(N)CN2C(C[C@]1([H])C1=C(F)C=C(F)C(F)=C1)=NC1=CC(=CC=C21)S(C)(=O)=O

References

General References
Not Available
PubChem Compound
11710963
PubChem Substance
99443664
ChemSpider
9885685
ChEMBL
CHEMBL1197118
ZINC
ZINC000034635756
PDBe Ligand
677
PDB Entries
3hab

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 Solubility0.0389 mg/mLALOGPS
logP1.8ALOGPS
logP1.86Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)16.17Chemaxon
pKa (Strongest Basic)9.71Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area77.98 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity94.04 m3·mol-1Chemaxon
Polarizability37.98 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9966
Blood Brain Barrier+0.8911
Caco-2 permeable-0.5257
P-glycoprotein substrateSubstrate0.5207
P-glycoprotein inhibitor INon-inhibitor0.8313
P-glycoprotein inhibitor IINon-inhibitor0.9279
Renal organic cation transporterNon-inhibitor0.7164
CYP450 2C9 substrateNon-substrate0.7989
CYP450 2D6 substrateNon-substrate0.7518
CYP450 3A4 substrateSubstrate0.532
CYP450 1A2 substrateInhibitor0.6429
CYP450 2C9 inhibitorNon-inhibitor0.674
CYP450 2D6 inhibitorNon-inhibitor0.8048
CYP450 2C19 inhibitorNon-inhibitor0.5731
CYP450 3A4 inhibitorInhibitor0.6116
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6112
Ames testNon AMES toxic0.586
CarcinogenicityNon-carcinogens0.7481
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6346 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9825
hERG inhibition (predictor II)Inhibitor0.5773
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/MSsplash10-0002-0009000000-0b4974983a4d24a1d5f5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-771c916ff3c7037e1ae3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-dabba2b7c190de2c0cbe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-4d6a7e3d6e82a087b03a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-3593000000-5f9059db51aa4aa6e51e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-022a-0179000000-b6aad415e834e19aaad1
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]-185.7356
predicted
DeepCCS 1.0 (2019)
[M+H]+188.13115
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.04369
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dipeptidyl peptidase 4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation. Acts as a positive regulator of T-cell coactivation, by bindi...
Gene Name
DPP4
Uniprot ID
P27487
Uniprot Name
Dipeptidyl peptidase 4
Molecular Weight
88277.935 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. [Article]

Drug created at September 15, 2010 21:19 / Updated at June 12, 2020 16:52