NAV

N-[2-(1,3-BENZODIOXOL-5-YL)ETHYL]-1-[2-(1H-IMIDAZOL-1-YL)-6-METHYLPYRIMIDIN-4-YL]-D-PROLINAMIDE

Identification

Generic Name
N-[2-(1,3-BENZODIOXOL-5-YL)ETHYL]-1-[2-(1H-IMIDAZOL-1-YL)-6-METHYLPYRIMIDIN-4-YL]-D-PROLINAMIDE
DrugBank Accession Number
DB06916
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 420.4644
Monoisotopic: 420.190988664
Chemical Formula
C22H24N6O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, inducibleNot 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 proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Proline and derivatives
Alternative Parents
Alpha amino acid amides / Benzodioxoles / Pyrrolidinecarboxamides / Dialkylarylamines / Aminopyrimidines and derivatives / Benzenoids / N-substituted imidazoles / Imidolactams / Heteroaromatic compounds / Secondary carboxylic acid amides
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Substituents
Acetal / Alpha-amino acid amide / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzodioxole / Carbonyl group / Carboxamide group
show 20 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
LBCGUKCXRVUULK-QGZVFWFLSA-N
InChI
InChI=1S/C22H24N6O3/c1-15-11-20(26-22(25-15)27-10-8-23-13-27)28-9-2-3-17(28)21(29)24-7-6-16-4-5-18-19(12-16)31-14-30-18/h4-5,8,10-13,17H,2-3,6-7,9,14H2,1H3,(H,24,29)/t17-/m1/s1
IUPAC Name
(2R)-N-[2-(2H-1,3-benzodioxol-5-yl)ethyl]-1-[2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl]pyrrolidine-2-carboxamide
SMILES
[H][C@@]1(CCCN1C1=NC(=NC(C)=C1)N1C=CN=C1)C(=O)NCCC1=CC2=C(OCO2)C=C1

References

General References
Not Available
PubChem Compound
16115747
PubChem Substance
99443387
ChemSpider
17273022
BindingDB
50205947
ChEMBL
CHEMBL376632
ZINC
ZINC000034951255
PDBe Ligand
228
PDB Entries
2oro

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 Solubility0.321 mg/mLALOGPS
logP2.24ALOGPS
logP2.47Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.8Chemaxon
pKa (Strongest Basic)5.64Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area94.4 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity125.17 m3·mol-1Chemaxon
Polarizability44.69 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8424
Caco-2 permeable-0.5611
P-glycoprotein substrateSubstrate0.6188
P-glycoprotein inhibitor IInhibitor0.7187
P-glycoprotein inhibitor IINon-inhibitor0.5782
Renal organic cation transporterNon-inhibitor0.729
CYP450 2C9 substrateNon-substrate0.8458
CYP450 2D6 substrateNon-substrate0.7655
CYP450 3A4 substrateSubstrate0.5895
CYP450 1A2 substrateInhibitor0.8569
CYP450 2C9 inhibitorNon-inhibitor0.8032
CYP450 2D6 inhibitorInhibitor0.765
CYP450 2C19 inhibitorInhibitor0.5317
CYP450 3A4 inhibitorInhibitor0.8826
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9093
Ames testNon AMES toxic0.5657
CarcinogenicityNon-carcinogens0.844
BiodegradationNot ready biodegradable0.8524
Rat acute toxicity2.4056 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8608
hERG inhibition (predictor II)Inhibitor0.5247
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/MSsplash10-00di-0000900000-8a5a34e3c43246e8574e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gb9-2092500000-280f97cee75f7304f7a8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dm-0615900000-28aadd9b9b32315653c3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-106r-1494400000-12c821d166e3839ae603
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-0963300000-8f2dac604d0f2b644128
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9444100000-c708c14dbd4bd467aaae
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]-193.25322
predicted
DeepCCS 1.0 (2019)
[M+H]+195.64879
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.57777
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Nitric oxide synthase, inducible
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity ...
Gene Name
NOS2
Uniprot ID
P35228
Uniprot Name
Nitric oxide synthase, inducible
Molecular Weight
131116.3 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 21:17 / Updated at June 12, 2020 16:52