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

Identification

Name
N-[2-(1,3-BENZODIOXOL-5-YL)ETHYL]-1-[2-(1H-IMIDAZOL-1-YL)-6-METHYLPYRIMIDIN-4-YL]-D-PROLINAMIDE
Accession Number
DB06916
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 420.4644
Monoisotopic: 420.190988664
Chemical Formula
C22H24N6O3
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][[email protected]@]1(CCCN1C1=NC(=NC(C)=C1)N1C=CN=C1)C(=O)NCCC1=CC2=C(OCO2)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, inducibleNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
16115747
PubChem Substance
99443387
ChemSpider
17273022
BindingDB
50205947
ChEMBL
CHEMBL376632
HET
228
PDB Entries
2oro

Clinical Trials

Clinical Trials
Not Available

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
logP2.1ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.84ChemAxon
pKa (Strongest Basic)6.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area94.4 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity125.17 m3·mol-1ChemAxon
Polarizability44.64 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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
show 7 more
Substituents
Proline or derivatives / Alpha-amino acid amide / Benzodioxole / Dialkylarylamine / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Aminopyrimidine / N-substituted imidazole / Pyrimidine / Imidolactam
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:17 / Updated on December 01, 2017 15:43