You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameN-[2-(1,3-BENZODIOXOL-5-YL)ETHYL]-1-[2-(1H-IMIDAZOL-1-YL)-6-METHYLPYRIMIDIN-4-YL]-D-PROLINAMIDE
Accession NumberDB06916
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 420.4644
Monoisotopic: 420.190988664
Chemical FormulaC22H24N6O3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • Phenethylamine
  • Benzodioxole
  • Dialkylarylamine
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • Aminopyrimidine
  • Imidolactam
  • Benzenoid
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Pyrrolidine
  • Imidazole
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid amide
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-n...
Gene Name:
NOS2
Uniprot ID:
P35228
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 ]
Comments
comments powered by Disqus
Drug created on September 15, 2010 15:17 / Updated on August 17, 2016 12:24