N-[2-(1,3-BENZODIOXOL-5-YL)ETHYL]-1-[2-(1H-IMIDAZOL-1-YL)-6-METHYLPYRIMIDIN-4-YL]-D-PROLINAMIDE
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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
- Weight
- Average: 420.4644
Monoisotopic: 420.190988664 - Chemical Formula
- C22H24N6O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UNitric oxide synthase, inducible Not Available Humans - 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 show 7 more
- 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
- External Links
- PubChem Compound
- 16115747
- PubChem Substance
- 99443387
- ChemSpider
- 17273022
- BindingDB
- 50205947
- ChEMBL
- CHEMBL376632
- ZINC
- ZINC000034951255
- PDBe Ligand
- 228
- PDB Entries
- 2oro
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 0.321 mg/mL ALOGPS logP 2.24 ALOGPS logP 2.47 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 14.8 Chemaxon pKa (Strongest Basic) 5.64 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 94.4 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 125.17 m3·mol-1 Chemaxon Polarizability 44.69 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.8424 Caco-2 permeable - 0.5611 P-glycoprotein substrate Substrate 0.6188 P-glycoprotein inhibitor I Inhibitor 0.7187 P-glycoprotein inhibitor II Non-inhibitor 0.5782 Renal organic cation transporter Non-inhibitor 0.729 CYP450 2C9 substrate Non-substrate 0.8458 CYP450 2D6 substrate Non-substrate 0.7655 CYP450 3A4 substrate Substrate 0.5895 CYP450 1A2 substrate Inhibitor 0.8569 CYP450 2C9 inhibitor Non-inhibitor 0.8032 CYP450 2D6 inhibitor Inhibitor 0.765 CYP450 2C19 inhibitor Inhibitor 0.5317 CYP450 3A4 inhibitor Inhibitor 0.8826 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9093 Ames test Non AMES toxic 0.5657 Carcinogenicity Non-carcinogens 0.844 Biodegradation Not ready biodegradable 0.8524 Rat acute toxicity 2.4056 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8608 hERG inhibition (predictor II) Inhibitor 0.5247
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0000900000-8a5a34e3c43246e8574e Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0gb9-2092500000-280f97cee75f7304f7a8 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00dm-0615900000-28aadd9b9b32315653c3 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-106r-1494400000-12c821d166e3839ae603 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ab9-0963300000-8f2dac604d0f2b644128 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9444100000-c708c14dbd4bd467aaae Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 193.25322 predictedDeepCCS 1.0 (2019) [M+H]+ 195.64879 predictedDeepCCS 1.0 (2019) [M+Na]+ 201.57777 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsNitric oxide synthase, inducible
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body (PubMed:7504305, PubMed:7531687, PubMed:7544004, PubMed:7682706). In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such PTGS2/COX2 (By similarity). As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH on 'Cys-247' implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM (PubMed:25417112). Involved in inflammation, enhances the synthesis of pro-inflammatory mediators such as IL6 and IL8 (PubMed:19688109)
- Specific Function
- arginine binding
- Gene Name
- NOS2
- Uniprot ID
- P35228
- Uniprot Name
- Nitric oxide synthase, inducible
- Molecular Weight
- 131116.3 Da
References
- 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