5-[(3R)-3-(5-methoxybiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
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Identification
- Generic Name
- 5-[(3R)-3-(5-methoxybiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
- DrugBank Accession Number
- DB07140
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 358.4363
Monoisotopic: 358.179361346 - Chemical Formula
- C22H22N4O
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDihydrofolate reductase Not Available Humans UDihydrofolate reductase (dfrB) Not Available Staphylococcus aureus (strain bovine RF122 / ET3-1) - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Biphenyls and derivatives
- Direct Parent
- Biphenyls and derivatives
- Alternative Parents
- Phenoxy compounds / Methoxybenzenes / Anisoles / Aminopyrimidines and derivatives / Alkyl aryl ethers / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds show 1 more
- Substituents
- Alkyl aryl ether / Amine / Aminopyrimidine / Anisole / Aromatic heteromonocyclic compound / Azacycle / Biphenyl / Ether / Heteroaromatic compound / Hydrocarbon derivative show 12 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- JPENSYBRTSIYGO-AWEZNQCLSA-N
- InChI
- InChI=1S/C22H22N4O/c1-14(9-10-20-15(2)25-22(24)26-21(20)23)17-11-18(13-19(12-17)27-3)16-7-5-4-6-8-16/h4-8,11-14H,1-3H3,(H4,23,24,25,26)/t14-/m0/s1
- IUPAC Name
- 5-[(3R)-3-{5-methoxy-[1,1'-biphenyl]-3-yl}but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
- SMILES
- [H][C@](C)(C#CC1=C(C)N=C(N)N=C1N)C1=CC(OC)=CC(=C1)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 25093369
- PubChem Substance
- 99443611
- ChemSpider
- 24691032
- BindingDB
- 25826
- ChEMBL
- CHEMBL459177
- ZINC
- ZINC000040392373
- PDBe Ligand
- 53R
- PDB Entries
- 3eej / 3f0b / 3f0u
Clinical Trials
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 0.00385 mg/mL ALOGPS logP 3.98 ALOGPS logP 4.14 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) 17.61 Chemaxon pKa (Strongest Basic) 7.29 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 87.05 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 108.49 m3·mol-1 Chemaxon Polarizability 40.69 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9924 Blood Brain Barrier + 0.8939 Caco-2 permeable + 0.7274 P-glycoprotein substrate Non-substrate 0.6681 P-glycoprotein inhibitor I Non-inhibitor 0.8522 P-glycoprotein inhibitor II Non-inhibitor 0.7762 Renal organic cation transporter Non-inhibitor 0.8683 CYP450 2C9 substrate Non-substrate 0.8363 CYP450 2D6 substrate Non-substrate 0.843 CYP450 3A4 substrate Non-substrate 0.5353 CYP450 1A2 substrate Inhibitor 0.7223 CYP450 2C9 inhibitor Non-inhibitor 0.5784 CYP450 2D6 inhibitor Non-inhibitor 0.9141 CYP450 2C19 inhibitor Non-inhibitor 0.657 CYP450 3A4 inhibitor Inhibitor 0.5207 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6191 Ames test AMES toxic 0.5087 Carcinogenicity Non-carcinogens 0.9109 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.2837 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9316 hERG inhibition (predictor II) Non-inhibitor 0.6779
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-8bfdf9a24aae4adb07d6 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-ceff776ae975fdff50a0 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-05xu-0908000000-89b4461b6a383a0a9df8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-05fu-1198000000-ea36c01b83f68390d22a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001r-0945000000-ee15867b3d984e6b89c5 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-052f-3694000000-f84b2710866b087ddff4 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]- 185.5081 predictedDeepCCS 1.0 (2019) [M+H]+ 187.86609 predictedDeepCCS 1.0 (2019) [M+Na]+ 194.48622 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsDihydrofolate reductase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nadph binding
- Specific Function
- Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA pre...
- Gene Name
- DHFR
- Uniprot ID
- P00374
- Uniprot Name
- Dihydrofolate reductase
- Molecular Weight
- 21452.61 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]
2. DetailsDihydrofolate reductase (dfrB)
- Kind
- Protein
- Organism
- Staphylococcus aureus (strain bovine RF122 / ET3-1)
- Pharmacological action
- Unknown
- General Function
- Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis.
- Specific Function
- Dihydrofolate reductase activity
- Gene Name
- dfrB
- Uniprot ID
- A0A0M3KKX1
- Uniprot Name
- Dihydrofolate reductase
- Molecular Weight
- 17991.48 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 21:19 / Updated at June 12, 2020 16:52