NAV

5-[(3R)-3-(5-methoxybiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine

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
3D
Similar Structures
Weight
Average: 358.4363
Monoisotopic: 358.179361346
Chemical Formula
C22H22N4O
Synonyms
Not Available
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot AvailableHumans
UDihydrofolate reductase (dfrB)Not AvailableStaphylococcus 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 outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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
PubChem Compound
25093369
PubChem Substance
99443611
ChemSpider
24691032
BindingDB
25826
ChEMBL
CHEMBL459177
ZINC
ZINC000040392373
PDBe Ligand
53R
PDB Entries
3eej / 3f0b / 3f0u

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 Solubility0.00385 mg/mLALOGPS
logP3.98ALOGPS
logP4.14Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)17.61Chemaxon
pKa (Strongest Basic)7.29Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area87.05 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity108.49 m3·mol-1Chemaxon
Polarizability40.69 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9924
Blood Brain Barrier+0.8939
Caco-2 permeable+0.7274
P-glycoprotein substrateNon-substrate0.6681
P-glycoprotein inhibitor INon-inhibitor0.8522
P-glycoprotein inhibitor IINon-inhibitor0.7762
Renal organic cation transporterNon-inhibitor0.8683
CYP450 2C9 substrateNon-substrate0.8363
CYP450 2D6 substrateNon-substrate0.843
CYP450 3A4 substrateNon-substrate0.5353
CYP450 1A2 substrateInhibitor0.7223
CYP450 2C9 inhibitorNon-inhibitor0.5784
CYP450 2D6 inhibitorNon-inhibitor0.9141
CYP450 2C19 inhibitorNon-inhibitor0.657
CYP450 3A4 inhibitorInhibitor0.5207
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6191
Ames testAMES toxic0.5087
CarcinogenicityNon-carcinogens0.9109
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2837 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9316
hERG inhibition (predictor II)Non-inhibitor0.6779
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/MSsplash10-0a4i-0009000000-8bfdf9a24aae4adb07d6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-ceff776ae975fdff50a0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05xu-0908000000-89b4461b6a383a0a9df8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fu-1198000000-ea36c01b83f68390d22a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001r-0945000000-ee15867b3d984e6b89c5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-3694000000-f84b2710866b087ddff4
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]-185.5081
predicted
DeepCCS 1.0 (2019)
[M+H]+187.86609
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.48622
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Dihydrofolate 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
  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]
Details2. Dihydrofolate 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
  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 21:19 / Updated at June 12, 2020 16:52