NAV

6-methyl-5-[3-methyl-3-(3,4,5-trimethoxyphenyl)but-1-yn-1-yl]pyrimidine-2,4-diamine

Identification

Generic Name
6-methyl-5-[3-methyl-3-(3,4,5-trimethoxyphenyl)but-1-yn-1-yl]pyrimidine-2,4-diamine
DrugBank Accession Number
DB07153
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 356.4189
Monoisotopic: 356.184840654
Chemical Formula
C19H24N4O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
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
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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 phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
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 / Ether / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam
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
FJNFXXGWYVMQNA-UHFFFAOYSA-N
InChI
InChI=1S/C19H24N4O3/c1-11-13(17(20)23-18(21)22-11)7-8-19(2,3)12-9-14(24-4)16(26-6)15(10-12)25-5/h9-10H,1-6H3,(H4,20,21,22,23)
IUPAC Name
6-methyl-5-[3-methyl-3-(3,4,5-trimethoxyphenyl)but-1-yn-1-yl]pyrimidine-2,4-diamine
SMILES
COC1=CC(=CC(OC)=C1OC)C(C)(C)C#CC1=C(C)N=C(N)N=C1N

References

General References
Not Available
PubChem Compound
25187896
PubChem Substance
99443624
ChemSpider
25056715
BindingDB
50329608
ChEMBL
CHEMBL1230365
ZINC
ZINC000053683841
PDBe Ligand
55V
PDB Entries
3fqc / 3fqf / 3qls / 3qly

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 Solubility0.0115 mg/mLALOGPS
logP2.94ALOGPS
logP2.48Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)17.61Chemaxon
pKa (Strongest Basic)7.29Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area105.51 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity100.76 m3·mol-1Chemaxon
Polarizability39.02 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9862
Blood Brain Barrier+0.777
Caco-2 permeable+0.7131
P-glycoprotein substrateNon-substrate0.5154
P-glycoprotein inhibitor INon-inhibitor0.796
P-glycoprotein inhibitor IINon-inhibitor0.912
Renal organic cation transporterNon-inhibitor0.9
CYP450 2C9 substrateNon-substrate0.8672
CYP450 2D6 substrateNon-substrate0.8671
CYP450 3A4 substrateSubstrate0.5059
CYP450 1A2 substrateNon-inhibitor0.6698
CYP450 2C9 inhibitorNon-inhibitor0.6515
CYP450 2D6 inhibitorNon-inhibitor0.9552
CYP450 2C19 inhibitorNon-inhibitor0.6427
CYP450 3A4 inhibitorNon-inhibitor0.607
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5578
Ames testNon AMES toxic0.7328
CarcinogenicityNon-carcinogens0.9138
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2355 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.988
hERG inhibition (predictor II)Non-inhibitor0.8813
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-052f-0429000000-4f5aa1580632db971e0c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-052o-0913000000-55503da2921e81936a84
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-b080ef7b59f9098531f3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0019000000-a3afdd3bba423bb557ab
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01du-0796000000-ab37a7b5a12975ba9b18
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dm-4912000000-d788c613e811bc7deee7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ya-0931000000-ed76b03a3c817108d1d7
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]-181.04189
predicted
DeepCCS 1.0 (2019)
[M+H]+183.39989
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.46245
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 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