NAV

2,4-Diamino-6-[N-(2',5'-Dimethoxybenzyl)-N-Methylamino]Quinazoline

Identification

Generic Name
2,4-Diamino-6-[N-(2',5'-Dimethoxybenzyl)-N-Methylamino]Quinazoline
DrugBank Accession Number
DB02427
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 339.3916
Monoisotopic: 339.169524941
Chemical Formula
C18H21N5O2
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 reductaseNot AvailableHumans
UDihydrofolate reductaseNot AvailablePneumocystis carinii
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 quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazanaphthalenes
Sub Class
Benzodiazines
Direct Parent
Quinazolinamines
Alternative Parents
Dimethoxybenzenes / Phenylmethylamines / Phenoxy compounds / Dialkylarylamines / Benzylamines / Anisoles / Aralkylamines / Aminopyrimidines and derivatives / Alkyl aryl ethers / Imidolactams
show 5 more
Substituents
Alkyl aryl ether / Amine / Aminopyrimidine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzylamine / Dialkylarylamine
show 21 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
YBJANOUTWRTBDK-UHFFFAOYSA-N
InChI
InChI=1S/C18H21N5O2/c1-23(10-11-8-13(24-2)5-7-16(11)25-3)12-4-6-15-14(9-12)17(19)22-18(20)21-15/h4-9H,10H2,1-3H3,(H4,19,20,21,22)
IUPAC Name
N6-[(2,5-dimethoxyphenyl)methyl]-N6-methylquinazoline-2,4,6-triamine
SMILES
COC1=CC(CN(C)C2=CC=C3N=C(N)N=C(N)C3=C2)=C(OC)C=C1

References

General References
Not Available
PubChem Compound
447021
PubChem Substance
46507703
ChemSpider
394233
BindingDB
50066490
ChEMBL
CHEMBL325434
ZINC
ZINC000002047759
PDBe Ligand
COG
PDB Entries
1ly3

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 Solubility0.213 mg/mLALOGPS
logP2.68ALOGPS
logP2.56Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)18.54Chemaxon
pKa (Strongest Basic)7.4Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area99.52 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity100.43 m3·mol-1Chemaxon
Polarizability35.66 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier+0.9595
Caco-2 permeable+0.6184
P-glycoprotein substrateSubstrate0.5647
P-glycoprotein inhibitor IInhibitor0.5502
P-glycoprotein inhibitor IIInhibitor0.8291
Renal organic cation transporterNon-inhibitor0.6927
CYP450 2C9 substrateNon-substrate0.8758
CYP450 2D6 substrateNon-substrate0.8004
CYP450 3A4 substrateSubstrate0.5978
CYP450 1A2 substrateInhibitor0.5877
CYP450 2C9 inhibitorNon-inhibitor0.5609
CYP450 2D6 inhibitorInhibitor0.7476
CYP450 2C19 inhibitorNon-inhibitor0.6783
CYP450 3A4 inhibitorNon-inhibitor0.5515
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5928
Ames testAMES toxic0.5935
CarcinogenicityNon-carcinogens0.9054
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6084 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6412
hERG inhibition (predictor II)Inhibitor0.746
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/MSsplash10-0006-0109000000-dad2a31269cbd599bdf5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0916000000-a5a4af858ec1fd81f880
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6x-0669000000-243fd00f8c4a3bafff17
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000j-2769000000-c8a845d6e5df2875fd17
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-0940000000-bb5ef03aed9bf3d26c5b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-5970000000-a12851dac501c171eb0f
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]-190.17696
predicted
DeepCCS 1.0 (2019)
[M+H]+192.65822
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.50356
predicted
DeepCCS 1.0 (2019)

Targets

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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
Kind
Protein
Organism
Pneumocystis carinii
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis.
Gene Name
Not Available
Uniprot ID
P16184
Uniprot Name
Dihydrofolate reductase
Molecular Weight
23883.325 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:16