(2R,6S)-6-{[methyl(3,4,5-trimethoxyphenyl)amino]methyl}-1,2,5,6,7,8-hexahydroquinazoline-2,4-diamine

Identification

Name
(2R,6S)-6-{[methyl(3,4,5-trimethoxyphenyl)amino]methyl}-1,2,5,6,7,8-hexahydroquinazoline-2,4-diamine
Accession Number
DB08642
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 375.4653
Monoisotopic: 375.227039819
Chemical Formula
C19H29N5O3
InChI Key
JJWPLCQODKLEHY-JEOXALJRSA-N
InChI
InChI=1S/C19H29N5O3/c1-24(12-8-15(25-2)17(27-4)16(9-12)26-3)10-11-5-6-14-13(7-11)18(20)23-19(21)22-14/h8-9,11,19,22H,5-7,10,21H2,1-4H3,(H2,20,23)/t11-,19+/m0/s1
IUPAC Name
(2R,6S)-6-{[methyl(3,4,5-trimethoxyphenyl)amino]methyl}-1,2,5,6,7,8-hexahydroquinazoline-2,4-diamine
SMILES
[H][[email protected]]1(CN(C)C2=CC(OC)=C(OC)C(OC)=C2)CCC2=C(C1)C(N)=N[[email protected]]([H])(N)N2

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
46937168
PubChem Substance
99445113
ChemSpider
25060059
HET
TQD
PDB Entries
1s3u / 1s3v

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.237 mg/mLALOGPS
logP1.3ALOGPS
logP1ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)7.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area107.36 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity106.33 m3·mol-1ChemAxon
Polarizability41.65 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9933
Blood Brain Barrier+0.6508
Caco-2 permeable-0.5294
P-glycoprotein substrateSubstrate0.9276
P-glycoprotein inhibitor IInhibitor0.7318
P-glycoprotein inhibitor IIInhibitor0.5505
Renal organic cation transporterInhibitor0.5
CYP450 2C9 substrateNon-substrate0.8486
CYP450 2D6 substrateNon-substrate0.789
CYP450 3A4 substrateSubstrate0.6756
CYP450 1A2 substrateNon-inhibitor0.7148
CYP450 2C9 inhibitorNon-inhibitor0.7384
CYP450 2D6 inhibitorNon-inhibitor0.6748
CYP450 2C19 inhibitorNon-inhibitor0.7039
CYP450 3A4 inhibitorNon-inhibitor0.8892
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7777
Ames testNon AMES toxic0.5757
CarcinogenicityNon-carcinogens0.9128
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7154 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5517
hERG inhibition (predictor II)Non-inhibitor0.5294
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as quinazolines. These are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazanaphthalenes
Sub Class
Benzodiazines
Direct Parent
Quinazolines
Alternative Parents
Aminophenyl ethers / Methoxyanilines / Phenoxy compounds / Methoxybenzenes / Anisoles / Dialkylarylamines / Alkyl aryl ethers / Aminopyrimidines and derivatives / Imidolactams / Hydropyrimidines
show 10 more
Substituents
Quinazoline / Methoxyaniline / Aminophenyl ether / Phenol ether / Tertiary aliphatic/aromatic amine / Dialkylarylamine / Aniline or substituted anilines / Phenoxy compound / Methoxybenzene / Anisole
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:33 / Updated on December 01, 2017 16:07