NAV

6-amino-4-(2-phenylethyl)-1,7-dihydro-8H-imidazo[4,5-g]quinazolin-8-one

Identification

Generic Name
6-amino-4-(2-phenylethyl)-1,7-dihydro-8H-imidazo[4,5-g]quinazolin-8-one
DrugBank Accession Number
DB08267
Background

6-amino-4-(2-phenylethyl)-1,7-dihydro-8H-imidazo[4,5-g]quinazolin-8-one is a solid. This compound belongs to the stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. It is known to target queuine tRNA-ribosyltransferase.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 305.3339
Monoisotopic: 305.127660127
Chemical Formula
C17H15N5O
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UQueuine tRNA-ribosyltransferaseNot AvailableZymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4)
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 stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Quinazolinamines / Benzimidazoles / Pyrimidones / Aminopyrimidines and derivatives / Benzene and substituted derivatives / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Primary amines
show 4 more
Substituents
Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / Diazanaphthalene / Heteroaromatic compound / Hydrocarbon derivative
show 16 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
PBZAIUVFRISTSZ-UHFFFAOYSA-N
InChI
InChI=1S/C17H15N5O/c18-17-21-14-11(7-6-10-4-2-1-3-5-10)15-13(19-9-20-15)8-12(14)16(23)22-17/h1-5,8-9H,6-7H2,(H,19,20)(H3,18,21,22,23)
IUPAC Name
6-amino-4-(2-phenylethyl)-1H,7H,8H-imidazo[4,5-g]quinazolin-8-one
SMILES
NC1=NC2=C(C=C3NC=NC3=C2CCC2=CC=CC=C2)C(=O)N1

References

General References
Not Available
PubChem Compound
5326928
PubChem Substance
99444738
ChemSpider
4484211
ZINC
ZINC000033836604
PDBe Ligand
NE8
PDB Entries
1y5v / 5i07 / 6ygr / 6ygz

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 Solubility0.0325 mg/mLALOGPS
logP1.91ALOGPS
logP2.32Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)11.09Chemaxon
pKa (Strongest Basic)4.15Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area96.16 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity89.44 m3·mol-1Chemaxon
Polarizability32.31 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9638
Blood Brain Barrier+0.9797
Caco-2 permeable-0.6195
P-glycoprotein substrateNon-substrate0.6014
P-glycoprotein inhibitor INon-inhibitor0.8197
P-glycoprotein inhibitor IINon-inhibitor0.7344
Renal organic cation transporterNon-inhibitor0.627
CYP450 2C9 substrateNon-substrate0.8077
CYP450 2D6 substrateNon-substrate0.7585
CYP450 3A4 substrateNon-substrate0.6259
CYP450 1A2 substrateNon-inhibitor0.5221
CYP450 2C9 inhibitorNon-inhibitor0.8084
CYP450 2D6 inhibitorNon-inhibitor0.6787
CYP450 2C19 inhibitorNon-inhibitor0.72
CYP450 3A4 inhibitorNon-inhibitor0.6949
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5515
Ames testNon AMES toxic0.5424
CarcinogenicityNon-carcinogens0.9675
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.3915 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8799
hERG inhibition (predictor II)Non-inhibitor0.7858
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-d7fd1124ba24c89ed951
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f79-0095000000-24f081916916891f887a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0019000000-3bda6dc6b42faa111d78
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kto-2092000000-5805c5751c2d7f33d413
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06z0-0391000000-d40d6cf16ba82053e0f9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-4490000000-5df212cbf0e485e5a7d1
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]-166.0865
predicted
DeepCCS 1.0 (2019)
[M+H]+168.4445
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.53764
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Queuine tRNA-ribosyltransferase
Kind
Protein
Organism
Zymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4)
Pharmacological action
Unknown
General Function
Queuine trna-ribosyltransferase activity
Specific Function
Exchanges the guanine residue with 7-aminomethyl-7-deazaguanine in tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr). After this exchange, a cyclopentendiol moiety is attached to the 7-am...
Gene Name
tgt
Uniprot ID
P28720
Uniprot Name
Queuine tRNA-ribosyltransferase
Molecular Weight
42842.235 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 21:30 / Updated at June 12, 2020 16:52