NAV

3-(5-amino-7-hydroxy-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-N-(3,5-dichlorobenzyl)-benzamide

Identification

Generic Name
3-(5-amino-7-hydroxy-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-N-(3,5-dichlorobenzyl)-benzamide
DrugBank Accession Number
DB03571
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 430.248
Monoisotopic: 429.050778109
Chemical Formula
C18H13Cl2N7O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDihydroneopterin aldolaseNot AvailableStaphylococcus aureus
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 n-benzylbenzamides. These are compounds containing a benzamide moiety that is N-linked to a benzyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
N-benzylbenzamides
Alternative Parents
Phenyl-1,2,3-triazoles / Triazolopyrimidines / Benzoyl derivatives / Dichlorobenzenes / Pyrimidones / Aminopyrimidines and derivatives / Aryl chlorides / Vinylogous amides / Heteroaromatic compounds / Secondary carboxylic acid amides
show 8 more
Substituents
1,2,3-triazole / 1,3-dichlorobenzene / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzamides, dichlorobenzene, triazolopyrimidines (CHEBI:47115)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
JMQTXEWNXSPEKX-UHFFFAOYSA-N
InChI
InChI=1S/C18H13Cl2N7O2/c19-11-4-9(5-12(20)7-11)8-22-16(28)10-2-1-3-13(6-10)27-25-14-15(26-27)23-18(21)24-17(14)29/h1-7H,8H2,(H,22,28)(H3,21,23,24,26,29)
IUPAC Name
3-{5-amino-7-hydroxy-2H-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl}-N-[(3,5-dichlorophenyl)methyl]benzamide
SMILES
NC1=NC2=NN(N=C2C(O)=N1)C1=CC(=CC=C1)C(=O)NCC1=CC(Cl)=CC(Cl)=C1

References

General References
Not Available
PubChem Compound
448407
PubChem Substance
46505855
ChemSpider
395215
BindingDB
50143043
ChEMBL
CHEMBL44803
ZINC
ZINC000013559919
PDBe Ligand
45P
PDB Entries
1rs4

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 Solubility0.019 mg/mLALOGPS
logP3.04ALOGPS
logP3.36Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)10.57Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area131.84 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity122.75 m3·mol-1Chemaxon
Polarizability41.54 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9488
Caco-2 permeable-0.6348
P-glycoprotein substrateNon-substrate0.6529
P-glycoprotein inhibitor INon-inhibitor0.9147
P-glycoprotein inhibitor IINon-inhibitor0.5621
Renal organic cation transporterNon-inhibitor0.8391
CYP450 2C9 substrateNon-substrate0.7983
CYP450 2D6 substrateNon-substrate0.8077
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.5396
CYP450 2C9 inhibitorNon-inhibitor0.7385
CYP450 2D6 inhibitorNon-inhibitor0.8755
CYP450 2C19 inhibitorNon-inhibitor0.8487
CYP450 3A4 inhibitorNon-inhibitor0.7939
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.75
Ames testNon AMES toxic0.5451
CarcinogenicityNon-carcinogens0.7985
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4919 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8286
hERG inhibition (predictor II)Non-inhibitor0.6848
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/MSsplash10-0a59-0270900000-417cfcb121b7573b2b4f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00b9-0910700000-dde32b75b9dd685bcff1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-0050900000-b90ae2c952752523f88e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kaj-4932100000-cebe5f56f61419e6dfd1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052u-0952100000-ce6b40a83630b948dbda
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-9100000000-45ebec3b62e16be30f38
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]-188.35939
predicted
DeepCCS 1.0 (2019)
[M+H]+190.75493
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.66747
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dihydroneopterin aldolase
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Isomerase activity
Specific Function
Catalyzes the conversion of 7,8-dihydroneopterin to 6-hydroxymethyl-7,8-dihydropterin. Can also catalyze the epimerization of carbon 2' of dihydroneopterin to dihydromonapterin.
Gene Name
folB
Uniprot ID
P56740
Uniprot Name
Dihydroneopterin aldolase
Molecular Weight
13750.58 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]
  3. 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52