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3-(5-Amino-7-oxo-3,7-dihydro-2H-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-N-(2-{[2-(hydroxymethyl)phenyl]sulfanyl}benzyl)benzamide

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Identification

Generic Name
3-(5-Amino-7-oxo-3,7-dihydro-2H-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-N-(2-{[2-(hydroxymethyl)phenyl]sulfanyl}benzyl)benzamide
DrugBank Accession Number
DB03231
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 499.544
Monoisotopic: 499.142658263
Chemical Formula
C25H21N7O3S
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
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
Diarylthioethers / Phenyl-1,2,3-triazoles / Triazolopyrimidines / Thiophenol ethers / Benzoyl derivatives / Benzyl alcohols / Aminopyrimidines and derivatives / Pyrimidones / Vinylogous amides / Heteroaromatic compounds
show 10 more
Substituents
1,2,3-triazole / Alcohol / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic alcohol / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azole
show 29 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
IXDQOBDHBWEZOH-UHFFFAOYSA-N
InChI
InChI=1S/C25H21N7O3S/c26-25-28-22-21(24(35)29-25)30-32(31-22)18-9-5-8-15(12-18)23(34)27-13-16-6-1-3-10-19(16)36-20-11-4-2-7-17(20)14-33/h1-12,33H,13-14H2,(H,27,34)(H3,26,28,29,31,35)
IUPAC Name
3-{5-amino-7-oxo-2H,3H,7H-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl}-N-[(2-{[2-(hydroxymethyl)phenyl]sulfanyl}phenyl)methyl]benzamide
SMILES
[H]N([H])C1=NC(=O)C2=NN(N([H])C2=N1)C1=CC=CC(=C1)C(=O)N([H])CC1=CC=CC=C1SC1=CC=CC=C1CO

References

General References
Not Available
PubChem Compound
448408
PubChem Substance
46506254
ChemSpider
395216
BindingDB
50143049
ChEMBL
CHEMBL297273
ZINC
ZINC000013559921
PDBe Ligand
PSB
PDB Entries
1rsd

Clinical Trials

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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 Solubility0.0321 mg/mLALOGPS
logP2.63ALOGPS
logP1.75Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.62Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area144.77 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity149.46 m3·mol-1Chemaxon
Polarizability51.92 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8765
Caco-2 permeable-0.6168
P-glycoprotein substrateNon-substrate0.6345
P-glycoprotein inhibitor INon-inhibitor0.8868
P-glycoprotein inhibitor IINon-inhibitor0.7565
Renal organic cation transporterNon-inhibitor0.8498
CYP450 2C9 substrateNon-substrate0.7327
CYP450 2D6 substrateNon-substrate0.8259
CYP450 3A4 substrateNon-substrate0.6277
CYP450 1A2 substrateNon-inhibitor0.6261
CYP450 2C9 inhibitorNon-inhibitor0.7201
CYP450 2D6 inhibitorNon-inhibitor0.8497
CYP450 2C19 inhibitorNon-inhibitor0.6656
CYP450 3A4 inhibitorNon-inhibitor0.5097
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5748
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.7887
BiodegradationNot ready biodegradable0.996
Rat acute toxicity2.4762 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9652
hERG inhibition (predictor II)Non-inhibitor0.6191
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/MSsplash10-0udi-0011190000-0f9ddba312c7ec5ccc38
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-052e-0333900000-a9c3a09f7e1e4f048fdd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-0019010000-05c05e89cef5e1064969
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pba-0913500000-8bbedfc8d31493254951
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-1591110000-17104171ad91f813fd50
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-7438900000-97cbe69494362621c0a3
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]-199.26479
predicted
DeepCCS 1.0 (2019)
[M+H]+201.66035
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.57289
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]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52