{4-[(2s,4e)-2-(1,3-Benzothiazol-2-Yl)-2-(1h-1,2,3-Benzotriazol-1-Yl)-5-Phenylpent-4-Enyl]Phenyl}(Difluoro)Methylphosphonic Acid

Identification

Generic Name
{4-[(2s,4e)-2-(1,3-Benzothiazol-2-Yl)-2-(1h-1,2,3-Benzotriazol-1-Yl)-5-Phenylpent-4-Enyl]Phenyl}(Difluoro)Methylphosphonic Acid
DrugBank Accession Number
DB04285
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 602.591
Monoisotopic: 602.135304298
Chemical Formula
C31H25F2N4O3PS
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UTyrosine-protein phosphatase non-receptor type 1Not AvailableHumans
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
Adverseeffects
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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 amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Benzotriazoles / Benzothiazoles / Styrenes / Triazoles / Thiazoles / Organic phosphonic acids / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organophosphorus compounds
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Substituents
1,2,3-triazole / 1,3-benzothiazole / Alkyl fluoride / Alkyl halide / Amphetamine or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzotriazole / Heteroaromatic compound
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, benzothiazoles, benzotriazoles (CHEBI:44768)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
GBLDYRVJENYQNH-AGLOJYHOSA-N
InChI
InChI=1S/C31H25F2N4O3PS/c32-31(33,41(38,39)40)24-18-16-23(17-19-24)21-30(20-8-11-22-9-2-1-3-10-22,29-34-26-13-5-7-15-28(26)42-29)37-27-14-6-4-12-25(27)35-36-37/h1-19H,20-21H2,(H2,38,39,40)/b11-8+/t30-/m1/s1
IUPAC Name
({4-[(2R,4E)-2-(1,3-benzothiazol-2-yl)-2-(1H-1,2,3-benzotriazol-1-yl)-5-phenylpent-4-en-1-yl]phenyl}difluoromethyl)phosphonic acid
SMILES
[H]\C(C[C@](CC1=CC=C(C=C1)C(F)(F)P(O)(O)=O)(N1N=NC2=CC=CC=C12)C1=NC2=CC=CC=C2S1)=C(\[H])C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
448025
PubChem Substance
46508576
ChemSpider
394957
ZINC
ZINC000014881165
PDBe Ligand
P90
PDB Entries
1q6n

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 Solubility0.0041 mg/mLALOGPS
logP5.46ALOGPS
logP5.84ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)0.72ChemAxon
pKa (Strongest Basic)2.02ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area101.13 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity169.77 m3·mol-1ChemAxon
Polarizability58.79 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8998
Blood Brain Barrier+0.9007
Caco-2 permeable-0.5676
P-glycoprotein substrateNon-substrate0.5551
P-glycoprotein inhibitor INon-inhibitor0.6058
P-glycoprotein inhibitor IINon-inhibitor0.8768
Renal organic cation transporterNon-inhibitor0.7863
CYP450 2C9 substrateNon-substrate0.6539
CYP450 2D6 substrateNon-substrate0.8178
CYP450 3A4 substrateNon-substrate0.6075
CYP450 1A2 substrateNon-inhibitor0.5682
CYP450 2C9 inhibitorNon-inhibitor0.6045
CYP450 2D6 inhibitorNon-inhibitor0.8752
CYP450 2C19 inhibitorNon-inhibitor0.5502
CYP450 3A4 inhibitorInhibitor0.74
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5696
Ames testNon AMES toxic0.5223
CarcinogenicityNon-carcinogens0.7667
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7264 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9386
hERG inhibition (predictor II)Non-inhibitor0.721
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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Tyrosine-protein phosphatase which acts as a regulator of endoplasmic reticulum unfolded protein response. Mediates dephosphorylation of EIF2AK3/PERK; inactivating the protein kinase activity of EI...
Gene Name
PTPN1
Uniprot ID
P18031
Uniprot Name
Tyrosine-protein phosphatase non-receptor type 1
Molecular Weight
49966.44 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