5-[3-(BENZYLAMINO)PHENYL]-4-BROMO-3-(CARBOXYMETHOXY)THIOPHENE-2-CARBOXYLIC ACID

Identification

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Name
5-[3-(BENZYLAMINO)PHENYL]-4-BROMO-3-(CARBOXYMETHOXY)THIOPHENE-2-CARBOXYLIC ACID
Accession Number
DB07289
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: 462.314
Monoisotopic: 460.993255964
Chemical Formula
C20H16BrNO5S
InChI Key
XEQPGVUGYAUMSA-UHFFFAOYSA-N
InChI
InChI=1S/C20H16BrNO5S/c21-16-17(27-11-15(23)24)19(20(25)26)28-18(16)13-7-4-8-14(9-13)22-10-12-5-2-1-3-6-12/h1-9,22H,10-11H2,(H,23,24)(H,25,26)
IUPAC Name
5-[3-(benzylamino)phenyl]-4-bromo-3-(carboxymethoxy)thiophene-2-carboxylic acid
SMILES
OC(=O)COC1=C(SC(=C1Br)C1=CC=CC(NCC2=CC=CC=C2)=C1)C(O)=O

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
PubChem Compound
17758920
PubChem Substance
99443760
ChemSpider
22376415
BindingDB
50219574
ChEMBL
CHEMBL243731
HET
910
PDB Entries
2qbr

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 Solubility0.000868 mg/mLALOGPS
logP4.3ALOGPS
logP3.62ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)3.58ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.86 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity110.1 m3·mol-1ChemAxon
Polarizability42.94 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8853
Blood Brain Barrier+0.6901
Caco-2 permeable-0.6212
P-glycoprotein substrateNon-substrate0.5497
P-glycoprotein inhibitor INon-inhibitor0.5816
P-glycoprotein inhibitor IIInhibitor0.833
Renal organic cation transporterNon-inhibitor0.8287
CYP450 2C9 substrateNon-substrate0.7504
CYP450 2D6 substrateNon-substrate0.8346
CYP450 3A4 substrateNon-substrate0.6816
CYP450 1A2 substrateNon-inhibitor0.5076
CYP450 2C9 inhibitorInhibitor0.5874
CYP450 2D6 inhibitorNon-inhibitor0.7754
CYP450 2C19 inhibitorInhibitor0.5819
CYP450 3A4 inhibitorNon-inhibitor0.7391
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8177
Ames testNon AMES toxic0.7202
CarcinogenicityNon-carcinogens0.7891
BiodegradationNot ready biodegradable0.9869
Rat acute toxicity2.4474 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.99
hERG inhibition (predictor II)Non-inhibitor0.6264
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 phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylmethylamines
Direct Parent
Phenylbenzamines
Alternative Parents
Thiophene carboxylic acids / Phenylalkylamines / Aniline and substituted anilines / Benzylamines / Secondary alkylarylamines / Alkyl aryl ethers / Aryl bromides / Dicarboxylic acids and derivatives / Heteroaromatic compounds / Amino acids
show 6 more
Substituents
Phenylbenzamine / Benzylamine / Thiophene carboxylic acid / Thiophene carboxylic acid or derivatives / Aniline or substituted anilines / Phenylalkylamine / Alkyl aryl ether / Secondary aliphatic/aromatic amine / Aralkylamine / Aryl bromide
show 23 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

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. 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 15:20 / Updated on September 02, 2019 18:34