4-BROMO-3-(CARBOXYMETHOXY)-5-(4-HYDROXYPHENYL)THIOPHENE-2-CARBOXYLIC ACID

Identification

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Name
4-BROMO-3-(CARBOXYMETHOXY)-5-(4-HYDROXYPHENYL)THIOPHENE-2-CARBOXYLIC ACID
Accession Number
DB07197
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: 373.176
Monoisotopic: 371.930321357
Chemical Formula
C13H9BrO6S
InChI Key
QZWUMLLRAVGBHC-UHFFFAOYSA-N
InChI
InChI=1S/C13H9BrO6S/c14-9-10(20-5-8(16)17)12(13(18)19)21-11(9)6-1-3-7(15)4-2-6/h1-4,15H,5H2,(H,16,17)(H,18,19)
IUPAC Name
4-bromo-3-(carboxymethoxy)-5-(4-hydroxyphenyl)thiophene-2-carboxylic acid
SMILES
OC(=O)COC1=C(SC(=C1Br)C1=CC=C(O)C=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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
9547958
PubChem Substance
99443668
ChemSpider
7826889
BindingDB
14250
ChEMBL
CHEMBL214502
HET
694
PDB Entries
2h4g

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 Solubility0.0124 mg/mLALOGPS
logP2.85ALOGPS
logP2.97ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity77.28 m3·mol-1ChemAxon
Polarizability31.15 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9446
Blood Brain Barrier+0.7675
Caco-2 permeable-0.6286
P-glycoprotein substrateNon-substrate0.6037
P-glycoprotein inhibitor INon-inhibitor0.8546
P-glycoprotein inhibitor IINon-inhibitor0.7142
Renal organic cation transporterNon-inhibitor0.8923
CYP450 2C9 substrateNon-substrate0.7939
CYP450 2D6 substrateNon-substrate0.887
CYP450 3A4 substrateNon-substrate0.7072
CYP450 1A2 substrateNon-inhibitor0.5845
CYP450 2C9 inhibitorNon-inhibitor0.6496
CYP450 2D6 inhibitorNon-inhibitor0.886
CYP450 2C19 inhibitorNon-inhibitor0.7738
CYP450 3A4 inhibitorNon-inhibitor0.9176
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5714
Ames testNon AMES toxic0.8276
CarcinogenicityNon-carcinogens0.8706
BiodegradationNot ready biodegradable0.8487
Rat acute toxicity2.5740 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.995
hERG inhibition (predictor II)Non-inhibitor0.8968
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 thiophene carboxylic acids. These are compounds containing a thiophene ring which bears a carboxylic acid group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thiophenes
Sub Class
Thiophene carboxylic acids and derivatives
Direct Parent
Thiophene carboxylic acids
Alternative Parents
Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Dicarboxylic acids and derivatives / Benzene and substituted derivatives / Aryl bromides / Heteroaromatic compounds / Carboxylic acids / Organobromides / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Thiophene carboxylic acid / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Phenol / Aryl bromide / Aryl halide / Benzenoid / Monocyclic benzene moiety / Dicarboxylic acid or derivatives / Heteroaromatic compound
show 11 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 15:19 / Updated on June 04, 2019 06:36