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

Identification

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Name
4-BROMO-3-(CARBOXYMETHOXY)-5-[3-(CYCLOHEXYLAMINO)PHENYL]THIOPHENE-2-CARBOXYLIC ACID
Accession Number
DB06829
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: 454.335
Monoisotopic: 453.024556092
Chemical Formula
C19H20BrNO5S
InChI Key
RXDVFLTWXCTCEX-UHFFFAOYSA-N
InChI
InChI=1S/C19H20BrNO5S/c20-15-16(26-10-14(22)23)18(19(24)25)27-17(15)11-5-4-8-13(9-11)21-12-6-2-1-3-7-12/h4-5,8-9,12,21H,1-3,6-7,10H2,(H,22,23)(H,24,25)
IUPAC Name
4-bromo-3-(carboxymethoxy)-5-[3-(cyclohexylamino)phenyl]thiophene-2-carboxylic acid
SMILES
OC(=O)COC1=C(SC(=C1Br)C1=CC=CC(NC2CCCCC2)=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
17759780
PubChem Substance
99443300
ChemSpider
22376100
BindingDB
50219597
ChEMBL
CHEMBL243940
HET
024
PDB Entries
2qbs

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 Solubility0.000901 mg/mLALOGPS
logP4.52ALOGPS
logP2.93ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)4.88ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.86 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity106.5 m3·mol-1ChemAxon
Polarizability42.62 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8656
Blood Brain Barrier+0.7121
Caco-2 permeable-0.6528
P-glycoprotein substrateSubstrate0.5246
P-glycoprotein inhibitor INon-inhibitor0.6472
P-glycoprotein inhibitor IIInhibitor0.6708
Renal organic cation transporterNon-inhibitor0.7393
CYP450 2C9 substrateNon-substrate0.7275
CYP450 2D6 substrateNon-substrate0.8159
CYP450 3A4 substrateNon-substrate0.5323
CYP450 1A2 substrateInhibitor0.5717
CYP450 2C9 inhibitorNon-inhibitor0.5059
CYP450 2D6 inhibitorNon-inhibitor0.8411
CYP450 2C19 inhibitorInhibitor0.5458
CYP450 3A4 inhibitorNon-inhibitor0.7694
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6633
Ames testNon AMES toxic0.7065
CarcinogenicityNon-carcinogens0.9144
BiodegradationNot ready biodegradable0.9756
Rat acute toxicity2.6001 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9786
hERG inhibition (predictor II)Non-inhibitor0.6045
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 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
Phenylalkylamines / Aniline and substituted anilines / Secondary alkylarylamines / Cyclohexylamines / Alkyl aryl ethers / Dicarboxylic acids and derivatives / Aryl bromides / Heteroaromatic compounds / Amino acids / Carboxylic acids
show 5 more
Substituents
Phenylalkylamine / Aniline or substituted anilines / Thiophene carboxylic acid / Alkyl aryl ether / Cyclohexylamine / Secondary aliphatic/aromatic amine / Dicarboxylic acid or derivatives / Aryl bromide / Aryl halide / Monocyclic benzene moiety
show 20 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 15:16 / Updated on June 04, 2019 06:30