7-(1,1-Dioxo-1h-Benzo[D]Isothiazol-3-Yloxymethyl)-2-(Oxalyl-Amino)-4,7-Dihydro-5h-Thieno[2,3-C]Pyran-3-Carboxylic Acid

Identification

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Name
7-(1,1-Dioxo-1h-Benzo[D]Isothiazol-3-Yloxymethyl)-2-(Oxalyl-Amino)-4,7-Dihydro-5h-Thieno[2,3-C]Pyran-3-Carboxylic Acid
Accession Number
DB02827  (EXPT01119)
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: 466.442
Monoisotopic: 466.014071436
Chemical Formula
C18H14N2O9S2
InChI Key
MDYIGSPVMWSFEZ-JTQLQIEISA-N
InChI
InChI=1S/C18H14N2O9S2/c21-14(18(24)25)19-16-12(17(22)23)9-5-6-28-10(13(9)30-16)7-29-15-8-3-1-2-4-11(8)31(26,27)20-15/h1-4,10H,5-7H2,(H,19,21)(H,22,23)(H,24,25)/t10-/m0/s1
IUPAC Name
(7S)-2-(carboxyformamido)-7-{[(1,1-dioxo-1λ⁶,2-benzothiazol-3-yl)oxy]methyl}-4H,5H,7H-thieno[2,3-c]pyran-3-carboxylic acid
SMILES
[H][C@@]1(COC2=NS(=O)(=O)C3=C2C=CC=C3)OCCC2=C1SC(NC(=O)C(O)=O)=C2C(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
446871
PubChem Substance
46504664
ChemSpider
394114
BindingDB
50299461
ChEMBL
CHEMBL577144
HET
DBD
PDB Entries
1l8g

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 Solubility0.0226 mg/mLALOGPS
logP0.81ALOGPS
logP2.29ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)-0.33ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area168.66 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity106.07 m3·mol-1ChemAxon
Polarizability43.09 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9142
Blood Brain Barrier-0.8364
Caco-2 permeable-0.6323
P-glycoprotein substrateSubstrate0.5126
P-glycoprotein inhibitor INon-inhibitor0.6018
P-glycoprotein inhibitor IINon-inhibitor0.6234
Renal organic cation transporterNon-inhibitor0.8308
CYP450 2C9 substrateNon-substrate0.6267
CYP450 2D6 substrateNon-substrate0.8061
CYP450 3A4 substrateNon-substrate0.5164
CYP450 1A2 substrateNon-inhibitor0.6701
CYP450 2C9 inhibitorNon-inhibitor0.6458
CYP450 2D6 inhibitorNon-inhibitor0.8835
CYP450 2C19 inhibitorNon-inhibitor0.6557
CYP450 3A4 inhibitorNon-inhibitor0.8761
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6476
Ames testNon AMES toxic0.5872
CarcinogenicityNon-carcinogens0.7751
BiodegradationNot ready biodegradable0.9873
Rat acute toxicity2.5290 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9654
hERG inhibition (predictor II)Inhibitor0.5187
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 alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Thienopyrans / Benzothiazoles / Thiophene carboxylic acids / N-arylamides / Pyrans / Benzenoids / Dicarboxylic acids and derivatives / Vinylogous amides / Organosulfonic acids and derivatives / Heteroaromatic compounds
show 9 more
Substituents
Alpha-amino acid or derivatives / 1,2-benzothiazole / Thienopyran / Thiophene carboxylic acid / Thiophene carboxylic acid or derivatives / N-arylamide / Dicarboxylic acid or derivatives / Pyran / Benzenoid / Vinylogous amide
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzothiazoles, dicarboxylic acid, thienopyran (CHEBI:41857)

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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  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. [PubMed:17016423]
  3. 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 June 13, 2005 07:24 / Updated on June 04, 2019 05:39