TrxR1 prodrug 5u   Click here for help

GtoPdb Ligand ID: 13698

Compound class: Synthetic organic
Comment: This small molecule is a prodrug that produces an active compound that is a covalent inhibitor of thioredoxin reductase 1 (TrxR1) [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 151.56
Molecular weight 482.62
XLogP 2.4
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCNC(=O)O[C@@H]1/C=C(\C)/C[C@H]2/C=C(/C[C@H]3[C@H]1[C@@H](CSC(=S)N(C)C)C(=O)O3)\C(=O)O2
Isomeric SMILES C(CC)NC(O[C@H]\1[C@H]2[C@H](C/C=3/C(O[C@@H](C/C(=C1)/C)\C3)=O)OC([C@@H]2CSC(N(C)C)=S)=O)=O
InChI InChI=1S/C22H30N2O6S2/c1-5-6-23-21(27)30-16-8-12(2)7-14-9-13(19(25)28-14)10-17-18(16)15(20(26)29-17)11-32-22(31)24(3)4/h8-9,14-18H,5-7,10-11H2,1-4H3,(H,23,27)/b12-8+/t14-,15+,16+,17-,18-/m0/s1
InChI Key VICRWBYOKZPFHL-QSGXIYJFSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form TrxR1 inhibitor 6a
IUPAC Name Click here for help
(3R,3aR,4R,5E,8S,11Z,12aS)-3-(((Dimethylcarbamothioyl)thio)methyl)-6-methyl-2,10-dioxo-2,3,3a,4,7,8,12,12a-octahydro-10H-8,11-(metheno)furo[2,3-e][1]oxacycloundecin-4-yl propylcarbamate
Database Links Click here for help
GtoPdb PubChem SID 507750332
PubChem CID 172676879
Search Google for chemical match using the InChIKey VICRWBYOKZPFHL-QSGXIYJFSA-N
Search Google for chemicals with the same backbone VICRWBYOKZPFHL
UniChem Compound Search for chemical match using the InChIKey VICRWBYOKZPFHL-QSGXIYJFSA-N
UniChem Connectivity Search for chemical match using the InChIKey VICRWBYOKZPFHL-QSGXIYJFSA-N