xanthatin   Click here for help

GtoPdb Ligand ID: 13700

Synonyms: (-)-Xanthatin | 8-epi-xanthatin
Compound class: Natural product
Comment: Xanthatin is a plant-derived sesquiterpene lactone [1]. It has been isolated from Xanthium strumarium L. Xanthatin contains an α-methylene-γ-lactone pharmacophore that is common in small molecules that have inhibitory activity at thioredoxin reductase (TrxR) enzymes, and which is crucial for interaction with the conserved selenocysteine (Sec) residue in the enzyme active site. Elevated expression of the TrxR1 isozyme is associated with therapy resistance and poor prognosis in a range of cancer types. Therefore xanthatin offers a potential anticancer mechanism.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 43.37
Molecular weight 246.3
XLogP 2.01
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
Click here for help

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/)

✖
Canonical SMILES C[C@H]1C[C@H]2[C@H](CC=C1/C=C/C(=O)C)C(=C)C(=O)O2
Isomeric SMILES C[C@H]1C[C@H]2[C@H](CC=C1/C=C/C(=O)C)C(=C)C(=O)O2
InChI InChI=1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3/b5-4+/t9-,13+,14-/m0/s1
InChI Key RBRPTFMVULVGIC-ZTIIIDENSA-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 Natural product
IUPAC Name Click here for help
(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
Synonyms Click here for help
(-)-Xanthatin | 8-epi-xanthatin
Database Links Click here for help
BindingDB Ligand 233119
CAS Registry No. 26791-73-1 (source: PubChem)
ChEBI CHEBI:10058
ChEMBL Ligand CHEMBL404466
GtoPdb PubChem SID 507750334
PubChem CID 5281511
Search Google for chemical match using the InChIKey RBRPTFMVULVGIC-ZTIIIDENSA-N
Search Google for chemicals with the same backbone RBRPTFMVULVGIC
UniChem Compound Search for chemical match using the InChIKey RBRPTFMVULVGIC-ZTIIIDENSA-N
UniChem Connectivity Search for chemical match using the InChIKey RBRPTFMVULVGIC-ZTIIIDENSA-N