cis-JB253   Click here for help

GtoPdb Ligand ID: 7787

Compound class: Synthetic organic
Comment: cis-JB253 is described in [1]. The structure is based upon that of the diabetes sulfonylurea drug glimepiride. This compound is formed from trans-JB253 upon photoisomerization using blue light. This isomerization process is reversible. The molecule is active in the cis-state, increasing insulin production from pancreatic B-cells in vitro. It is postulated that this type of photoswitchable compound could in the future, allow better control of blood glucose in diabetic patients [1].
Note that the PubChem CID we link to does not specify the cis-trans state of the compound.
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 8
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 111.61
Molecular weight 457.21
XLogP 6.26
No. Lipinski's rules broken 1

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 CCN(c1ccc(cc1)N=Nc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCCCC1)CC
Isomeric SMILES CCN(c1ccc(cc1)/N=N\c1ccc(cc1)S(=O)(=O)NC(=O)NC1CCCCC1)CC
InChI InChI=1S/C23H31N5O3S/c1-3-28(4-2)21-14-10-19(11-15-21)25-26-20-12-16-22(17-13-20)32(30,31)27-23(29)24-18-8-6-5-7-9-18/h10-18H,3-9H2,1-2H3,(H2,24,27,29)/b26-25-
InChI Key FCHDFDWESRUUDK-QPLCGJKRSA-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
IUPAC Name Click here for help
1-cyclohexyl-3-{4-[(Z)-2-[4-(diethylamino)phenyl]diazen-1-yl]benzenesulfonyl}urea
Database Links Click here for help
GtoPdb PubChem SID 223366119
PubChem CID 78060683
Search Google for chemical match using the InChIKey FCHDFDWESRUUDK-QPLCGJKRSA-N
Search Google for chemicals with the same backbone FCHDFDWESRUUDK
UniChem Compound Search for chemical match using the InChIKey FCHDFDWESRUUDK-QPLCGJKRSA-N
UniChem Connectivity Search for chemical match using the InChIKey FCHDFDWESRUUDK-QPLCGJKRSA-N