ischemin   Click here for help

GtoPdb Ligand ID: 7506

Synonyms: MS120
Compound class: Synthetic organic
Comment: Ischemin binds reversibly to the bromodomain of CREB-binding protein (CBP) and blocks CBP association with binding partners [1]. This results in inhibition of transcription functions performed by p53.

Note that ischemin is represented in different ways by different online resources and suppliers. We show the molecule with a specified E bond as this is the form used in the associated PDB solution NMR structure (shown on the CBP page). Whereas, the chemical description in [1] leaves this bond unspecified (see PubChem CID 73010922).
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 130.23
Molecular weight 335.09
XLogP 1.13
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES NC1=CC(=O)C(=CC1=NNc1cc(c(cc1C)C)S(=O)(=O)O)C
Isomeric SMILES NC1=CC(=O)C(=C/C/1=N\Nc1cc(c(cc1C)C)S(=O)(=O)O)C
InChI InChI=1S/C15H17N3O4S/c1-8-4-10(3)15(23(20,21)22)7-12(8)17-18-13-5-9(2)14(19)6-11(13)16/h4-7,17H,16H2,1-3H3,(H,20,21,22)/b18-13+
InChI Key WGEVKJVUKOELFY-QGOAFFKASA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-[(2E)-2-(2-amino-5-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)hydrazinyl]-2,4-dimethylbenzenesulfonic acid
Synonyms Click here for help
MS120
Database Links Click here for help
CAS Registry No. 1357059-00-7 (source: Scifinder)
GtoPdb PubChem SID 187051808
PubChem CID 49837845
Search Google for chemical match using the InChIKey WGEVKJVUKOELFY-QGOAFFKASA-N
Search Google for chemicals with the same backbone WGEVKJVUKOELFY
Search UniChem for chemical match using the InChIKey WGEVKJVUKOELFY-QGOAFFKASA-N
Search UniChem for chemicals with the same backbone WGEVKJVUKOELFY
SynPHARM 79896 (in complex with CREB binding protein)