staurosporine   Click here for help

GtoPdb Ligand ID: 346

Synonyms: (+)-staurosporine | antibiotic 230 | antibiotic AM-2282
PDB Ligand
Comment: Staurosporine is a non-specific, ATP-competitive inhibitor of protein kinase C (PKC) isolated from a Streptomyces strain [10]. It inhibits all PKC enzyme isoforms [2,13], but has a more potent inhibitory effect on PKCs associated with the cell membrane compared to cytosolic PKCs.
Staurosporine analogues such as midostaurin and 7-hydroxystaurosporine are being investigated as therapeutics.
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 5
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 69.45
Molecular weight 466.2
XLogP 6.05
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES CNC1CC2OC(C1OC)(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3CNC1=O
Isomeric SMILES CN[C@@H]1C[C@H]2O[C@]([C@@H]1OC)(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3CNC1=O
InChI InChI=1S/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20-,26-,28+/m1/s1
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
Synonyms Click here for help
(+)-staurosporine | antibiotic 230 | antibiotic AM-2282
Database Links Click here for help
Specialist databases
GPCRdb Ligand staurosporine
Other databases
BindingDB Ligand 2579
CAS Registry No. 62996-74-1
ChEMBL Ligand CHEMBL388978
DrugBank Ligand DB02010
GtoPdb PubChem SID 135652717
PubChem CID 44259
Search Google for chemical match using the InChIKey HKSZLNNOFSGOKW-FYTWVXJKSA-N
Search Google for chemicals with the same backbone HKSZLNNOFSGOKW
SynPHARM 81547 (in complex with death associated protein kinase 1)
81546 (in complex with mitogen-activated protein kinase kinase 6)
UniChem Compound Search for chemical match using the InChIKey HKSZLNNOFSGOKW-FYTWVXJKSA-N
UniChem Connectivity Search for chemical match using the InChIKey HKSZLNNOFSGOKW-FYTWVXJKSA-N
Wikipedia Staurosporine

Product suppliers

View disclaimer

Staurosporine (links to external site)
Cat. No. 1285