batimastat   Click here for help

GtoPdb Ligand ID: 5145

Synonyms: BB 94 | BB-94 | BB94
PDB Ligand
Compound class: Synthetic organic
Comment: Batimastat (BB-94) is a broad-spectrum matrix metalloprotease (MMP) inhibitor. It inhibits MMPs by binding the zinc ion in the active site of the enzymes.
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 4
Rotatable bonds 15
Topological polar surface area 161.07
Molecular weight 477.18
XLogP 2.94
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES CNC(=O)C(NC(=O)C(C(C(=O)NO)CSc1cccs1)CC(C)C)Cc1ccccc1
Isomeric SMILES CNC(=O)[C@@H](NC(=O)[C@@H]([C@@H](C(=O)NO)CSc1cccs1)CC(C)C)Cc1ccccc1
InChI InChI=1S/C23H31N3O4S2/c1-15(2)12-17(18(22(28)26-30)14-32-20-10-7-11-31-20)21(27)25-19(23(29)24-3)13-16-8-5-4-6-9-16/h4-11,15,17-19,30H,12-14H2,1-3H3,(H,24,29)(H,25,27)(H,26,28)/t17-,18+,19+/m1/s1
Bioactivity Comments
Batimastat (≤10 ng/ml) inhibits at least 50% of MMP activity in vitro. In vivo, it delays ascites accumulation and increases survival in mice with human ovarian tumour xenografts [5].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
MMP1 Hs Inhibitor Inhibition 9.3 pKi - 2
pKi 9.3 (Ki 5x10-10 M) [2]
MMP3 Hs Inhibitor Inhibition 9.2 pIC50 - 6
pIC50 9.2 (IC50 6.5x10-10 M) [6]
MMP1 Hs Inhibitor Inhibition 9.0 pIC50 - 3
pIC50 9.0 (IC50 9.9x10-10 M) [3]
MMP13 Hs Inhibitor Inhibition 8.3 pIC50 - 3
pIC50 8.3 (IC50 5x10-9 M) [3]
Ligand mentioned in the following text fields