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.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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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.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

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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
SMILES / InChI / InChIKey
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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.

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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
InChI Key XFILPEOLDIKJHX-QYZOEREBSA-N
References
1. Beattie GJ, Smyth JF. (1998)
Phase I study of intraperitoneal metalloproteinase inhibitor BB94 in patients with malignant ascites.
Clin Cancer Res, 4 (8): 1899-902. [PMID:9717817]
2. Castelhano AL, Billedeau R, Dewdney N, Donnelly S, Horne S, Kurz LJ, Liak T, Martin R, Uppington R, Zhengyu Yuan et al.. (1995)
Novel indolactam-based inhibitors of matrix metalloproteinases.
Bioorg Med Chem Lett, 5: 1415-1420. DOI: 10.1016/0960-894X(95)00233-J
3. Fray MJ, Dickinson RP, Huggins JP, Occleston NL. (2003)
A potent, selective inhibitor of matrix metalloproteinase-3 for the topical treatment of chronic dermal ulcers.
J Med Chem, 46 (16): 3514-25. [PMID:12877590]
4. Parsons SL, Watson SA, Steele RJ. (1997)
Phase I/II trial of batimastat, a matrix metalloproteinase inhibitor, in patients with malignant ascites.
Eur J Surg Oncol, 23 (6): 526-31. [PMID:9484924]
5. Wojtowicz-Praga S, Low J, Marshall J, Ness E, Dickson R, Barter J, Sale M, McCann P, Moore J, Cole A et al.. (1996)
Phase I trial of a novel matrix metalloproteinase inhibitor batimastat (BB-94) in patients with advanced cancer.
Invest New Drugs, 14 (2): 193-202. [PMID:8913840]
6. Yamamoto M, Tsujishita H, Hori N, Ohishi Y, Inoue S, Ikeda S, Okada Y. (1998)
Inhibition of membrane-type 1 matrix metalloproteinase by hydroxamate inhibitors: an examination of the subsite pocket.
J Med Chem, 41 (8): 1209-17. [PMID:9548812]