marimastat   Click here for help

GtoPdb Ligand ID: 5220

Synonyms: BB-2516 | BB2516
PDB Ligand
Compound class: Synthetic organic
Comment: Marimastat (BB-2516) is a broad spectrum matrix metalloprotease (MMP) inhibitor. Its MMP inhibitory action has been applied to treating cancer [2,4]. Most recently marimastat has been reported to inhibit certain snake venom metalloproteases [1], with the implication that it could be repurposed as an antidote to snake venom poisoning [5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 5
Rotatable bonds 11
Topological polar surface area 127.76
Molecular weight 331.21
XLogP 0.35
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES ONC(=O)C(C(C(=O)NC(C(C)(C)C)C(=O)NC)CC(C)C)O
Isomeric SMILES ONC(=O)[C@H]([C@H](C(=O)N[C@@H](C(C)(C)C)C(=O)NC)CC(C)C)O
InChI InChI=1S/C15H29N3O5/c1-8(2)7-9(10(19)13(21)18-23)12(20)17-11(14(22)16-6)15(3,4)5/h8-11,19,23H,7H2,1-6H3,(H,16,22)(H,17,20)(H,18,21)/t9-,10+,11-/m1/s1
InChI Key OCSMOTCMPXTDND-OUAUKWLOSA-N
Bioactivity Comments
Marimastat (BB-2516) inhibits MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7.
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
MMP9 Hs Inhibitor Inhibition 8.5 pIC50 - 2
pIC50 8.5 (IC50 3x10-9 M) [2]
MMP1 Hs Inhibitor Inhibition 8.3 pIC50 - 2
pIC50 8.3 (IC50 5x10-9 M) [2]
MMP2 Hs Inhibitor Inhibition 8.2 pIC50 - 2
pIC50 8.2 (IC50 6x10-9 M) [2]
MMP7 Hs Inhibitor Inhibition 7.8 pIC50 - 2
pIC50 7.8 (IC50 1.6x10-8 M) [2]
MMP3 Hs Inhibitor Inhibition 6.6 pIC50 - 2
pIC50 6.6 (IC50 2.3x10-7 M) [2]
Ligand mentioned in the following text fields