ilomastat   Click here for help

GtoPdb Ligand ID: 7409

Synonyms: CS 610 | GM 6001
PDB Ligand
Compound class: Synthetic organic
Comment: Ilomastat is a broad-spectrum inhibitor of group M10 and M12 metallopeptidases.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 5
Rotatable bonds 12
Topological polar surface area 123.32
Molecular weight 388.21
XLogP 1.62
No. Lipinski's rules broken 0
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Canonical SMILES ONC(=O)CC(C(=O)NC(C(=O)NC)Cc1c[nH]c2c1cccc2)CC(C)C
Isomeric SMILES ONC(=O)C[C@H](C(=O)N[C@H](C(=O)NC)Cc1c[nH]c2c1cccc2)CC(C)C
InChI InChI=1S/C20H28N4O4/c1-12(2)8-13(10-18(25)24-28)19(26)23-17(20(27)21-3)9-14-11-22-16-7-5-4-6-15(14)16/h4-7,11-13,17,22,28H,8-10H2,1-3H3,(H,21,27)(H,23,26)(H,24,25)/t13-,17+/m1/s1
1. Johnson AR, Pavlovsky AG, Ortwine DF, Prior F, Man CF, Bornemeier DA, Banotai CA, Mueller WT, McConnell P, Yan C et al.. (2007)
Discovery and characterization of a novel inhibitor of matrix metalloprotease-13 that reduces cartilage damage in vivo without joint fibroplasia side effects.
J Biol Chem, 282 (38): 27781-91. [PMID:17623656]
2. Ma D, Wu W, Yang G, Li J, Li J, Ye Q. (2004)
Tetrahydroisoquinoline based sulfonamide hydroxamates as potent matrix metalloproteinase inhibitors.
Bioorg Med Chem Lett, 14 (1): 47-50. [PMID:14684295]
3. Oh M, Im I, Lee YJ, Kim YH, Yoon JH, Park HG, Higashiyama S, Kim YC, Park WJ. (2004)
Structure-based virtual screening and biological evaluation of potent and selective ADAM12 inhibitors.
Bioorg Med Chem Lett, 14 (24): 6071-4. [PMID:15546732]
4. Takeuchi T, Hayashi M, Tamita T, Nomura Y, Kojima N, Mitani A, Takeda T, Hitaka K, Kato Y, Kamitani M et al.. (2022)
Discovery of Aryloxyphenyl-Heptapeptide Hybrids as Potent and Selective Matrix Metalloproteinase-2 Inhibitors for the Treatment of Idiopathic Pulmonary Fibrosis.
J Med Chem, 65 (12): 8493-8510. [PMID:35687819]