Compound: Ilomastat
SMILES: O=C(NC)[C@@H](NC(=O)[C@@H](CC(=O)NO)CC(C)C)Cc1c2c(cccc2)[nH]c1
InChIKey: NITYDPDXAAFEIT-DYVFJYSZSA-N
Synonyms: Ilomastat, 142880-36-2, Galardin, GM6001, GM 6001, CS 610, GM-6001, DTXSID0046353, CS-610, I0403ML141, (R)-N(sup 1)-Hydroxy-N-((S)-2-indol-3-yl-1-(methylcarbamoyl)ethyl)-2-isobutylsuccinamide, (S-(R*,S*))-N(sup 4)-Hydroxy-N(sup 1)-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylopropyl)butanediamide, DTXCID8026353, CHEBI:137236, ilomastatum, (2R)-N'-hydroxy-N-((2S)-3-(1H-indol-3-yl)-1-methylamino-1-oxopropan-2-yl)-2-(2-methylpropyl)butanediamide, (2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-methylamino-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide, RefChem:790596, N'-hydroxy-N-((S)-2-indol-3-yl-1-(methylcarbamoyl)ethyl)-2-isobutylsuccinamide, (2R)-N'-hydroxy-N-((1S)-2-(1H-indol-3-yl)-1-(methylcarbamoyl)ethyl)-2-(2-methylpropyl)butanediamide, Butanediamide, N4-hydroxy-N1-((1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylpropyl)-,(2R)-, Illomastat, (R)-N1-((S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl)-N4-hydroxy-2-isobutylsuccinamide, Ilomastat (GM6001, Galardin), MFCD00917040, CHEMBL19611, (2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide, Ilomastat [USAN], NCGC00163450-02, 3-(N-HYDROXYCARBOXAMIDO)-2-ISOBUTYLPROPANOYL-TRP-METHYLAMIDE, Galardin MPI, (2R)-2-[2-(hydroxyamino)-2-oxo-ethyl]-N-[(1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxo-ethyl]-4-methyl-pentanamide, Ilomastat (USAN/INN), Ilomastat [USAN:INN], UNII-I0403ML141, 4pkw, GM6, ILOMASTAT [INN], Ilomastat; GM-6001, GM6001;Galardin;Ilomastat, CBiol_001883, SCHEMBL35303, BSPBio_001079, KBioGR_000419, KBioSS_000419, GTPL7409, orb1305084, SCHEMBL29412562, BCBcMAP01_000057, KBio2_000419, KBio2_002987, KBio2_005555, KBio3_000797, KBio3_000798, EX-A765, GM6001 (galardin, ilomastat)?, BDBM234334, Bio1_000169, Bio1_000658, Bio1_001147, Bio2_000370, Bio2_000850, HMS1362E21, HMS1792E21, HMS1990E21, HMS3403E21, SFA88036, Tox21_112055, BDBM50062351, MFCD03453614, NSC727632, s7157, AKOS016355429, CCG-207857, CS-1701, DB02255, NSC-727632, (R)-N4-Hydroxy-N1-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide, IDI1_002125, SMP2_000212, NCGC00163450-01, NCGC00163450-03, NCGC00163450-04, AS-56152, Butanediamide, N4-hydroxy-N1-((1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylpropyl)-, (2R)-, Butanediamide, N4-hydroxy-N1-(1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylpropyl)-, (S-(R*,S*))-, DA-73817, HY-15768, CAS-142880-36-2, NS00069181, SW218170-2, A11456, D03793, BRD-K51662849-001-02-1, BRD-K51662849-001-05-4, BRD-K51662849-001-08-8, GM 6001 - CAS 142880-36-2, (R)-N*4*-Hydroxy-N*1*-[2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide, (2R)-N(4)-hydroxy-N(1)-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide, (2R)-N~4~-hydroxy-N~1~-[(1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl]-2-(2-methylpropyl)butanediamide, (2R)-N~4~-Hydroxy-N~1~-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide, (R)-N*4*-Hydroxy-N*1*-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide
Theoretical properties:
molecular_formula: C20H28N4O4
molecular_weight: 388.5 g/mol
exact_mass: 388.21105539 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 9
heavy_atom_count: 28
topological_polar_surface_area: 123 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Ilomastat is an N-acyl-amino acid obtained by formal condensation of the carboxy group of (2R)-2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the amino group of N-methyl-L-tryptophanamide. A cell permeable broad-spectrum matrix metalloproteinase (MMP) inhibitor. It has a role as an antibacterial agent, an antineoplastic agent, a neuroprotective agent, an anti-inflammatory agent and an EC 3.4.24.24 (gelatinase A) inhibitor. It is a hydroxamic acid, a L-tryptophan derivative and a N-acyl-amino acid.
chebi: An <em>N</em>-acyl-amino acid obtained by formal condensation of the carboxy group of (2<i>R</i>)-2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the amino group of <em>N</em>-methyl-<small>L</small>-tryptophanamide. A cell permeable broad-spectrum matrix metalloproteinase (MMP) inhibitor
chembl: ILOMASTAT is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Ilomastat (INN; development code GM6001; proprietary name Galardin) is a broad-spectrum matrix metalloproteinase inhibitor.
This chemotherapy agent is considered to have application in skincare products for its antiaging properties.
Ilomastat is a member of the hydroxamic acid class of reversible metallopeptidase inhibitors. The anionic state of the hydroxamic acid group forms a bidentate complex with the active site zinc.
Examples of enzymes that ilomastat inhibit include rabbit MMP9, thermolysin, peptide deformylase, and anthrax lethal factor endopeptidase (LF) produced by the bacterium Bacillus anthracis.