Compound: alrestatin
SMILES: O=C1N(C(=O)c2cccc3c2c1ccc3)CC(=O)O
InChIKey: GCUCIFQCGJIRNT-UHFFFAOYSA-N
Synonyms: alrestatin, 51411-04-2, Alrestatine, Alrestatinum, 2-(1,3-dioxobenzo[de]isoquinolin-2-yl)acetic acid, Alrestatina, DTXSID7045655, NSC-299132, 515DHK15LG, 1,3-Dioxo-1H-benz(de)isoquinoline-2(3H)-acetate, DTXCID5025655, 2-(1,3-dioxobenzo(de)isoquinolin-2-yl)acetic acid, RefChem:555988, AY22,284, 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetic acid, Alrestatin [INN], Alrestatin free acid, (1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetic acid, (1,3-Dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetic acid, AY-22284, 1,3-Dioxo-1H-benz(de)isoquinoline-2(3H)-acetic acid, Spectrum_001449, Tocris-0485, CHEMBL63055, NSC299132, 1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid, NCGC00024613-01, F0863-0248, Alrestatino, Alrestatine [INN-French], Alrestatinum [INN-Latin], Alrestatino [INN-Spanish], CAS-51411-04-2, SR-01000597621, NSC 299132, BRN 0244370, UNII-515DHK15LG, Alrestatin?, 2-[1,3-DIOXO-1H-BENZO[DE]ISOQUINOLIN-2(3H)-YL]ACETIC ACID, GCUCIFQCGJIRNT-UHFFFAOYSA-N, 51411-04-2 (free acid), MFCD00181399, 1H-Benz[de]isoquinoline-2(3H)-aceticacid, 1,3-dioxo-, 2,3-Dihydro-1,3-dioxo-1H-benz(de)isochiolin-2-essigsaeure, SpecPlus_000666, Spectrum3_001880, Spectrum4_000089, Spectrum5_001248, ALRESTATIN [WHO-DD], BSPBio_001144, BSPBio_003360, CBDivE_001884, CBDivE_003810, CBDivE_004382, KBioGR_000358, KBioGR_000484, KBioSS_000484, KBioSS_001929, 4-21-00-05562 (Beilstein Handbook Reference), DivK1c_006762, SCHEMBL450743, orb1302006, SCHEMBL31745280, BDBM16415, KBio1_001706, KBio2_000484, KBio2_001929, KBio2_003052, KBio2_004497, KBio2_005620, KBio2_007065, KBio3_000887, KBio3_000888, KBio3_002862, 1H-Benz(de)isoquinoline-2(3H)-acetic acid, 1,3-dioxo-, Bio2_000412, Bio2_000892, HMS1362J05, HMS1792J05, HMS1990J05, HMS2092B18, HMS3266E14, HMS3403J05, HMS3411O19, HMS3675O19, HMS3866E03, Pharmakon1600-01502053, SMSSF-0061890, BCA41104, EX-A2966, HY-B1202, Tox21_110913, EBC-04218, NSC758180, s5803, SBB043177, STK395007, AKOS000143709, Tox21_110913_1, CCG-109865, CS-4830, DB02020, NSC-758180, IDI1_002167, NCGC00024613-02, NCGC00024613-03, NCGC00024613-04, NCGC00024613-06, AC-13697, AC-35588, BS-16959, SBI-0051717.P003, DB-051958, NS00069482, ST50331319, D81785, EN300-235766, AB00052267-02, AB00052267_03, AF-399/32018005, Q4735714, SR-01000597621-1, SR-01000597621-2, BRD-K35498378-001-03-8, BRD-K35498378-001-05-3, BRD-K35498378-001-06-1, BRD-K35498378-001-07-9, Z56756231, (1,3-dioxo-2-aza-2,3-dihydro-1H-phenalen-2-yl)acetic acid, 1H-BENZ(DE)ISOQUINOLINE-2(3H)ACETIC ACID, 1,3-DIOXO-, 2-{2,4-dioxo-3-azatricyclo[7.3.1.0,5,13]trideca-1(13),5,7,9,11-pentaen-3-yl}acetic acid, 2-{2,4-dioxo-3-azatricyclo[7.3.1.0;{5,13}]trideca-1(12),5,7,9(13),10-pentaen-3-yl}acetic acid
Theoretical properties:
molecular_formula: C14H9NO4
molecular_weight: 255.22 g/mol
exact_mass: 255.05315777 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 2
heavy_atom_count: 19
topological_polar_surface_area: 74.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: ALRESTATIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Alrestatin is an inhibitor of aldose reductase, an enzyme involved in the pathogenesis of complications of diabetes mellitus, including diabetic neuropathy.
Alrestat was first synthesized in 1969 and was the first aldose reductase inhibitor (ARI) with oral bioavailability to undergo clinical trials, in the late 1970s and early 1980s. Low-quality trials and a high incidence of adverse effects (particularly hepatotoxicity) led to termination of its development, and it was never in clinical use. It is structurally related to tolrestat, another ARI that was briefly marketed before being withdrawn in 1997.