Compound: Salicylhydroxamic acid
SMILES: O=C(NO)c1c(O)cccc1
InChIKey: HBROZNQEVUILML-UHFFFAOYSA-N
Synonyms: Salicylhydroxamic acid, N,2-Dihydroxybenzamide, 89-73-6, 2-Hydroxybenzohydroxamic acid, SHAM, Salicylohydroximic acid, 2-Hydroxybenzhydroxamic acid, O-Hydroxybenzohydroxamic acid, 2-hydroxybenzenecarbohydroxamic acid, DTXSID5075365, NSC-5088, 8Q07182D0T, NSC-193440, CHEBI:45615, RefChem:884393, DTXCID7048665, 201-934-3, Salicylohydroxamic acid, Benzamide, N,2-dihydroxy-, SHA, NSC 5088, MFCD00002110, NSC 193440, Saliaylhydroxamic acid, 2,N-Dihydroxy-benzamide, MLS000069410, CHEMBL309339, Benzamide,2-dihydroxy-, SMR000059099, SalicylhydroxaMicacid, 1-hydroxybenzene-2-carbohydroxamic acid, N-Salicylhydroxamic acid, EINECS 201-934-3, UNII-8Q07182D0T, NSC5088, N-Hydroxysalicylamide, salicyl hydroximic acid, Opera_ID_592, N,2-Dihydroxy-benzamide, Salicylic Hydroxamic Acid, N,2-Dihydroxybenzamide #, bmse000772, Oprea1_838400, Salicylhydroxamic acid, 99%, MLS001076305, SCHEMBL144849, 2-Hydroxybenzenehydroxamic acid, orb2941085, SALICYLOYLHYDROXAMIC ACID, SCHEMBL5928967, SCHEMBL21530845, benzohydroxamic acid, 2-hydroxy-, HMS2234D15, HMS3372H11, SALICYLHYDROXAMIC ACID [MI], BDBM50015089, EBC-03222, NSC193440, SBB043988, STK387225, 2-HYDROXYPHENYLHYDROXAMIC ACID, AKOS000120047, AKOS004905639, AKOS005260023, DB03819, FS-3250, FS27783, SALICYLHYDROXAMIC ACID [WHO-DD], NCGC00018115-01, NCGC00018115-02, NCGC00018115-03, HY-18721, SY046520, CS-0014188, NS00015042, S0008, ST50115655, EN300-18305, O11999, F079691, Q7404461, 2-Hydroxybenzohydroxamic acid; N,2-Dihydroxybenzamide, Z57842350, InChI=1/C7H7NO3/c9-6-4-2-1-3-5(6)7(10)8-11/h1-4,9,11H,(H,8,10
Theoretical properties:
molecular_formula: C7H7NO3
molecular_weight: 153.14 g/mol
exact_mass: 153.042593085 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 11
topological_polar_surface_area: 69.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Salicylhydroxamic acid is a hydroxamic acid that is N-hydroxybenzamide carrying a phenolic hydroxy group at position 2. It has a role as an antibacterial drug, a trypanocidal drug, an EC 3.5.1.5 (urease) inhibitor and an EC 1.11.2.2 (myeloperoxidase) inhibitor. It is a hydroxamic acid and a member of phenols.", "chebi": "A hydroxamic acid that is <em>N</em>-hydroxybenzamide carrying a phenolic hydroxy group at position 2.", "chembl": "SALICYLHYDROXAMIC ACID is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Salicylhydroxamic acid (SHA or SHAM) is a drug that is a potent and irreversible enzyme inhibitor of the urease enzyme in various bacteria and plants; it is usually used for urinary tract infections. The molecule is similar to urea but is not hydrolyzable by urease; it thus disrupts the bacteria's metabolism through competitive inhibition. It is also a trypanocidal agent.  When administered orally, it is metabolized to salicylamide, which exerts analgesic, antipyretic, and anti-inflammatory effects.\nSalicylhydroxamic acid is also a common ligand utilized in the synthesis of metallacrowns.\nIn plants, some fungi and some protists with the alternative oxidase (AOX) enzyme in the mitochondrial electron transport chain system, salicylhdroxamic acid acts as an inhibitor of the enzyme, blocking the largely uninhibited flow of electrons through AOX.  AOX acts as a \"short circuit\" of the normal electron chain, dissipating electrons with a much-decreased translocation of protons, and therefore diminished production of ATP by oxidative phosphorylation.  When AOX is blocked by SHAM, electrons are forced through the cytochrome pathway and through complex IV, allowing observation of the operation of the cytochrome pathway without AOX activity.  The AOX pathway is found to be the exclusive electron transport pathway in Trypanosoma brucei, the organism that causes African Sleeping Sickness, meaning that SHAM completely shuts down oxygen consumption by this organism."}