Compound: N-Acetoxy-2-acetylaminofluorene
SMILES: O=C(ON(c1cc2c(-c3ccccc3C2)cc1)C(=O)C)C
InChIKey: NFOMHWALMFWNAQ-UHFFFAOYSA-N
Synonyms: N-Acetoxy-2-acetylaminofluorene, ACETOXYACETYLAMINOFLUORENE, 6098-44-8, NAAAF, Acetoxyacetamidofluorene, N-Acetoxy-2-fluorenylacetamide, 2-Acetoxyacetylaminofluorene, N-Acetoxy-N-2-fluorenylacetamide, Acetamide, N-(acetyloxy)-N-9H-fluoren-2-yl-, N-Acetoxy-N-acetyl-2-aminofluorene, N-(Fluoren-2-yl)acetohydroxamic acetate, N-Acetoxy-2-acetaminofluorene, N-(Fluoren-2-yl)acetohydroxamic acetamide, Acetic acid, ester with N-(fluoren-2-yl)acetohydroxamic acid, N-(Acetoxy)-N-9H-fluoren-2-ylacetamide, Acetic acid, (N-acetyl-N-(2-fluorenyl)amino) ester, DTXSID90209828, Acetoxyfluorenylacetamide, Acetic acid, [N-acetyl-N-(2-fluorenyl)amino] ester, N Acetoxy 2 acetylaminofluorene, N Acetoxy N acetyl 2 aminofluorene, RefChem:109026, DTXCID40132319, Acetoxy AAF, N-Acetoxy-2-acetamidofluorene, NA-AAF, NSC 163627, N-Acetoxy-N-(9H-fluoren-2-yl)acetamide, 2-(Acetoxyacetylamino)fluorene, N-(Acetyloxy)-N-9H-fluoren-2-ylacetamide, Acetamide, N-(acetoxy)-N-9H-fluoren-2-yl-, Hydroxylamine, N,O-diacetyl-N-fluoren-2-yl-, CCRIS 729, N-Acetoxy-N-acetyl-aminofluorene, N-Acetoxy-2-acetyl aminofluorene, NFOMHWALMFWNAQ-UHFFFAOYSA-N, BRN 2222410, [acetyl(9H-fluoren-2-yl)amino] acetate, SCHEMBL73231, CHEMBL85327, CHEBI:76331, GLXC-10389, N-Acetyl-N-acetoxy-2-aminofluorene, NSC163627, NSC-163627, WLN: L B656 HHJ ENV1&OV1, Hydroxylamine,O-diacetyl-N-fluoren-2-yl-, N-acetyloxy-N-(9H-fluoren-2-yl)acetamide, N-(Acetyloxy)-N-(9H-fluoren-2-yl)acetamide, Q4673285
Theoretical properties:
molecular_formula: C17H15NO3
molecular_weight: 281.30 g/mol
exact_mass: 281.10519334 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 21
topological_polar_surface_area: 46.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "N-acetoxy-2-acetamidofluorene is a 2-acetamidofluorene compound in which the parent 2-acetamidofluorene is substituted on nitrogen by an acetoxy group. It has a role as a mutagen and a carcinogenic agent.", "chebi": "A 2-acetamidofluorene compound in which the parent 2-acetamidofluorene is substituted on nitrogen by an acetoxy group.", "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "2-Acetylaminofluorene (AAF, 2-AAF) is a carcinogenic and mutagenic derivative of fluorene.  It is used as a biochemical tool in the study of carcinogenesis. It induces tumors in a number of species in the liver, bladder and kidney. The metabolism of this compound in the body by means of biotransformation reactions is the key to its carcinogenicity. 2-AAF is a substrate for cytochrome P-450 (CYP) enzyme, which is a part of a super family found in almost all organisms. This reaction results in the formation of hydroxyacetylaminofluorene which is a proximal carcinogen and is more potent than the parent molecule. The N-hydroxy metabolite undergoes several enzymatic and non-enzymatic rearrangements. It can be O-acetylated by cytosolic N-acetyltransferase enzyme to yield N-acetyl-N-acetoxyaminofluorene. This intermediate can spontaneously rearrange to form the arylamidonium ion and a carbonium ion which can interact directly with DNA to produce DNA adducts. In addition to esterification by acetylation, the N-hydroxy derivative can be O-sulfated by cytosolic sulfur transferase enzyme giving rise to the N-acetyl-N-sulfoxy product.\nIn addition, the cytosolic N,O-aryl hydroxamic acid acyltransferase enzyme catalyzes the transfer of the acetyl group from the N atom of the N-OH-2-AAF to the O atom of the N-OH group to produce N-acetoxy-2-aminofluorene (N-OH-2-AF). This reactive metabolite spontaneously decomposes to form a nitrenium ion which will also react with DNA. However, the product of this latter reaction is the deacetylated aminofluorene adduct. The interconversion of amide and amine metabolites of 2-AAF can further occur via the microsomal enzyme deacetylase producing the N-hydroxy metabolite of the amine derivative. Subsequent esterification of the aryl hydroxylamine by sulfur transferase yields the sulfate ester which also spontaneously decompose to form nitrenium ion. The reactive nitrenium, carbonium and arylamidonium ion metabolites of 2-AAF react with the nucleophilic groups in DNA, proteins and endogenous thiols such as glutathione. Other metabolites such as the N,O-glucuronide, although not directly activated products, can be important in the carcinogenic process because they are capable of degradation to proximal N-hydroxy metabolites. This metabolite is presumed to be involved in formation of bladder tumors. The mechanism for this is thought to involve degradation of glucuronide in the bladder due to acidic pH of urine."}