aristolochic acid A (CHEBI:2825)

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ChEBI Name	aristolochic acid A

ChEBI ID	CHEBI:2825

Definition	An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C17H11NO7

Net Charge

Average Mass

341.27170

Monoisotopic Mass

341.05355

InChI

InChI=1S/C17H11NO7/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20)

InChIKey

BBFQZRXNYIEMAW-UHFFFAOYSA-N

SMILES

COc1cccc2c1cc([N+]([O-])=O)c1c(cc3OCOc3c21)C(O)=O

Metabolite of Species	Details
Aristolochia (NCBI:txid12947)	See: PubMed
Aristolochia argentina (NCBI:txid158534)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. toxin Poisonous substance produced by a biological organism such as a microbe, animal or plant. nephrotoxin A poison that interferes with the function of the kidneys. (via aristolochic acids ) carcinogenic agent A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. (via aristolochic acids ) mutagen An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.

ChEBI Ontology
Outgoing	aristolochic acid A (CHEBI:2825) has role carcinogenic agent (CHEBI:50903) aristolochic acid A (CHEBI:2825) has role metabolite (CHEBI:25212) aristolochic acid A (CHEBI:2825) has role mutagen (CHEBI:25435) aristolochic acid A (CHEBI:2825) has role nephrotoxin (CHEBI:61015) aristolochic acid A (CHEBI:2825) has role toxin (CHEBI:27026) aristolochic acid A (CHEBI:2825) is a C-nitro compound (CHEBI:35716) aristolochic acid A (CHEBI:2825) is a aristolochic acids (CHEBI:194147) aristolochic acid A (CHEBI:2825) is a aromatic ether (CHEBI:35618) aristolochic acid A (CHEBI:2825) is a cyclic acetal (CHEBI:59770) aristolochic acid A (CHEBI:2825) is a monocarboxylic acid (CHEBI:25384) aristolochic acid A (CHEBI:2825) is a organic heterotetracyclic compound (CHEBI:38163)

Incoming	aristoloterpenate-I (CHEBI:132825) has functional parent aristolochic acid A (CHEBI:2825)

IUPAC Name

8-methoxy-6-nitro-2H-phenanthro[3,4-d][1,3]dioxole-5-carboxylic acid

Synonyms	Sources
3,4-methylenedioxy-8-methoxy-10-nitro-1-phenanthrenecarboxylic acid	ChemIDplus
8-methoxy-6-nitrophenanthol (3,4-d) 1,3-dioxole-5-carboxylic acid	ChemIDplus
8-methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid	IUPAC
AAA	ChEBI
Aristolochic acid	KEGG COMPOUND
aristolochic acid A	ChemIDplus
Aristolochic acid I	KEGG COMPOUND
aristolochic acid-I	ChemIDplus
aristolochin	ChemIDplus

Last Modified

05 December 2022