CHEBI:2825 - aristolochic acid

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ChEBI Name aristolochic acid
ChEBI ID CHEBI:2825
Definition A monocarboxylic 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 0
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.
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.
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.
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ChEBI Ontology
Outgoing aristolochic acid (CHEBI:2825) has role carcinogenic agent (CHEBI:50903)
aristolochic acid (CHEBI:2825) has role metabolite (CHEBI:25212)
aristolochic acid (CHEBI:2825) has role mutagen (CHEBI:25435)
aristolochic acid (CHEBI:2825) has role nephrotoxin (CHEBI:61015)
aristolochic acid (CHEBI:2825) has role toxin (CHEBI:27026)
aristolochic acid (CHEBI:2825) is a C-nitro compound (CHEBI:35716)
aristolochic acid (CHEBI:2825) is a aromatic ether (CHEBI:35618)
aristolochic acid (CHEBI:2825) is a cyclic acetal (CHEBI:59770)
aristolochic acid (CHEBI:2825) is a monocarboxylic acid (CHEBI:25384)
aristolochic acid (CHEBI:2825) is a organic heterotetracyclic compound (CHEBI:38163)
Incoming aristoloterpenate-I (CHEBI:132825) has functional parent aristolochic acid (CHEBI:2825)
IUPAC Name
8-methoxy-6-nitrophenanthro[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
Aristolochic acid KEGG COMPOUND
aristolochic acid A ChemIDplus
Aristolochic acid I KEGG COMPOUND
aristolochic acid-I ChemIDplus
aristolochin ChemIDplus
Manual Xrefs Databases
Aristolochic_acid Wikipedia
C00001526 KNApSAcK
C00027516 KNApSAcK
C08469 KEGG COMPOUND
LSM-2373 LINCS
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Registry Numbers Types Sources
313-67-7 CAS Registry Number ChemIDplus
345159 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
21558304 PubMed citation Europe PMC
21719716 PubMed citation Europe PMC
22071594 PubMed citation Europe PMC
22118289 PubMed citation Europe PMC
22126455 PubMed citation Europe PMC
22245565 PubMed citation Europe PMC
22373701 PubMed citation Europe PMC
Last Modified
24 January 2017