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aristolochic acid

Go to external page http://purl.obolibrary.org/obo/CHEBI_2825

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.

Term info

Label

aristolochic acid

Synonyms
  • 8-methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
  • Aristolochic acid
database cross reference
Subsets

3_STAR

IUPAC NAME
8-methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid [ IUPAC ]

charge

0

formula

C17H11NO7

has obo namespace

chebi_ontology

has related synonym

Aristolochic acid I, aristolochin, 3,4-methylenedioxy-8-methoxy-10-nitro-1-phenanthrenecarboxylic acid, aristolochic acid-I, 8-methoxy-6-nitrophenanthol (3,4-d) 1,3-dioxole-5-carboxylic acid, aristolochic acid A

id

CHEBI:2825

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

mass

341.27170

monoisotopicmass

341.05355

smiles

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