Aristolochic acid

Aristolochic acid I
Names
	Preferred IUPAC name 8-Methoxy-6-nitro-2H-phenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
	Other names Aristinic acid; Aristolochia yellow; Aristolochic acid A; Aristolochin;Aristolochine; Descresept; Tardolyt;TR 1736
Identifiers
CAS Number	313-67-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL93353 ;
ChemSpider	2149 ;
KEGG	C08469 ;
PubChem CID	2236;
UNII	94218WFP5T ;
	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) Key: BBFQZRXNYIEMAW-UHFFFAOYSA-N ; InChI=1/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) Key: BBFQZRXNYIEMAW-UHFFFAOYAG;
	SMILES [O-][N+](=O)c1cc4c(c2c1c(C(=O)O)cc3OCOc23)cccc4OC;
Properties
Chemical formula	C17H11NO7
Molar mass	341.275 g·mol−1
Appearance	yellow powder
Melting point	260 to 265 °C (500 to 509 °F; 533 to 538 K)
Solubility in water	Slightly soluble
Hazards
NFPA 704 (fire diamond)	2 1 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Aristolochic acids (English: /əˌrɪstəˈloʊkɪk/) are a family of carcinogenic, mutagenic, and nephrotoxic phytochemicals commonly found in the flowering plant family Aristolochiaceae (birthworts). Aristolochic acid (AA) I is the most abundant one.^[1] The family Aristolochiaceae includes the genera Aristolochia and Asarum (wild ginger), which are commonly used in Chinese herbal medicine.^[2]^[3] Although these compounds are widely associated with kidney problems, liver and urothelial cancers, the use of AA-containing plants for medicinal purposes has a long history. The FDA has issued warnings regarding consumption of AA-containing supplements.

^ Wu, Tian-Shung; et al. (2005). "Chemical constituents and pharmacology of Aristolochia species". In Rahman, Atta-ur (ed.). Studies in Natural Products Chemistry: Bioactive Natural Products (Part L). Gulf Professional Publishing. p. 863. ISBN 978-0-444-52171-2.
^ Heinrich M, Chan J, Wanke S, Neinhuis C, Simmonds MS (August 2009). "Local uses of Aristolochia species and content of nephrotoxic aristolochic acid 1 and 2--a global assessment based on bibliographic sources". J Ethnopharmacol. 125 (1): 108–44. doi:10.1016/j.jep.2009.05.028. PMID 19505558.
^ Nolin, Thomas D. & Himmelfarb, Jonathan (2010). "Mechanisms of drug-induced nephrotoxicity". In Uetrecht, Jack (ed.). Adverse Drug Reactions. Springer. p. 123. ISBN 978-3-642-00662-3.

[1] Wu, Tian-Shung; et al. (2005). "Chemical constituents and pharmacology of Aristolochia species". In Rahman, Atta-ur (ed.). Studies in Natural Products Chemistry: Bioactive Natural Products (Part L). Gulf Professional Publishing. p. 863. ISBN 978-0-444-52171-2.

[2] Heinrich M, Chan J, Wanke S, Neinhuis C, Simmonds MS (August 2009). "Local uses of Aristolochia species and content of nephrotoxic aristolochic acid 1 and 2--a global assessment based on bibliographic sources". J Ethnopharmacol. 125 (1): 108–44. doi:10.1016/j.jep.2009.05.028. PMID 19505558.

[3] Nolin, Thomas D. & Himmelfarb, Jonathan (2010). "Mechanisms of drug-induced nephrotoxicity". In Uetrecht, Jack (ed.). Adverse Drug Reactions. Springer. p. 123. ISBN 978-3-642-00662-3.

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