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Compound Summary

General Compound Information

Aristolochic acid

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Description

Aristolochic acid is 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. It has a role as a nephrotoxin, a carcinogenic agent, a mutagen, a toxin and a metabolite. It is a monocarboxylic acid, a C-nitro compound, a cyclic acetal, an organic heterotetracyclic compound and an aromatic ether.

Synonyms

Aristolochic acid; Aristolochic acid A; 313-67-7; Aristolochic acid I; Aristolochin;

Tardolyt;Aristolochic acid-I;ARISTOLOCHINE;TR 1736;NSC-50413;8-Methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid;NSC11926;3,4-Methylenedioxy-8-methoxy-10-nitro-1-phenanthrenecarboxylic acid;NSC50413;Birthwort;8-Methoxy-3,4-methylenedioxy-10-nitrophenanthrene-1-carboxylic acid;8-Methoxy-6-nitrophenanthol (3,4-d) 1,3-dioxole-5-carboxylic acid;CHEMBL93353;MLS002702976;CHEBI:2825;Aristolochic acid I;TR 1736;94218WFP5T;Phenanthro(3,4-d)-1,3-dioxole-5-carboxylic acid, 8-methoxy-6-nitro-;Phenanthro[3,4-d]-1,3-dioxole-5-carboxylic acid, 8-methoxy-6-nitro-;NSC-11926;8-methoxy-6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid;Aristolochiazaeure;8-methoxy-6-nitro-naphtho[1,2-e][1,3]benzodioxole-5-carboxylic acid;8-METHOXY-6-NITROPHENANTHROL(3,4-D)-1,3-DIOXIDE-5-CARBOXYLIC ACID;SMR001562128;Aristolochic acid 1;CCRIS 1544;SR-05000002369;EINECS 206-238-3;NSC 11926;NSC 50413;BRN 0345159;Aristolochia;Phenanthro[3,3-dioxole-5-carboxylic acid, 8-methoxy-6-nitro-;UNII-94218WFP5T;AristolochicacidA;aris-tolochic acid;GOQ;Aristolochic-acid-A;MFCD00004996;ARISTOLOCHIA A;Spectrum_001156;SpecPlus_000448;8-Methoxy-3,4-methylendioxxy-10-nitro-1-phenanthrencarbonsaeure;8-methoxy-6-nitrophenanthro(3,4-d)-1,3-dioxole-5-carboxylic acid;Spectrum2_000822;Spectrum3_001114;Spectrum4_001952;Spectrum5_000729;Aristolochic acid A,(S);ZINC52;NCIMech_000812;Aristolochic acid I, powder;BSPBio_001440;BSPBio_002848;KBioGR_000160;KBioGR_002387;KBioSS_000160;KBioSS_001636;MLS002695974;DivK1c_006544;SCHEMBL166284;SPECTRUM1502233;SPBio_000743;ARISTOLOCHIC ACID [MI];ARISTOLOCHIC ACID [IARC];DTXSID0040969;KBio1_001488;KBio2_000160;KBio2_001636;KBio2_002728;KBio2_004204;KBio2_005296;KBio2_006772;KBio3_000319;KBio3_000320;KBio3_002068;Bio1_000418;Bio1_000907;Bio1_001396;Bio2_000160;Bio2_000640;HMS1361H22;HMS1791H22;HMS1989H22;HMS3402H22;ARISTOLOCHIC ACID [WHO-DD];HY-N0510;TNP00273;8-methoxy-6-nitro-naphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid;BDBM50306855;CCG-35796;CCG-36162;s9193;Mixture of Aristolochic Acid A and B;AKOS015896751;TR-1736;IDI1_033910;2-Naphthyl Pyrovalerone-d8 Hydrochloride;NCGC00017334-01;NCGC00017334-02;NCGC00017334-03;NCGC00017334-04;NCGC00017334-05;NCGC00017334-06;NCGC00017334-07;NCGC00095981-01;NCGC00095981-02;NCGC00095981-03;NCGC00095981-04;NCGC00095981-05;1246815-48-4;AC-34489;BS-16911;NCI60_000460;XA167153;DB-048017;CS-0009050;FT-0602867;C08469;ARISTOLOCHIC ACID, PLANTS CONTAINING [IARC];Q-100394;SR-05000002369-2;SR-05000002369-3;Q21099362;Aristolochia, European Pharmacopoeia (EP) Reference Standard;8-Methoxy-6-nitro-phenanthro[3,4-d][1,3]dioxole-5-carboxylic acid;Aristolochic acid I, European Pharmacopoeia (EP) Reference Standard;8-Methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid #;Phenanthro[3,4-d]-1,3-dioxole-5-carbocylic acid, 8-methoxy-6-nitro-;

FlavorDB ID

57

PUBCHEM ID

2236

Molecular Weight

341.27

Molecular Formula

C17H11NO7

Openeye Can Smiles

COC1=CC=CC2=C3C(=C(C=C21)[N+](=O)[O-])C(=CC4=C3OCO4)C(=O)O

IUPAC Inchikey

BBFQZRXNYIEMAW-UHFFFAOYSA-N

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Compound Classification

Classification (Parent Nodes)

ClassyFire Ontology

Compound Quality

Quality information of this compound is not available!

Compound Toxicity and Food Additive Safety (OFAS)

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database

Receptors

Receptor	REFERENCE	EC50 [µM]	Effective Concentration [µM]
TAS2R4	details	Activated	Activated
TAS2R8	details	Activated	Activated
TAS2R14	details	1.90	0.10
TAS2R31	details	0.46	0.03
TAS2R43	details	0.08	1100.00

GC-MS Consensus Spectra

GC-MS Consensus Spectra information of this compound is not available!