ContaminantDB: Aristolochic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:17:15 UTC

Update Date

2026-03-26 21:41:47 UTC

Accession Number

CHEM003073

Identification

Common Name

Aristolochic acid

Class

Small Molecule

Description

Aristolochic acids are a family of carcinogenic, mutagenic, and nephrotoxic compounds commonly found in the Aristolochiaceae family of plants, including Aristolochia and Asarum (wild ginger), which are commonly used in Chinese herbal medicine. Aristolochic acid I is the most abundant of the aristolochic acids and is found in almost all Aristolochia species. Aristolochic acids are often accompanied by aristolactams.

Contaminant Sources

IARC Carcinogens Group 1
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Ester
Ether
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4-Methylenedioxy-8-methoxy-10-nitro-1-phenanthrenecarboxylic acid	ChEBI
8-Methoxy-6-nitrophenanthol (3,4-D) 1,3-dioxole-5-carboxylic acid	ChEBI
Aristolochic acid a	ChEBI
Aristolochic acid I	ChEBI
Aristolochic acid-I	ChEBI
Aristolochin	ChEBI
3,4-Methylenedioxy-8-methoxy-10-nitro-1-phenanthrenecarboxylate	Generator
8-Methoxy-6-nitrophenanthol (3,4-D) 1,3-dioxole-5-carboxylate	Generator
Aristolochate a	Generator
Aristolochate I	Generator
Aristolochate-I	Generator
Aristolochate	Generator
Aristolochic acid I, sodium salt	MeSH
8-Methoxy-6-nitrophenanthro(3,4-D)-1,3-dioxole-5-carboxylic acid	MeSH
Tardolyt	MeSH
Sodium aristolochate	MeSH

Chemical Formula

C₁₇H₁₁NO₇

Average Molecular Mass

341.272 g/mol

Monoisotopic Mass

341.054 g/mol

CAS Registry Number

313-67-7

IUPAC Name

6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1,3,5,7,9,11,13(17)-heptaene-11-carboxylic acid

Traditional Name

birthwort

SMILES

COC1=CC=CC2=C3C4=C(OCO4)C=C(C(O)=O)C3=C(C=C12)N(=O)=O

InChI Identifier

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)

InChI Key

BBFQZRXNYIEMAW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aristolochic acids and derivatives. These are organic heterocyclic compounds with a structure characterized by a nitrophenanthro[3,4-d][1,3]dioxole ring system substituted at position 5, 6, and 8 by a carboxyl group (or a derivative thereof), a nitro group, and a methoxy group, respectively.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Aristolochic acids and derivatives

Direct Parent

Aristolochic acids and derivatives

Alternative Parents

Substituents

Aristolochic acid or derivatives
1-naphthalenecarboxylic acid
1-naphthalenecarboxylic acid or derivatives
1-nitronaphthalene
2-nitronaphthalene
Naphthalene
Benzodioxole
Nitroaromatic compound
Anisole
Alkyl aryl ether
Organic nitro compound
C-nitro compound
Acetal
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-nitro compound (CHEBI:2825 )
monocarboxylic acid (CHEBI:2825 )
cyclic acetal (CHEBI:2825 )
phenanthrenes (CHEBI:2825 )
Isoquinoline alkaloids (C08469 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Acrosome
Actin Cytoskeleton
Actin Filament
Apical Membrane
Cell junction
Cell surface
Cytoskeleton
Cytosol
Endoplasmic reticulum
Extracellular
Extracellular matrix
Intermediate Filament
Lysosome
Membrane
Microsome
Microtubule
Mitochondrial Intermembrane Space
Mitochondrial Membrane
Mitochondrion
Peroxisome
Plasma Membrane
Sarcoplasmic Reticulum

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Apoptosis	Not Available	map04210
Endocytosis	Not Available	map04144
Butyrophenones	Not Available	Not Available
Cell cycle	Not Available	map04110
Metabolic Pathways	Not Available	Not Available
Eicosanoids	Not Available	Not Available
Glutathione Metabolism	SMP00015	map00480
Dna replication	Not Available	map03030
Arachidonic Acid Metabolism	SMP00075	map00590

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	2.69	ALOGPS
logP	3.02	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	110.81 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.77 m³·mol⁻¹	ChemAxon
Polarizability	32.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01oy-3097000000-da70a568598192c4149d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-192503bd944b4098f295	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0019000000-36268a06fdb878508480	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-022d-0059000000-e1c393e1f4dcf97ab02c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-ec56c61ed56ce4fdd6d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-0f6cf8b2fee975ef3311	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0016-2093000000-237334dcb4e6c37619ae	Spectrum

Toxicity Profile

Route of Exposure

Oral

Mechanism of Toxicity

The carcinogenic and mutagenic effects associated with the binding of metabolites of ingested aristolochic acid (AA) to DNA have been extensively described in vitro and in vivo, resulting in the classification of AA as a genotoxic carcinogen. AA-derived DNA adducts in renal cortical and urothelial tumor tissue of patients with documented BEN, associated with the dominance of the A:T to T:A transversions in the p53 tumor suppressor gene mutational spectrum. (1) AA is a nephrotoxic and carcinogenic compound, which has been demonstrated to be genotoxic and mutagenic both in vitro and in vivo. Toxicity and carcinogenicity of the nephrotoxic compound aristolochic acid between rodents and humans suggest a species-dependent mechanism of action. AA had a comparable effect on the cell cycle in primary human and porcine cells and the rat NRK-52E cell line following 48 h exposure, also corroborated by the reduced 3H-thymidine incorporation in NRK-52E cells. In addition, DNA unwinding, suggestive of enhanced DNA damage, was observed in primary porcine cells. (2)

Metabolism

Aristolochic acids are absorbed after oral exposure. They are metabolized to aristolactams, which are further metabolized to a cyclic N-acylnitrenium ion, a re-active intermediateforming adducts with purine bases (adenine and guanine) in DNA (dA-AAI, dG-AAI, dA-AAII, and dG-AAII). A number of cytosolic and microsomal enzymes (CYP1A1, CYP1A2, NADPH:CYP reductase, prostaglandin H synthase, DT-diaphorase, xanthine oxidase, cyclooxygenase, and NAD(P)H:quinone oxidore-ductase) are capable of bioactivating aristolochic acids to the reactive form.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Aristolochic acid, defined as an extract of Aristolochia species comprising a mixture of aristolochic acid I and aristolochic acid II, is classified by IARC as carcinogenic to humans (Group 1). (3)

Uses/Sources

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links