Aristolochic acid (CED0004380)

Record Information

Version

1.0

Creation Date

2014-08-29 05:17:15 UTC

Update Date

2026-08-19 18:18:27 UTC

SynCED ID

CED0004380

Secondary Accession Numbers

CHEM003073
T3D4113

Identification

Common Name

Aristolochic acid

Class

Small Molecule

Description

Aristolochic acid is an exogenous solid with the formula C17H11NO7 and an average molecular weight of 341.27 g/mol. Aristolochic acid belongs to the aristolochic acids and derivatives, a subclass of phenanthrenes and derivatives within the organic compounds. Biologically, it functions as a toxin, nephrotoxin, mutagen, carcinogenic agent, and metabolite. It has one recorded protein target, Cyclin-dependent kinase 2 (CDK2). The compound is found in 22 recorded sources across several sectors. In electrical and electronic equipment, it is present in batteries, capacitors, cell phones, printed circuit boards, wires, and cables, among three other items. Within household cleaning and consumer products, it is found in soap detergents, cigar cigarettes, non-electric simulated smoking devices, other smoking requisites, and tobacco smoke filters. Its presence in food, food processing, and cookware includes food packaging, food preservation, and the preparation of vinegar. Additionally, it is found in lubricants within the energy, oil, and gas sector, medical devices in healthcare, pharmaceuticals, and veterinary products, and synthetic textiles, carpets, and rugs in textiles, leather, and furnishings. Exposure to aristolochic acid occurs through oral, inhalation, and touch routes.

Contaminant Type

Ester
Ether
Natural Compound
Organic Compound
PFAS
Phytotoxin
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

Applications

Not Available

Biological Roles

mutagen (PMC13415939 )?A chemical substance that alters the genetic material of an organism, and increases the frequency of mutations above the naturally-occuring rate
carcinogenic agent (PMC8902436 , PMC5752374 )?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.
metabolite ?A chemical produced during metabolism process, as an intermediate or end-product
antiviral agent (PMC7092833 )?
nephrotoxin (PMC5752374 , PMC5056140 )?A chemical substance that interferes with the normal functioning of the kidneys
toxin (PMC3870154 , PMC4750486 )?A chemical substance naturally produced by an organism and poisonous to other organisms
nephrotoxic agent (PMC5716161 )?A role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals.

Chemical Roles

Not Available

Organoleptic Effects

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	Yes	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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-01oy-3097000000-da70a568598192c4149d	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0009000000-192503bd944b4098f295	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0019000000-36268a06fdb878508480	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-022d-0059000000-e1c393e1f4dcf97ab02c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0009000000-ec56c61ed56ce4fdd6d5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0009000000-0f6cf8b2fee975ef3311	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0016-2093000000-237334dcb4e6c37619ae	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
3729.0 Log mg/kg [2100:6600]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

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)

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)

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
arthritis	Not Available	Not Available	A disorder characterized by inflammation involving a joint. (NCI CTCAE)	PMC4519959
cancer	Associated With?	Not Available	Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. Possible signs and symptoms include a lump, abnormal bleeding, prolonged cough, unexplained weight loss, and a change in bowel movements. There are over 100 types of cancers affect humans. The risk of developing certain cancers can be reduced by not smoking, maintaining a healthy weight, not drinking too much alcohol, eating plenty of vegetables, fruits and whole grains, vaccination against certain infectious diseases, not eating too much processed and red meat and avoiding too much sunlight exposure. Cancer is often treated with some combination of radiation therapy, surgery, chemotherapy and targeted therapy. The majority of cancers, some 90–95% of cases, are due to genetic mutations from environmental and lifestyle factors. The remaining 5–10% are due to inherited genetics.	PMC12804237
kidney disease	Associated With?	Not Available	A urinary system disease that is located in the kidney. (DO)	PMC9469194 , PMC12804237
infertility	Associated With?	Not Available	A disorder characterized by the inability to reproduce by natural means.	PMC10499588
stroke	Not Available	Not Available	Not Available	PMC13415939
rheumatoid arthritis	Not Available	Not Available	An arthritis that is an autoimmune disease which attacks healthy cells and tissue located in joint. (DO)	PMC13415939
chronic kidney disease	Associated With?	Not Available	A disorder characterized by gradual and usually permanent damage/loss of kidney function resulting in renal failure. (NCI CTCAE)	PMC4750486
gout	Not Available	Not Available	An arthritis that has material basis in uric acid crystal deposits located in joint. (DO)	PMC4519959
pneumonia	Not Available	Not Available	A lung disease that involves lung parenchyma or alveolar inflammation and abnormal alveolar filling with fluid (consolidation and exudation). It results from a variety of causes including infection with bacteria, viruses, fungi or parasites, and chemical or physical injury to the lungs. It is accompanied by fever, chills, cough, and difficulty in breathing. (DO)	PMC13415939
kidney cancer	Associated With?	Not Available	A urinary system cancer that is located in the kidney. (DO)	PMC8902436 , PMC10939812
Neoplasms	Has Therapeutic Effect On	Not Available	Not Available	PMC12478143
Rheumatic Diseases	Not Available	Not Available	Not Available	PMC4519959
Balkan nephropathy	Associated With?	Not Available	Not Available	PMC6476903 , PMC12561251
Snake Bites	Not Available	Not Available	Not Available	PMC7092833

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000007	Pesticides?Pesticides are synthetic chemicals designed to prevent, destroy, or control pests that threaten crops and agricultural productivity.	Agriculture & land management	Not Available
CEDs000010	Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.	Agriculture & land management	PubChem
CEDs000013	Soil?Soil serves as a critical medium for plant growth and sustains various ecological functions; however, it can become a reservoir for synthetic chemical contamination.	Agriculture & land management	PMC6468885
CEDs000070	Stormwater runoff?Stormwater runoff refers to the flow of rainwater or melted snow that does not soak into the ground and instead collects pollutants as it travels over impervious surfaces such as roads and parking lots.	Automotive & urban infrastructure	PubChem
CEDs000120	Wires and cables?Wires and cables are integral components in the transmission of electrical power and signals.	Electrical & Electronic Equipment	Not Available
CEDs000121	Printed circuit boards?Printed circuit boards (PCBs) are essential components in the manufacturing of electronic devices, serving as the backbone for electrical connections and circuit pathways.	Electrical & Electronic Equipment	Not Available
CEDs000125	Batteries?Batteries are devices that store and release electrical energy through electrochemical reactions.	Electrical & Electronic Equipment	Not Available
CEDs000130	Semiconductors?Semiconductors are materials that possess electrical conductivity between that of conductors and insulators, making them essential for various electronic applications, including transistors, diodes, and integrated circuits.	Electrical & Electronic Equipment	Not Available
CEDs000138	Lubricants?Lubricants are synthetic or petroleum-derived substances used to reduce friction between surfaces in machinery and equipment, enhancing operational efficiency and longevity.	Energy, oil & gas	Not Available
CEDs000147	Food packaging?Food packaging often utilizes synthetic chemicals, such as plastics and coatings, to enhance durability, moisture resistance, and shelf life.	Food, food processing & cookware	Not Available
CEDs000174	Lubricants?Lubricants are synthetic or petroleum-based substances used to reduce friction and wear between moving parts in machinery and equipment.	Industrial manufacturing & chemical processing	Not Available
CEDs000234	Medical devices?Medical devices often incorporate synthetic chemicals in their manufacturing processes, which can contribute to contamination in healthcare settings.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000451	Carpets and Rugs?Carpets and rugs are commonly manufactured using synthetic fibers such as nylon, polyester, and polypropylene, which can be derived from petrochemical sources.	Textiles, leather & furnishings	Not Available
CEDs000454	Synthetic textiles?Synthetic textiles are materials derived from man-made fibers, such as polyester, nylon, and acrylic, which are produced through chemical processes involving petrochemicals.	Textiles, leather & furnishings	Not Available
CEDs000490		Personal care & cosmetics	Not Available
CEDs000492	Cell phones?Cell phones contain a variety of synthetic chemicals and materials, including plastics, metals, and glass, which can contribute to environmental contamination.	Electrical & Electronic Equipment	Not Available
CEDs000493	Capacitors?Capacitors are electronic components that store and release electrical energy, often using dielectric materials that can include synthetic chemicals.	Electrical & Electronic Equipment	Not Available
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000548	Preparation Of Vinegar?Vinegar is produced through the fermentation of ethanol by acetic acid bacteria, resulting in a solution that typically contains 4-8% acetic acid.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000578	Making Cigars?The process of making cigars involves several steps, including the cultivation of tobacco, fermentation, and the application of various additives to enhance flavor and preservation.	Industrial manufacturing & chemical processing	PubChem
CEDs000579	Manufacture Of Iron Or Steel?The manufacture of iron or steel involves various processes, including smelting, refining, and alloying, which can result in the release of synthetic chemicals and contaminants.	Industrial manufacturing & chemical processing	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000600	Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.	Agriculture & land management	PubChem
CEDs000602	Molluscicides?Molluscicides are synthetic chemicals specifically designed to control and eliminate mollusks, such as snails and slugs, which can be detrimental to crops and agricultural productivity.	Agriculture & land management	PubChem
CEDs000603	Nematocides?Nematocides are synthetic chemicals specifically designed to control nematodes, which are microscopic roundworms that can cause significant damage to crops and plants.	Agriculture & land management	PubChem
CEDs000606	Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.	Agriculture & land management	PubChem
CEDs000609	Aftershave?Aftershave is a grooming product typically used to soothe and protect the skin following shaving.	Personal care & cosmetics	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000617	Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000662	Yarns Or Threads?Yarns or threads used in textiles can be a source of synthetic chemical contamination due to the production processes and treatments they undergo.	Textiles, leather & furnishings	PubChem
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	PubChem
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000734	Coating Compositions?Coating compositions, which include paints, sealants, and varnishes, are formulated with a variety of synthetic chemicals such as solvents, resins, pigments, and additives.	Building & Construction	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem
CEDs00805	Soil Organic Matter	Agriculture & land management	PMC6468885
CEDs01144	Food	Food, food processing & cookware	PMC6468885
CEDs01183	Wheat	Food, food processing & cookware	PMC6476903
CEDs01188	Flour	Food, food processing & cookware	PMC6476903 , PMC6476903
CEDs01228	Tomato Fruits	Food, food processing & cookware	PMC6468885
CEDs01542	Food Grains	Food, food processing & cookware	PMC6468885
CEDs01558	Wheat Grain	Food, food processing & cookware	PMC6468885 , PMC6468885

Pathways

9 pathwaysPathway Source: PathBank

Glutathione Metabolism

Dna replication

Arachidonic Acid Metabolism

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820	Humans	Predicted (SEA)	Prediction Confidence Score 0.28 Applicability Domain 0.306 Statistical Significance 0.0362 Supporting Reference Compounds 343 E-value 281.658
Click to view 3D structure	Secreted chorismate mutase	P9WIB9	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	Prediction Confidence Score 0.272 Applicability Domain 0.272 Low confidence Statistical Significance 0.0014 Supporting Reference Compounds 1 E-value 10.6653
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	Prediction Confidence Score 0.271 Applicability Domain 0.333 Statistical Significance 0.0731 Supporting Reference Compounds 372 E-value 568.844
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	Prediction Confidence Score 0.271 Applicability Domain 0.333 Statistical Significance 0.0647 Supporting Reference Compounds 332 E-value 503.607
Click to view 3D structure	Protoporphyrinogen oxidase, mitochondrial	O24164	Nicotiana tabacum	Predicted (SEA)	Prediction Confidence Score 0.27 Applicability Domain 0.27 Low confidence Statistical Significance 0.0015 Supporting Reference Compounds 1 E-value 11.6774
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.267 Applicability Domain 0.297 Low confidence Statistical Significance 0.063 Supporting Reference Compounds 297 E-value 490.839
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	Prediction Confidence Score 0.266 Applicability Domain 0.333 Statistical Significance 0.0386 Supporting Reference Compounds 172 E-value 300.342
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	Prediction Confidence Score 0.266 Applicability Domain 0.333 Statistical Significance 0.0891 Supporting Reference Compounds 407 E-value 693.87
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.265 Applicability Domain 0.303 Statistical Significance 0.2039 Supporting Reference Compounds 1103 E-value 1587.03
Click to view 3D structure	Aldo-keto reductase family 1 member C3	P42330	Humans	Predicted (SEA)	Prediction Confidence Score 0.263 Applicability Domain 0.314 Statistical Significance 0.0221 Supporting Reference Compounds 57 E-value 172.436
Click to view 3D structure	Aldo-keto reductase family 1 member C2	P52895	Humans	Predicted (SEA)	Prediction Confidence Score 0.263 Applicability Domain 0.314 Statistical Significance 0.0179 Supporting Reference Compounds 40 E-value 139.739
Click to view 3D structure	Heat shock factor protein 1	P38532	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.261 Applicability Domain 0.306 Statistical Significance 0.0447 Supporting Reference Compounds 166 E-value 348.142
Click to view 3D structure	Tyrosine-protein kinase Lck	P06239	Humans	Predicted (SEA)	Prediction Confidence Score 0.26 Applicability Domain 0.28 Low confidence Statistical Significance 0.3168 Supporting Reference Compounds 1130 E-value 2465.95
Click to view 3D structure	ATP-dependent molecular chaperone HSP82	C4YTQ8	Candida albicans (strain WO-1) (Yeast)	Predicted (SEA)	Prediction Confidence Score 0.259 Applicability Domain 0.284 Low confidence Statistical Significance 0.0445 Supporting Reference Compounds 205 E-value 346.585
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	Prediction Confidence Score 0.259 Applicability Domain 0.333 Statistical Significance 0.0473 Supporting Reference Compounds 165 E-value 368.538
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	Prediction Confidence Score 0.259 Applicability Domain 0.289 Low confidence Statistical Significance 0.3365 Supporting Reference Compounds 1301 E-value 2620.02
Click to view 3D structure	Sentrin-specific protease 8	Q96LD8	Humans	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.314 Statistical Significance 0.0192 Supporting Reference Compounds 104 E-value 149.704
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.267 Low confidence Statistical Significance 0.118 Supporting Reference Compounds 425 E-value 918.621
Click to view 3D structure	Tyrosine-protein kinase Fyn	P06241	Humans	Predicted (SEA)	Prediction Confidence Score 0.253 Applicability Domain 0.28 Low confidence Statistical Significance 0.2878 Supporting Reference Compounds 707 E-value 2240.5
Click to view 3D structure	Metabotropic glutamate receptor 4	Q68EF4	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.253 Applicability Domain 0.253 Low confidence Statistical Significance 4.90e-04 Supporting Reference Compounds 1 E-value 3.81461
Click to view 3D structure	Aminopeptidase N	O96935	Plasmodium falciparum FcB1/Columbia	Predicted (SEA)	Prediction Confidence Score 0.253 Applicability Domain 0.279 Low confidence Statistical Significance 0.012 Supporting Reference Compounds 23 E-value 93.1077
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.252 Applicability Domain 0.286 Low confidence Statistical Significance 0.0766 Supporting Reference Compounds 208 E-value 596.014
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.252 Applicability Domain 0.286 Low confidence Statistical Significance 0.2581 Supporting Reference Compounds 823 E-value 2009.6
Click to view 3D structure	Fatty acid synthase	P49327	Humans	Predicted (SEA)	Prediction Confidence Score 0.251 Applicability Domain 0.273 Low confidence Statistical Significance 0.0381 Supporting Reference Compounds 117 E-value 296.294
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.251 Applicability Domain 0.286 Low confidence Statistical Significance 0.5372 Supporting Reference Compounds 1498 E-value 4182.06
Click to view 3D structure	Organic anion transporter 3	Q8TCC7	Humans	Known	Not Available
Click to view 3D structure	Cyclin-dependent kinase 2	P24941	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001526

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Aristolochic_acid

Chemspider ID

2149

ChEBI ID

2825

PubChem Compound ID

Not Available

Kegg Compound ID

C08469

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

De Broe ME: Chinese herbs nephropathy and Balkan endemic nephropathy: toward a single entity, aristolochic acid nephropathy. Kidney Int. 2012 Mar;81(6):513-5. doi: 10.1038/ki.2011.428. [PubMed: 22373701]
Huljic S, Bruske EI, Pfitzenmaier N, O'Brien E, Dietrich DR: Species-specific toxicity of aristolochic acid (AA) in vitro. Toxicol In Vitro. 2008 Aug;22(5):1213-21. doi: 10.1016/j.tiv.2008.04.002. Epub 2008 Apr 10. [PubMed: 18499390]
International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. - http://monographs.iarc.fr/index.php
http://en.wikipedia.org/wiki/Aristolochic_acid - http://en.wikipedia.org/wiki/Aristolochic_acid

Aristolochic acid (CED0004380)

Structure for CHEM003073: Aristolochic acid

Structure