Basic information
- CAS
10190-99-5- Standard SMILES
COc1cccc2c1cc([N+](=O)[O-])c1c(C(=O)O)cc3c(c12)OCO3- InChIKey
BBFQZRXNYIEMAW-UHFFFAOYSA-N- Molecular formula
- C17H11NO7
- Average molar mass
- 341.27 g/mol
- Monoisotopic mass
- 341.05355169
Overview
Aristolochic acid A is an aristolochic 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 metabolite, a mutagen, a carcinogenic agent and a nephrotoxin. It is a member of aristolochic acids, a monocarboxylic acid, an aromatic ether, a C-nitro compound, an organic heterotetracyclic compound and a cyclic acetal.
Names & identifiers
- Preferred name
- Aristolochic Acid
- IUPAC
- 8-methoxy-6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid
- English name
- Aristolochic acid
- Molecular formula
- C17H11NO7
- Molecular weight
- 341.27
Names & synonyms
Aristolochic acidAristolochic acid A313-67-7Aristolochic acid IAristolochinTardolytARISTOLOCHINEAristolochic acid-ITR 17368-Methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acidNSC-504138-Methoxy-3,4-methylenedioxy-10-nitrophenanthrene-1-carboxylic acid
Show more names
Aristolochic acid ⅠAristolochicAristolochic acid ⅢIsoaristolochic acidAristolochic acid I,TR 17363,4-methylenedioxy-8-methoxy-10-nitro-1-phenanthrenecarboxylicacid
3,4-Methylenedioxy-8-methoxy-10-nitro-1-phenanthrenecarboxylic acid8-Methoxy-6-nitrophenanthol (3,4-d) 1,3-dioxole-5-carboxylic acidCHEBI:2825DTXSID004096994218WFP5TNSC-11926TR-17368-methoxy-6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid
Database identifiers
- CAS
10190-99-5、313-67-7- PubChem CID
- 2236
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 111 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 550
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section185.6 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3020099]
Physicochemical properties
- Melting point
- 260 °C · 260 °C
- Boiling point
- 476.92 °C · 476.92°C (rough estimate)
- Density
- 1.3162 · 1.3162 (rough estimate)
- refractive index
- 1.45 · 1.4500 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO: soluble
- form
- powder
- pka
- 2.99 · 2.99±0.20(Predicted)
- color
- yellow
- Major Application
- pharmaceutical (small molecule)
- 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)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 6 notifications to the ECHA C&L Inventory.
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
Hazard information
Regulatory InformationHazard Traits - Carcinogenicity
Hazard Classes and Categories
Acute Tox. 3 (100%)
Acute Tox. 3 (100%)
Toxicology
Exposure RoutesOral
Toxicity Summary
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. (A15444) 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. (A15445)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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.
MeSH Pharmacological Classification
Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.
Uses & manufacturing
Uses
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.
Applications
DescriptionAristolochic acid first appeared in Chinese medicine in the fifth century AD, while it was used to treat kidney and urinary diseases, as well as gout, snakebites, and a variety of other ailments. In many of these cases, aristolochic acid was just one of the main components of the salves. In the first century, aristolochic acid was first described as a composition of ingested medicine to treat symptoms such as asthma, hiccups, pains, and spasms.
Related reactions
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Compound notes
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