基本情報
- CAS
10190-99-5- 標準SMILES
COc1cccc2c1cc([N+](=O)[O-])c1c(C(=O)O)cc3c(c12)OCO3- InChIKey
BBFQZRXNYIEMAW-UHFFFAOYSA-N- 分子式
- C17H11NO7
- 平均分子量
- 341.27 g/mol
- 単同位体質量
- 341.05355169
概要
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.
名称と識別子
- 優先名称
- Aristolochic Acid
- IUPAC
- 8-methoxy-6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid
- 現地名
- 3,4-メチレンジオキシ-8-メトキシ-10-ニトロフェナントレン-1-カルボン酸
- 英語名
- Aristolochic acid
- 分子式
- C17H11NO7
- 分子量
- 341.27
名称と別名
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
名称をさらに表示
6-ニトロ-8-メトキシフェナントロ[3,4-d]-1,3-ジオキソール-5-カルボン酸8-メトキシ-6-ニトロフェナントロ[3,4-d]-1,3-ジオキソール-5-カルボン酸アリストロク酸I8-メトキシ-10-ニトロ-3,4-(エポキシメタノキシ)フェナントレン-1-カルボン酸アリストロキン酸3,4-メチレンジオキシ-8-メトキシ-10-ニトロフェナントレン-1-カルボン酸アリストロキア酸アリストロク酸Aアリストロキン酸Iアリストロク酸アストロキン酸アリストロキン酸Aアリストロチク酸A8-メトキシ-6-ニトロ-2H-フェナントロ[3,4-d][1,3]ジオキソール-5-カルボン酸Aristolochic acid ⅠAristolochicAristolochic acid ⅢIsoaristolochic acidAristolochic acid I,TR 17363,4-methylenedioxy-8-methoxy-10-nitro-1-phenanthrenecarboxylicacid
物性
構造計算による物性
- XLogP
- 3.6
- 極性表面積
- 111 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 7
- 回転可能結合数
- 2
- 重原子数
- 25
- 形式電荷
- 0
- 複雑度
- 550
実験および物理化学的性質
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]
物理化学的性質
- 融点
- 260 °C · 260 °C
- 沸点
- 476.92 °C · 476.92°C (rough estimate)
- 比重(密度)
- 1.3162 · 1.3162 (rough estimate)
- 屈折率
- 1.45 · 1.4500 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- DMSO：可溶
- 外見
- 粉
- 酸解離定数(Pka)
- 2.99 · 2.99±0.20(Predicted)
- 色
- 黄色
- 主な用途
- 医薬品（低分子化合物）
- 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)
- InChIKey
- LIDQMWRBMLSXLL-UHFFFAOYSA-N
- SMILES
- O1C2=C3C(=C(C(O)=O)C=C2OC1)C([N+]([O-])=O)=CC1C3=CC=CC=1OC
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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]
危険有害性情報
Regulatory InformationHazard Traits - Carcinogenicity
Hazard Classes and Categories
Acute Tox. 3 (100%)
Acute Tox. 3 (100%)
毒性情報
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)
化学と産業
薬理情報
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.
用途と製造
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.
応用分野
説明Aristolochic 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.
来歴At a clinic in Brussels, Belgium, a group of women who had all taken the same weight loss supplement, Aristolochia fangchi, which contained aristolochic acid, was first diagnosed with aristolochic acid poisoning. Balkan endemic nephropathy (BEN) was later found to be also the result of aristolochic acid (AA) consumption. Balkan endemic nephropathy is likely caused by low-level AA exposure, possibly from the contamination of wheat flour seeds by Aristolochia clematitis. BEN falls under the umbrella of what is now known as aristolochic acid nephropathy, the prevalent symptom of AA poisoning .
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