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아리스토로크산

Aristolochic Acid

HCID 2236
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
10190-99-5
표준 SMILES
COc1cccc2c1cc([N+](=O)[O-])c1c(C(=O)O)cc3c(c12)OCO3
InChIKey
BBFQZRXNYIEMAW-UHFFFAOYSA-N
분자식
C17H11NO7
평균 분자량
341.27 g/mol
단동위원소 질량
341.05355169

개요

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.

이름 및 식별자

우선 이름
Aristolochic Acid
IUPAC
8-methoxy-6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid
현지명
아리스토로크산
영어명
Aristolochic acid
분자식
C17H11NO7
분자량
341.27

이름 및 동의어

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
이름 더 보기
아리스토로크산Aristolochic 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

데이터베이스 식별자

CAS
10190-99-5、313-67-7
PubChem CID
2236

물성

구조 계산 물성

XLogP
3.6
극성 표면적
111 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
7
회전 가능 결합 수
2
무거운 원자 수
25
형식 전하
0
복잡도
550

실험 및 물리화학적 성질

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]

물리화학적 성질

녹는점
260 °C · 260 °C
끓는 점
476.92 °C · 476.92°C (rough estimate)
밀도
1.3162 · 1.3162 (rough estimate)
굴절률
1.45 · 1.4500 (estimate)
저장 조건
2 · 2-8°C
용해도
DMSO: 용해될 수 있다
물리적 상태
가루
산도 계수 (pKa)
2.99 · 2.99±0.20(Predicted)
색상
노란색
주요 응용
의약품(소분자)
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

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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]

유해성 정보

Regulatory InformationHazard Traits - Carcinogenicity
Hazard Classes and Categories · 2건

Acute Tox. 3 (100%)

Acute Tox. 3 (100%)

독성 정보

Exposure RoutesOral
Toxicity Summary · 1건

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)

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

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 · 2건

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.

용도 및 제조

Uses · 1건

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.

응용 분야 · 4건

개요Aristolochic 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.

역사At 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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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
DTXSID
DTXSID0040969
ChEMBL
CHEMBL93353
ChEBI
CHEBI:2825
UNII
94218WFP5T
EC Number
206-238-3
Nikkaji
J20.596F

화학적 성질

Shiny brown leaflets or a yellow or white powder.

Carcinogen Classification · 6건

Aristolochic acid

Group 1: Carcinogenic to humans

Volume 82: (2002) Some Traditional Herbal Medicines, Some Mycotoxins, Naphthalene and Styrene

2012

2008

NB Overall evaluation upgraded to Group 1 based on mechanistic and other relevant data

안전 데이터

wgk
3
rtecs
CF3325000
ridadr
UN 1544 6.1/PG 3
독성
LD50 in male, female mice, male, female rats (mg/kg): 38.4, 70.1, 82.5, 74.0 i.v.; 55.9, 106.1, 203.4, 183.9 orally (Mengs)
HS 번호
29329990
risk_code
25-68-36/37/38-23/24/25-45
hazard_code
T
safety_code
7-35-45-36/37/39-26-53
포장분류
III
위험 등급
6.1(b)
Hazard Classifications
Acute Tox. 3 OralCarc. 1AMuta. 1B
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
중점관리물질 필터링
별표2-51

용도Aristolochic acids occur in Aristolochiaceae and in butterflies feeding on these plants. One of a group of fourteen known, substituted 1-phenanthrenecarboxylic acids

일반 설명This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

공급사100 곳

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추가 설명 · 1건

정의ChEBI: 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 b th carcinogenic and nephrotoxic.