Plumbagin

HCID 10205CAS 481-42-5

기본 정보

표준 SMILES
CC1=CC(=O)c2c(O)cccc2C1=O
InChIKey
VCMMXZQDRFWYSE-UHFFFAOYSA-N
분자식
C11H8O3
평균 분자량
188.18 g/mol
단동위원소 질량
188.04734412

개요

Plumbagin is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively. It has a role as a metabolite, an antineoplastic agent, an anticoagulant and an immunological adjuvant. It is a hydroxy-1,4-naphthoquinone and a member of phenols.

이름 및 식별자

우선 이름
Plumbagin
IUPAC
5-hydroxy-2-methylnaphthalene-1,4-dione
영어명
PLUMBAGIN
분자식
C11H8O3
분자량
188.18

이름 및 동의어

Plumbagin481-42-55-hydroxy-2-methylnaphthalene-1,4-dionePlumbagine5-Hydroxy-2-methyl-1,4-naphthoquinone2-MethyljuglonePlumbaeinPlumbagone5-Hydroxy-2-methyl-1,4-naphthalenedione2-Methyl-5-hydroxy-1,4-naphthoquinone5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dioneNSC-236613
이름 더 보기
plumaginplumbapinPLUMBAGANNSC 236613NSC 688284
YAS4TBQ4OQNSC-688284PCUR-101CHEBI:8273RefChem:863847PCUR101PCUR 101Synthetic Plumbagin PCUR-101

데이터베이스 식별자

CAS
481-42-5
PubChem CID
10205
DTXSID
DTXSID8075413
ChEMBL
CHEMBL295316
ChEBI
CHEBI:8273
UNII
YAS4TBQ4OQ
EC Number
207-569-6
Nikkaji
J5.778I

물성

구조 계산 물성

XLogP
2.3
극성 표면적
54.4 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
0
무거운 원자 수
14

실험 및 물리화학적 성질

SpringerMaterials PropertiesChemical shift
Collision Cross Section · 2건

124.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

134.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
76 · 76-78 °C(lit.)
끓는 점
283.17 °C · 283.17°C (rough estimate)
밀도
1.354 · 1.354
굴절률
1.631 · 1.6310 (estimate)
저장 조건
-20 °C · -20°C
용해도
very faint turbidity in hot Methanol

화학적 성질

ORANGE CRYSTALLINE POWDER OR CRYSTALS

안전 및 규제

GHS 분류

GHS Classification · 4건

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P264+P265, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 69 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 3 (100%)

안전 데이터

wgk
3
rtecs
QL8500000
ridadr
UN 2923 8/PG 2
독성
LD50 i.p. in mice: ~0.015 g/kg (Debray)
HS 번호
29146990
risk_code
25-34-36/37/38

화학 및 산업

약리 정보

MeSH Pharmacological Classification · 6건

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.

Agents that prevent BLOOD CLOTTING.

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).

Chemical substances that prevent or reduce the probability of CONCEPTION.

응용 분야 · 3건

개요Plumbagin is a natural 1,4-naphthoquinone first isolated from plants of the genus Plumbago. It has diverse effects in cells and animals. Plumbagin causes the generation of reactive oxygen species and induces apoptosis in cancer cells. It activates signaling through Nrf2 and the antioxidant response element, inducing the expression of Nrf2 target genes, including NQO1 and heme oxygenase-1 in cultured neuronal cells. Plumbagin also inhibits NADPH oxidase 4 in a time- and dose-dependent manner. It can be protective against peroxide stress or deprivation of glucose or oxygen.

용도Plumbagin from Plumbago indica has been used: as a reactive oxygen species agent (ROS) to induce cytotoxicity in mouse embryonic fibroblastsas an oxidative stress inducer to generate superoxide anion in Saccharomyces cerevisiaeas a reference standard in thin layer chromatography and in spectrophotometric analysis for quantification of plumbagin in Plumbago auriculate samples

일반 설명Plumbagin is a bioactive naphthoquinone present majorly in Plumbago indica L. It is a quinoid and is also derived from the roots of Plumbago zeylanicaroots.

공급사50 곳

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]

추가 설명

정의ChEBI: A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.

관련 반응

1건

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