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Nevadensin

HCID 178785948
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Grundinformationen

CAS
152743-19-6
Standard-SMILES
COc1ccc(-c2cc(=O)c3c(O)c(OC)c(O)c(OC)c3o2)cc1
InChIKey
KRFBMPVGAYGGJE-UHFFFAOYSA-N
Summenformel
C18H16O7
Durchschnittliche Molmasse
344,3 g/mol

Überblick

Nevadensin is a trimethoxyflavone that is flavone substituted by methoxy groups at positions 6, 8 and 4' and hydroxy groups at positions 5 and 7 respectively. It has a role as a plant metabolite. It is a trimethoxyflavone and a dihydroxyflavone. It is functionally related to a flavone. It is a conjugate acid of a nevadensin-7-olate.

Namen und Bezeichner

Bevorzugter Name
Nevadensin
IUPAC
5,7-dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
Englischer Name
LYSIONOTIN
Summenformel
C18H16O7
Molmasse
344.317

Namen und Synonyme

Nevadensin10176-66-65,7-dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)chromen-4-oneDTXSID40144174CHEBI:75455,7-Dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-oneRefChem:165603DTXCID5066665Lysionotin152743-19-6nebadensinLysionatin
Weitere Namen anzeigen
Lysionotin ,98%shidiaolanjiasuLYSIONOTIN USP/EP/BPLysionotin (Standard)Lysionotin 152743-19-6Lysionotin, 10 mM in DMSO
5,7-Dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-oneMFCD086899474H-1-Benzopyran-4-one, 5,7-dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-5,7-dihydroxy-6,8,4'-trimethoxyflavoneNevadensin ANevadensin (Standard)CHEMBL312073MEGxp0_001862

Datenbank-Bezeichner

CAS
152743-19-6
ChEMBL
CHEMBL312073
ChEBI
CHEBI:7545
Nikkaji
J94.491B

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
2,9
Polarare Oberfläche (TPSA)
94,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
4
Schwere Atome
25
Formalladung
0
Komplexität
512

Experimentelle und physikochemische Eigenschaften

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Collision Cross Section131 Ų [M-H]-

Chemie und Industrie

Anwendungen · 2 Einträge

BeschreibungChinese stone Chlorophytum is the whole herb of Lysionotus pauciflorus Maxim, which belongs to Gesneriaceae. Stone Chlorophytum is a small evergreen shrub, which is born in wet places of rock slope and clings to the stone or a tree. Cutting stone Chlorophytum in summer and autumn season when leafiness, removing impu rities, and drying. Stone Chlorophytum is more in Jiangsu, Zhejiang, Anhui, Jiangxi, Hunan, Hubei, Shaanxi, Sichuan, Yunnan, Guizhou, and Guangxi.Stone Chlorophytum has a long medical history in Yunnan, Guizhou, and south of Qinling region. The function was described in various previous dynasty medicine classics. Stone Chlorophytum tastes bitter, is flat, and goes into the lung, liver, and kidney meridians. It has been recorded in herbal formula that stone Chlorophytum could eliminate sputum and poison, promote digestion, nourish blood, and cure rheumatism, emphysema, dizziness, and various kinds of deficiency. In the classifi cation of herbs, it was recorded that stone Chlorophytum could cure hematemesis, blood vomiting, pain of waist and knee, and contusions. It has been described incommon folk medicinal herbs that stone Chlorophytum could clear the lung to relieve cough, cool blood, and hemostasis .

HistoryStone Chlorophytum is the folk antituberculous herb, the fat-soluble component separated from which is lysionotin. China’s scientists for the first time found that lysionotin is the effective component of the antituberculosis in stone Chlorophytum. Xu Yin et al., who worked in Shanghai Institute of Materia Medica, Chinese Academy of Sciences, found that lysionotin is 5,7-dihydroxy 4′,6′,8-trimethoxy flavonoids by structure identification, which is the known compound nevadensin Farkas et al. used a 14-step synthesis to demonstrate the structure of nevadensin with complex reaction steps. The synthesis route was simpler, which was designed by Tang Cheng-fang in Shanghai Institute of Materia Medica, Chinese Academy of Sciences, and the total yield was ten times higher . oluble, clinical use of injection caused pain to the patients. In order to overcome the above shortcomings, methylamine glucoside salt of nevadensin was synthesized for intramuscular injection. The effect is significant without causing pain. In order to explore its structure-activity relationship, seven chemical analogues were designed and synthesized with good activity in antibacterial test of Mycobacterium tuberculo sis, which include 6,8-dichloro-4′-methoxyflavone, 6,7-dimethyl-4′-methoxyflavone, 6,7-dichloro-4′-methoxyflavone, dimethoxy-3′, 4′-dimethoxyflavone, 6,7-dichloro-3′, 4′-dimethoxyflavone, 6-chloro-4′-methoxyflavone, and 4-dichloro 6-(4-methoxybenzoyloxy) acetophenone (Fig. 3)

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