基本情報
- 標準SMILES
COc1ccc([C@@H]2CC(=O)c3c(O)cc(O)cc3O2)cc1O- InChIKey
AIONOLUJZLIMTK-AWEZNQCLSA-N- 分子式
- C16H14O6
- 平均分子量
- 302.28 g/mol
- 単同位体質量
- 302.07903817
概要
Hesperetin is a trihydroxyflavanone having the three hydroxy gropus located at the 3'-, 5- and 7-positions and an additional methoxy substituent at the 4'-position. It has a role as an antioxidant, an antineoplastic agent and a plant metabolite. It is a member of 4'-methoxyflavanones, a monomethoxyflavanone, a trihydroxyflavanone and a member of 3'-hydroxyflavanones. It is a conjugate acid of a hesperetin(1-).
名称と識別子
- 優先名称
- Hesperetin
- IUPAC
- (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
- 英語名
- HESPERETIN
- 分子式
- C16H14O6
- 分子量
- 302.28
名称と別名
名称をさらに表示
データベース識別子
- CAS
41001-90-5、520-33-2- PubChem CID
- 72281
- DTXSID
DTXSID4022319- ChEMBL
CHEMBL399121- ChEBI
CHEBI:28230- UNII
- Q9Q3D557F1
- EC Number
- 208-290-2、805-255-9
- Nikkaji
- J9.235E
物性
構造計算による物性
- XLogP
- 2.4
- 極性表面積
- 96.2 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 6
- 回転可能結合数
- 2
- 重原子数
- 22
- 形式電荷
- 0
- 複雑度
- 413
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Metabolite of Hesperidin
LogP
2.60
2.6
Collision Cross Section
175.82 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
184.45 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
169.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
177.9 Ų [M-H]-
物理化学的性質
- 貯蔵温度
- 2 · 2-8°C
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 97.9% (92 of 94) of all reports.
Not Classified
Aggregated GHS information provided per 94 reports by companies from 3 notifications to the ECHA C&L Inventory.
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory Information
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories
Not Classified
Not Classified
安全データ
- wgk
- 3
化学と産業
薬理情報
Pharmacodynamics
Hesperetin is a cholesterol lowering flavanoid found in a number of citrus juices. It appears to reduce cholesteryl ester mass and inhibit apoB secretion by up to 80%. Hesperetin may have antioxidant, anti-inflammatory, anti-allergic, hypolipidemic, vasoprotective and anticarcinogenic actions.
Mechanism of Action
Hesperetin reduces or inhibits the activity of acyl-coenzyme A:cholesterol acyltransferase genes (ACAT<sub>1</sub> and ACAT<sub>2</sub>) and it reduces microsomal triglyceride transfer protein (MTP) activity. Hesperetin also seems to upregulate the LDL receptor. This leads to the reduced assembly and secretion of apoB-containing lipoproteins and enhanced reuptake of those lipoproteins, thereby lowering cholesterol levels.
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