Orientin

HCID 5281675CAS 28608-75-5
部分構造検索類似構造を探す

基本情報

標準SMILES
O=c1cc(-c2ccc(O)c(O)c2)oc2c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)cc(O)c12
InChIKey
PLAPMLGJVGLZOV-VPRICQMDSA-N
分子式
C21H20O11
平均分子量
448.4 g/mol
単同位体質量
448.10056146

概要

Orientin is a C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8. It has a role as an antioxidant and a metabolite. It is a C-glycosyl compound, a 3'-hydroxyflavonoid and a tetrahydroxyflavone. It is functionally related to a luteolin.

名称と識別子

優先名称
Orientin
IUPAC
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
英語名
ORIENTIN
分子式
C21H20O11
分子量
448.38

名称と別名

Orientin28608-75-5LutexinLuteolin 8-C-glucosideLuteolin-8-glucosideLuteolin-8-C-glucosideOrientine4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-8-beta-D-glucosylluteolinIAX93XCW6CLuteolin 8-C-beta-D-glucopyranosideJ17.734B
名称をさらに表示
PolygoninLuteolin 8-C-β-D-glucopyranosideAids026706Aids-026706ORIENTIN(P)ORIENTIN,NA
2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-oneMASSBANK PR020063CHEBI:7781DTXSID60182790C101142-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one2-(3,4-dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-4H-chromen-4-one2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)chromen-4-one

データベース識別子

CAS
28608-75-5
PubChem CID
5281675
DTXSID
DTXSID60182790
ChEMBL
CHEMBL520866
ChEBI
CHEBI:7781
UNII
IAX93XCW6C
EC Number
608-227-2
Nikkaji
J17.734B

物性

構造計算による物性

XLogP
-0.2
極性表面積
197 Ų
水素結合供与体数
8
水素結合受容体数
11
回転可能結合数
3
重原子数
32

実験および物理化学的性質

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Endocrine DisruptorsPotential endocrine disrupting compound

物理化学的性質

Melting point
260 · 260-285°C
Boiling point
816.1 · 816.1±65.0 °C(Predicted)
Density
1.759 · 1.759±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C(protect from light)
solubility
1 M · 1 M NaOH: soluble1mg/mL, clear, yellow-orange
pka
6.24 · 6.24±0.40(Predicted)

安全と法規制

GHS分類

GHS ClassificationNot Classified

危険有害性情報

Hazard Classes and CategoriesNot Classified

安全データ

wgk
3
rtecs
DJ3009300
hs_code
29389090
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
24/25

化学と産業

応用分野 · 2 件

DescriptionOrientin is a flavone glycoside originally isolated from P. orientale that has diverse biological activities, including antioxidant, antibacterial, and anti-inflammatory properties. Orientin scavenges 2,2-diphenyl-1-picryl-hydrazyl (DPPH; ) radicals with an IC50 value of 316.21 μg/ml. It also decreases the cytopathic effects of parainfluenza type 3 virus with an IC50 value of 11.7 μg/ml and a cytotoxic concentration (CC50) value of 375 μg/ml in Hep-2 cells. Orientin (5-40 μM) inhibits LPS-induced barrier disruption, decreases the expression of toll-like receptor 4 (TLR4), phosphorylated p38, and NF-κB, and decreases TNF-α production and IL-6 secretion in a dose-dependent manner in human umbilical vein endothelial cells (HUVECs). It also prolongs survival in a mouse model of LPS-induced lethal endotoxemia when administered at a dose of 36 μg/animal 12 hours after LPS administration.

UsesOrientin is a flavone, a chemical flavonoid compound. Orientin have been investigated for its anti-oxidant, antihypertensive and antihyperlipidemic effects.

サプライヤー19 社

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都普睿法药物研发有限公司82633860 18982077548 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]

補足説明

DefinitionChEBI: A C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8.

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