H2614161计算溶液所需的质量、体积或浓度。
| 活性类型 | 活性值-log(M) | 作用机制 | 期刊 | 参考文献(PubMed IDs) |
|---|
有货
为什么选择此级别
Moligand™,分析标准品 级 提供 ≥98% 纯度，适用于对基线干扰要求严格的色谱和分析工作流程。
储存与运输
2-8°C储存。低温运输 。请查阅批次 COA 获取详细规格。
质量文档
SDS、COA、产品数据表及规格说明书均可下载。可通过批号查询获取批次 COA。
文献证明
在色谱分析、有机合成和交叉偶联反应领域已被 68 篇同行评审文献引用。
概述
Baicalein is a cell-permeable flavone, originally isolated from the roots of Scutellaria baicalensis, that inhibits cellular Ca2+ uptake, calcium mobilization, and adjuvant-induced arthritis. Baicalein has been shown to inhibit platelet 5-LO (5-lipoxygenase) (IC50=9.5 mM) and 12-LO (12-lipoxygenases) (IC50=0.12 mM) and reverse transcriptase. Baicalein reduces leukotriene biosynthesis and inhibits the release of lysosomal enzymes. Baicalein is a potent anti-inflammatory and anti-tumor agent, and it blocks PREP (prolyl oligopeptidase). Baicalein induces the S-phase arrest and apoptosis in proliferation of human lung squamous carcinoma CH27 cells. The declining expression of cdk1, cdk2, cyclin D2 and cyclin A by Baicalein resulted in the G1 and G2 cell cycle arrest in C6 rat glioma cells. Baicalein has anti-thrombotic, antiproliferative and anti-mitogenic effects. Baicalein inhibits protein tyrosine kinase in leukemia (CEM) cells and PMA-stimulated PKC (protein kinase C). Baicalein is an inhibitor of 15-LO and CYP2C9.An inhibitor of Ca2+ uptake, 5-LO, and 12-LO
Baicalein is a cell-permeable flavone, originally isolated from the roots of Scutellaria baicalensis, that inhibits cellular Ca2+ uptake, calcium mobilization, and adjuvant-induced arthritis. Baicalein has been shown to inhibit platelet 5-LO (5-lipoxygenase) (IC50=9.5 mM) and 12-LO (12-lipoxygenases) (IC50=0.12 mM) and reverse transcriptase. Baicalein reduces leukotriene biosynthesis and inhibits the release of lysosomal enzymes. Baicalein is a potent anti-inflammatory and anti-tumor agent, and it blocks PREP (prolyl oligopeptidase). Baicalein induces the S-phase arrest and apoptosis in proliferation of human lung squamous carcinoma CH27 cells. The declining expression of cdk1, cdk2, cyclin D2 and cyclin A by Baicalein resulted in the G1 and G2 cell cycle arrest in C6 rat glioma cells. Baicalein has anti-thrombotic, antiproliferative and anti-mitogenic effects. Baicalein inhibits protein tyrosine kinase in leukemia (CEM) cells and PMA-stimulated PKC (protein kinase C). Baicalein is an inhibitor of 15-LO and CYP2C9.
An inhibitor of Ca2+ uptake, 5-LO, and 12-LO
规格
别名
三羟黄酮
英文别名
SpecPlus_000758 | Spectrum5_001418 | W-202870 | baicalein | BAICALEIN [WHO-DD] | MFCD00017459 | SDCCGMLS-0066744.P001 | NCGC00025282-01 | NCGC00025282-02 | NCGC00025282-03 | BAICALEIN [INCI] | Baicalein, 98% | HMS3412F14 | HMS3655P18 | MLS002473007 | NCGC
规格或纯度
Moligand™, 分析标准品, ≥98%
英文名称
Baicalein
生化机理
中药类黄酮的组成成分，黄芩的主要黄酮，抑制花生四烯酸代谢中的12-脂肪氧化酶路径（12-lipoxygenase ，12-LOX），此路径能抑制癌细胞的增殖，诱导凋亡途径。
应用
An inhibitor of Ca2+ uptake, 5-LO, and 12-LO
储存条件
2-8°C储存
运输条件
低温运输
纯度
≥98%
名称和识别符
PubChem SID
EC号
637-183-7
分子类型
小分子
IUPAC Name
5,6,7-trihydroxy-2-phenylchromen-4-one
INCHI
1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H
InChi Key
FXNFHKRTJBSTCS-UHFFFAOYSA-N
Smiles
C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)O)O
Isomeric SMILES
C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)O)O
分子量
270.24
Beilstein号
272683
Reaxy-Rn
272683
Reaxys-RN link address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=272683&ln=
技术文档
高级数据
系统学分类
分类树（Taxonomy Tree）
| 界（kingdom) | 有机化合物 |
|---|---|
| 超类（Superclass) | 苯丙素类和聚酮类 |
| 类（Class) | 黄酮类化合物 |
| 亚类（Subclass） | 黄酮类 |
| 中间层级节点（Intermediate Tree Nodes） | 暂无 |
| 直接上位类(Direct Parent) | 黄酮类 |
| 其他上位类（Alternative Parents） | 7-羟基黄酮类化合物 6-羟基黄酮类化合物 5-羟基黄酮类化合物 色酮 吡喃酮及其衍生物 1-羟基-4-未取代苯类化合物 1-羟基-2-未取代苯类化合物 苯及其取代衍生物 乙烯基酸 杂芳族化合物 多元醇 氧环化合物 有机氧化物 碳氢化合物衍生物 |
| 分子骨架（Molecular Framework) | 芳香族杂多环化合物 |
| 取代基（Substituents） | 1-苯并吡喃 - 1-羟基-2-未取代苯环化合物 - 1-羟基-4-未取代苯环化合物 - 5-羟基黄酮 - 6-羟基黄酮 - 7-羟基黄酮 - 芳香族杂多环化合物 - 苯基化合物 - 苯并吡喃 - 苯并吡喃 - 黄酮 - 杂芳香族化合物 - 烃衍生物 - 羟基黄酮 - 单环苯基基团 - 有机氧化物 - 有机氧化合物 - 有机杂环化合物 - 有机氧化合物 - 氧杂环 - 多醇 - 吡喃 - 吡喃酮 - 乙烯基羧酸 |
| 描述（Description） | 该化合物属于黄酮类有机化合物。这类黄酮类化合物以2-苯基苯并吡喃-4-酮（2-苯基-1-苯并吡喃-4-酮）为骨架结构。 |
| 外部描述符（External Descriptors） | a flavone |
三维结构
交互式化学结构模型
关联靶点（人）
CYP1A2
Tchem
细胞色素 P450 1A2(Cytochrome P450 1A2)
(1 活性数据)
CYP1B1
Tchem
细胞色素 P450 1B1(Cytochrome P450 1B1)
(1 活性数据)
ALOX12
Tchem
花生四烯酸12-脂氧合酶，12S型(Arachidonate 12-lipoxygenase, 12S-type)
(1 活性数据)
ALOX15
Tchem
花生四烯酸15-脂氧合酶(Arachidonate 15-lipoxygenase)
(1 活性数据)
MGAM
Tclin
Maltase-glucoamylase
(654 活性数据)
ESR1
Tclin
Estrogen receptor alpha
(17718 活性数据)
NR3C1
Tclin
Glucocorticoid receptor
(14987 活性数据)
PGR
Tclin
Progesterone receptor
(8562 活性数据)
ALOX5
Tclin
Arachidonate 5-lipoxygenase
(6568 活性数据)
AR
Tclin
Androgen Receptor
(11781 活性数据)
ACHE
Tclin
Acetylcholinesterase
(18204 活性数据)
XDH
Tclin
Xanthine dehydrogenase
(1038 活性数据)
ABAT
Tclin
Gamma-amino-N-butyrate transaminase
(140 活性数据)
KCNH2
Tclin
HERG
(29587 活性数据)
CACNA1C
Tclin
Voltage-gated L-type calcium channel alpha-1C subunit
(766 活性数据)
TNF
Tclin
TNF-alpha
(1897 活性数据)
MME
Tclin
Neprilysin
(838 活性数据)
ANPEP
Tchem
Aminopeptidase N
(863 活性数据)
THRB
Tclin
Thyroid hormone receptor beta-1
(7926 活性数据)
JUN
Tchem
Proto-oncogene c-JUN
(434 活性数据)
CYP1B1
Tchem
Cytochrome P450 1B1
(1148 活性数据)
KCNA5
Tclin
Voltage-gated potassium channel subunit Kv1.5
(1353 活性数据)
NEU2
Tbio
Sialidase 2
(382 活性数据)
ALB
Tchem
Serum albumin
(2651 活性数据)
GBA1
Tclin
Beta-glucocerebrosidase
(14647 活性数据)
PIM1
Tchem
Serine/threonine-protein kinase PIM1
(9629 活性数据)
PLK1
Tchem
Serine/threonine-protein kinase PLK1
(28605 活性数据)
ALOX15B
Tchem
Arachidonate 15-lipoxygenase, type II
(7244 活性数据)
GAA
Tclin
Lysosomal alpha-glucosidase
(35701 活性数据)
CYP1A1
Tchem
Cytochrome P450 1A1
(1169 活性数据)
ALDH1A1
Tchem
Aldehyde dehydrogenase 1A1
(77053 活性数据)
ALOX12
Tchem
Arachidonate 12-lipoxygenase
(3262 活性数据)
DAPK1
Tchem
Death-associated protein kinase 1
(1664 活性数据)
CYP2D6
Tclin
Cytochrome P450 2D6
(33882 活性数据)
FBP1
Tchem
Fructose-1,6-bisphosphatase
(1199 活性数据)
HSD17B3
Tchem
Estradiol 17-beta-dehydrogenase 3
(821 活性数据)
HBB
Tbio
Hemoglobin beta chain
(329 活性数据)
SI
Tchem
Sucrase-isomaltase
(84 活性数据)
ALOX15
Tchem
Arachidonate 15-lipoxygenase
(7108 活性数据)
CYP1A2
Tchem
Cytochrome P450 1A2
(26471 活性数据)
AKT1
Tchem
Serine/threonine-protein kinase AKT
(9192 活性数据)
FLT3
Tclin
Tyrosine-protein kinase receptor FLT3
(13481 活性数据)
SELL
Tchem
Leukocyte adhesion molecule-1
(145 活性数据)
PIN1
Tchem
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1
(36611 活性数据)
CYP2C9
Tchem
Cytochrome P450 2C9
(32119 活性数据)
CYP2C19
Tchem
Cytochrome P450 2C19
(29246 活性数据)
CYP3A4
Tclin
Cytochrome P450 3A4
(53859 活性数据)
YES1
Tclin
Tyrosine-protein kinase YES
(2781 活性数据)
TP53
Tchem
Cellular tumor antigen p53
(48468 活性数据)
C8166
(1658 活性数据)
DU-145
(51482 活性数据)
HL-60
(67320 活性数据)
HT-29
(80576 活性数据)
Huh-7
(12904 活性数据)
关联靶点（其它种属）
Htr7
Serotonin 7 (5-HT7) receptor (19 活性数据)
Glo1
Glyoxalase I (4 活性数据)
Trypsin (394 活性数据)
Cruzipain (33337 活性数据)
DPP4
Dipeptidyl peptidase IV (11 活性数据)
Sele
Selectin E (1 活性数据)
Selp
P-selectin (7 活性数据)
PREP
Prolyl endopeptidase (14 活性数据)
Abcb1b
P-glycoprotein 1 (174 活性数据)
Hdac6
Histone deacetylase 6 (222 活性数据)
pol
Human immunodeficiency virus type 1 integrase (9041 活性数据)
Pseudomonas aeruginosa (123386 活性数据)
Salmonella typhimurium (15756 活性数据)
Staphylococcus aureus (210822 活性数据)
Mycobacterium tuberculosis (203094 活性数据)
Pichia kudriavzevii (7448 活性数据)
Aspergillus fumigatus (16427 活性数据)
Cryptococcus neoformans (21258 活性数据)
Candida albicans (78123 活性数据)
Nakaseomyces glabratus (9108 活性数据)
Candida parapsilosis (8521 活性数据)
Candida tropicalis (8381 活性数据)
Trichophyton rubrum (3646 活性数据)
Rattus norvegicus (775804 活性数据)
Human immunodeficiency virus 1 (70413 活性数据)
West Nile virus (623 活性数据)
Hepatitis C virus (23859 活性数据)
3T3-L1 (3664 活性数据)
RAW264.7 (28094 活性数据)
RBL-2H3 (1162 活性数据)
Vero (26788 活性数据)
Calf thymus DNA (4845 活性数据)
Urease (750 活性数据)
lef
Anthrax lethal factor (7585 活性数据)
Avian myoblastosis virus polyprotein II (68 活性数据)
Dengue virus type 2 NS3 protein (2214 活性数据)
Dyrk1a
Dual specificity tyrosine-phosphorylation-regulated kinase 1A (1629 活性数据)
rep
Replicase polyprotein 1ab (378 活性数据)
pfk
6-phospho-1-fructokinase (7870 活性数据)
ddn
Putative uncharacterized protein (49 活性数据)
BCHE
Cholinesterase (8742 活性数据)
Danio rerio (3092 活性数据)
dengue virus type 2 (2400 活性数据)
Spodoptera litura (1708 活性数据)
Trichophyton mentagrophytes (4846 活性数据)
Mapt
Microtubule-associated protein tau (6 活性数据)
Rorc
Nuclear receptor ROR-gamma (89407 活性数据)
fba
Putative fructose-1,6-bisphosphate aldolase (15559 活性数据)
ffp
4'-phosphopantetheinyl transferase ffp (24982 活性数据)
Ntrk2
BDNF/NT-3 growth factors receptor (124 活性数据)
作用机制
| 作用机制 | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | 参考文献 |
|---|
化学和物理性质
溶解性
Soluble in alcohol, methanol, ether, acetone, ethyl acetate, hot glacial acetic acid, dilute sodium hydroxide, and DMSO (50 mM). Insoluble in water
密度
1.548
敏感性
对光和热敏感
熔点
256-271°C
分子量
270.240 g/mol
XLogP3
1.700
氢键供体数Hydrogen Bond Donor Count
3
氢键受体数Hydrogen Bond Acceptor Count
5
可旋转键计数Rotatable Bond Count
1
精确质量Exact Mass
270.053 Da
单同位素质量Monoisotopic Mass
270.053 Da
拓扑极表面积Topological Polar Surface Area
87.000 Ų
重原子数Heavy Atom Count
20
形式电荷Formal Charge
0
复杂度Complexity
412.000
同位素原子数Isotope Atom Count
0
定义的原子立体中心计数Defined Atom Stereocenter Count
0
未定义的原子立体中心计数Undefined Atom Stereocenter Count
0
定义的键立体中心计数Defined Bond Stereocenter Count
0
未定义的键立体中心计数Undefined Bond Stereocenter Count
0
所有立体化学键的总数The total count of all stereochemical bonds
0
共价键合单元计数Covalently-Bonded Unit Count
1
安全和危险性（GHS）
象形图
信号词
警告
危险声明
H315: 引起皮肤刺激
H319: 引起严重眼睛刺激
H335: 可能引起呼吸道刺激
预防措施声明
P261: 避免吸入灰尘/烟雾/气体/雾/蒸汽/喷雾
P264: 处理后要彻底洗手。
P271: 仅在室外或通风良好的地方使用。
P280: 戴防护手套/穿防护服/戴防护眼罩/戴防护面具。
P321: 特殊处理（请参阅此标签上的...）。
P302+P352: 如皮肤沾染：用水充分清洗。
P304+P340: 如误吸入：将人转移到空气新鲜处，保持呼吸舒适体位。
P305+P351+P338: 如进入眼睛：用水小心冲洗几分钟。如戴隐形眼镜并可方便地取出，取出隐形眼镜。继续冲洗。
P362+P364: 脱掉沾污的衣服，清洗后方可重新使用。
P405: 密闭存放
P403+P233: 存放在通风良好的地方。保持容器密闭。
P501: 将内容物/容器处理到。。。
P264+P265: 处理后彻底洗手[和…]。不要触摸眼睛。
P337+P317: 如果眼睛刺激持续：寻求医疗帮助。
P332+P317: 如果出现皮肤刺激：请寻求医疗帮助。
P319: 如果你感到不适，请寻求医疗帮助。
WGK Germany
3
RTECS
DJ3100898
Merck Index
942
个人防护装备
dust mask type N95 (US),Eyeshields,Gloves
质检证书（CoA,COO,BSE/TSE 和分析图谱)
技术文档和文章
Mechanisms of Gut Microbial Enzyme-Mediated Metabolism of Glucuronide Conjugates and Drug Biotransformation
目录： 技术文章
Mechanisms by Which Flavonoid Natural Products Regulate the Oxidative Stress-Inflammation Axis
目录： 技术文章
此产品的引用文献
引用文献
| 1. Lei Liu, Yingyu Sima, Jinxia Feng, Shuting Shi, Aiting Chen, Chuanqin Zhou, Quanguo He, Yimin Tan. (2023) Bismuth oxide and nitrogen-doped reduced graphene oxide co-modified glassy carbon electrode to perform sensitive electrochemical sensing and determination of chrysin in pharmaceutical capsules. MICROCHEMICAL JOURNAL, [10.1016/j.microc.2023.109544] |
| 2. Yongbing Xu, Yawen Li, Guilin Chen, Minxia Fan, Guangwan Hu, Mingquan Guo. (2023) Screening and identification of potential hypoglycemic and hypolipidemic compounds from aqueous extract of Scutellaria baicalensis Georgi root combing affinity ultrafiltration with multiple drug targets and in silico analysis. PHYTOCHEMICAL ANALYSIS, [PMID:37779216] [10.1002/pca.3285] |
| 3. Chuanyi Gu, Chunru Wang, Wenjie Ma, Yunli Gao, Junyao Li, Qing Jin, Xiaochen Wu. (2023) Drug-Loaded Konjac Glucomannan/Metal–Organic Framework Composite Hydrogels as Antibacterial and Anti-Inflammatory Cell Scaffolds. ACS Applied Materials & Interfaces, [PMID:37632730] [10.1021/acsami.3c06996] |
| 4. Shuting Shi, Yanping Wei, Jinxia Feng, Chuanqin Zhou, Jinsong Zuo, Liangyuan Yao, Jianhua Ding, Kanghua Li, Quanguo He. (2023) Facile and ultrasensitive electrochemical detection of baicalein on bismuth oxide-carboxylated multi-walled carbon nanotube/glassy carbon electrode. JOURNAL OF FOOD COMPOSITION AND ANALYSIS, [10.1016/j.jfca.2023.105557] |
| 5. Yufeng Chen, Guobin Xia, Chunfeng Wang, Huawei Wu, Xiaogang Xu, Genxiang Mao, Jiong Wu, Zhenlei Zhao. (2023) Impact of dietary plant flavonoids on 7,8-dihydroxyflavone transepithelial transport in human intestinal Caco-2 cells. Food Science & Nutrition, [PMID:37970375] [10.1002/fsn3.3581] |
| 6. Xin Liu, Wei Niu, Jiamin Liu, Zhao Cui, Jiazheng Li, Zhenhai Zhang, Jianming Ju. (2023) Preparation of β-cyclodextrin and hydroxypropyl-β-cyclodextrin inclusion complexes of baicalein and evaluation of their effects on dextran sulfate sodium-induced acute ulcerative colitis in mice. JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY, [10.1016/j.jddst.2023.104714] |
| 7. Liao Zhenkun, Liu Xiaojuan, Zheng Juan, Zhao Chenning, Wang Dengliang, Xu Yang, Sun Chongde. (2023) A multifunctional true caffeoyl coenzyme A O-methyltransferase enzyme participates in the biosynthesis of polymethoxylated flavones in citrus. PLANT PHYSIOLOGY, [PMID:37086474] [10.1093/plphys/kiad249] |
| 8. Yameng Liu. (2023) Detection of LPS-induced macrophage activation with single-cell resolution through DC insulator-based electrokinetic devices. ELECTROPHORESIS, [PMID:36996424] [10.1002/elps.202200274] |
| 9. Xin-Mei Xie, Jiao-Jiao Hao, Jun-Zhuo Shi, Yun-Feng Zhou, Peng-Fei Liu, Feng Wang, Xiao-Ming Zheng, Xiu-Ying Yu, Chen-Chen Wang, Yi Yan, Guan-Hua Du, Jun-Ke Song, Yang-Yang He, Xiao-Bin Pang. (2023) Baicalein ameliorates Alzheimer's disease via orchestration of CX3CR1/NF-κB pathway in a triple transgenic mouse model. INTERNATIONAL IMMUNOPHARMACOLOGY, [PMID:37098656] [10.1016/j.intimp.2023.109994] |
| 10. Shuoshuo Yang, Guoqi Ni, Mengyang Xia, Hailing Li, Zhonghong Gao. (2022) Mussel inspired multifunctional bovine serum albumin (BSA) coatings loaded with Baicalein (BAI) to enhance osteogenesis and resist oxidative stress for potential application on implant. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:36586655] [10.1016/j.ijbiomac.2022.12.285] |
| 11. Mang-Mang Li, Yi-Ting Chen, Jin-Cang Ruan, Wen-Jun Wang, Ji-Guang Chen, Qing-Feng Zhang. (2022) Structure-activity relationship of dietary flavonoids on pancreatic lipase. Current Research in Food Science, [PMID:36618100] [10.1016/j.crfs.2022.100424] |
| 12. Zeng Wanying, Liu Xiaojing, Wu Yangyang, Cai Yuting, Li Zhennan, Ye Fei, Sun Yuanhong, Li Feng, Xing Huijie, Wang Shuai. (2022) Dysregulated hepatic UDP-glucuronosyltransferases and flavonoids glucuronidation in experimental colitis. Frontiers in Pharmacology, [PMID:36408246] [10.3389/fphar.2022.1053610] |
| 13. Jingyi Hu, Yiheng Tong, Zhaofeng Shen, Yanan Li, Cheng Cheng, Ryan Au, Feng Xu, Yajun Liu, Lei Zhu, Hong Shen. (2022) Gegen Qinlian decoction ameliorates murine colitis by inhibiting the expansion of Enterobacteriaceae through activating PPAR-γ signaling. BIOMEDICINE & PHARMACOTHERAPY, [PMID:36007273] [10.1016/j.biopha.2022.113571] |
| 14. Zhi-Ang Liu, Ya-Nan Zuo, Yinghui Xia, Jing Sun, Shuyun Zhu. (2022) Enhanced detection of ascorbic acid with cascaded fluorescence recovery of a dual-nanoquencher system. Analytical Methods, 14 (37): (3632-3637). [PMID:36052693] [10.1039/D2AY01019D] |
| 15. Zou Linghui, Zhang Zhongbin, Chen Jinqing, Yang Xu, Li Yuyang, Tang Jing, Du Xiaolu, Tang Ling, Liang Dan, Zhu Xiaoyong, Feng Jianfang, Ding Wenya. (2022) β-Cyclodextrin-Grafted Chitosan Enhances Intestinal Drug Absorption and Its Preliminary Mechanism Exploration. AAPS PHARMSCITECH, 23 (6): (1-11). [PMID:35948815] [10.1208/s12249-022-02380-z] |
| 16. Jie Zhao, Lin Huang, Renjie Li, Zhuangwei Zhang, Jin Chen, Hongjin Tang. (2022) Insights from multi-spectroscopic analysis and molecular modeling to understand the structure–affinity relationship and the interaction mechanism of flavonoids with gliadin. Food & Function, 13 (9): (5061-5074). [PMID:35404372] [10.1039/D1FO03816H] |
| 17. Feng-wei Zhang, Li-yang Peng, Chuan-Jian Shi, Jian-chi Li, Feng-xiang Pang, Wei-ming Fu, Xiao-hua Pan, Jin-fang Zhang. (2022) Baicalein mediates the anti-tumor activity in Osteosarcoma through lncRNA-NEF driven Wnt/β-catenin signaling regulatory axis. Journal of Orthopaedic Translation, [PMID:35330943] [10.1016/j.jot.2021.12.001] |
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