Isosilybin (BioDeep_00000004182)

 

Secondary id: BioDeep_00000270382

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-Benzopyran-4-one, 2-(2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-

化学式: C25H22O10 (482.1213)
中文名称: 异水飞蓟宾
谱图信息: 最多检出来源 Homo sapiens(otcml) 13.21%

分子结构信息

SMILES: COc(c(O)5)cc(cc5)C(O1)C(CO)Oc(c2)c(ccc2[C@@H](O3)[C@@H](O)C(=O)c(c(O)4)c(cc(O)c4)3)1
InChI: InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3

描述信息

Constituent of Silybum marianum (milk thistle). Isosilybin is found in coffee and coffee products and green vegetables.
Isosilybin is found in coffee and coffee products. Isosilybin is a constituent of Silybum marianum (milk thistle)
Isosilybin is a natural product found in Silybum with data available.
[Raw Data] CBA83_Isosilybin-B_pos_20eV.txt
[Raw Data] CBA83_Isosilybin-B_neg_30eV.txt
[Raw Data] CBA83_Isosilybin-B_neg_20eV.txt
[Raw Data] CBA83_Isosilybin-B_pos_10eV.txt
[Raw Data] CBA83_Isosilybin-B_pos_40eV.txt
[Raw Data] CBA83_Isosilybin-B_neg_10eV.txt
[Raw Data] CBA83_Isosilybin-B_pos_50eV.txt
[Raw Data] CBA83_Isosilybin-B_pos_30eV.txt
[Raw Data] CBA83_Isosilybin-B_neg_50eV.txt
[Raw Data] CBA83_Isosilybin-B_neg_40eV.txt
Isosilybin (Isosilybinin) is a flavonoid from Silybum marianum; inhibits CYP3A4 induction with an IC50 of 74 μM.
Isosilybin (Isosilybinin) is a flavonoid from Silybum marianum; inhibits CYP3A4 induction with an IC50 of 74 μM.

同义名列表

9 个代谢物同义名

4H-1-Benzopyran-4-one, 2-(2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-; 3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one; 3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-1-benzopyran-4-one; 3,5,7-Trihydroxy-2-(2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one; Silymarin (Silybin B); Isosilybinin; Isosilybin; isosilybin B; Isosilybin



数据库引用编号

29 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

5 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 10 CASP3, CCR1, CD36, CYP3A4, EGFR, HPGDS, PNPLA3, PRKAA2, SREBF1, TNK1
Peripheral membrane protein 2 CYP1B1, TNK1
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 6 CYP1B1, CYP3A4, EGFR, HMOX1, PNPLA3, SREBF1
Nucleus 8 CASP3, EGFR, GABPA, HMOX1, NR1I2, PPARA, PRKAA2, SREBF1
cytosol 8 ACOX1, AKR1C2, CASP3, HMOX1, HPGDS, MTTP, PRKAA2, SREBF1
dendrite 1 PRKAA2
nuclear body 1 NR1I2
phagocytic vesicle 1 CD36
nucleoplasm 8 CASP3, GABPA, HMOX1, HPGDS, NR1I2, PPARA, PRKAA2, SREBF1
Cell membrane 3 CCR1, CD36, EGFR
Cytoplasmic side 1 HMOX1
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Multi-pass membrane protein 3 CCR1, CD36, SREBF1
Golgi apparatus membrane 1 SREBF1
cell junction 1 EGFR
cell surface 2 CD36, EGFR
glutamatergic synapse 2 CASP3, EGFR
Golgi apparatus 3 CD36, MTTP, PRKAA2
Golgi membrane 2 EGFR, SREBF1
lysosomal membrane 1 EGF
neuronal cell body 2 CASP3, PRKAA2
Cytoplasm, cytosol 1 AKR1C2
endosome 1 EGFR
plasma membrane 5 CCR1, CD36, EGF, EGFR, TNK1
Membrane 10 ACOX1, CD36, CYP1B1, CYP3A4, EGF, EGFR, HMOX1, PNPLA3, PRKAA2, TNK1
apical plasma membrane 2 CD36, EGFR
axon 2 CCK, PRKAA2
basolateral plasma membrane 2 EGFR, MTTP
caveola 1 CD36
extracellular exosome 1 EGF
endoplasmic reticulum 3 HMOX1, MTTP, SREBF1
extracellular space 5 CCK, CD36, EGF, EGFR, HMOX1
perinuclear region of cytoplasm 2 EGFR, HMOX1
mitochondrion 1 CYP1B1
protein-containing complex 2 EGFR, SREBF1
intracellular membrane-bounded organelle 3 CYP1B1, CYP3A4, HPGDS
Microsome membrane 2 CYP1B1, CYP3A4
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 EGFR
Secreted 1 CCK
extracellular region 2 CCK, EGF
mitochondrial outer membrane 1 HMOX1
transcription regulator complex 1 NR1I2
nuclear membrane 1 EGFR
external side of plasma membrane 2 CCR1, CD36
Single-pass type II membrane protein 1 PNPLA3
vesicle 1 MTTP
Apical cell membrane 1 CD36
Membrane raft 2 CD36, EGFR
focal adhesion 1 EGFR
Peroxisome 1 ACOX1
collagen trimer 1 CD36
intracellular vesicle 1 EGFR
peroxisomal matrix 1 ACOX1
peroxisomal membrane 1 ACOX1
nuclear speck 1 PRKAA2
receptor complex 3 CD36, EGFR, MTTP
chromatin 4 GABPA, NR1I2, PPARA, SREBF1
cell periphery 1 CD36
brush border membrane 2 CD36, MTTP
microvillus membrane 1 MTTP
nuclear envelope 1 SREBF1
Lipid droplet 1 PNPLA3
Cytoplasmic vesicle membrane 1 SREBF1
specific granule membrane 1 CD36
cytoplasmic stress granule 1 PRKAA2
intermediate filament cytoskeleton 1 NR1I2
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
endoplasmic reticulum lumen 1 MTTP
platelet alpha granule lumen 1 EGF
endocytic vesicle membrane 1 CD36
Single-pass type IV membrane protein 1 HMOX1
ER to Golgi transport vesicle membrane 1 SREBF1
clathrin-coated endocytic vesicle membrane 2 EGF, EGFR
death-inducing signaling complex 1 CASP3
nucleotide-activated protein kinase complex 1 PRKAA2
platelet alpha granule membrane 1 CD36
Cytoplasmic vesicle, COPII-coated vesicle membrane 1 SREBF1
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Sterol regulatory element-binding protein 1]: Endoplasmic reticulum membrane 1 SREBF1
[Processed sterol regulatory element-binding protein 1]: Nucleus 1 SREBF1
[Isoform SREBP-1aDelta]: Nucleus 1 SREBF1
[Isoform SREBP-1cDelta]: Nucleus 1 SREBF1


文献列表

  • Xueyun Liu, Man Hu, Chen Ye, Lihong Liao, Chang Ding, Lijuan Sun, Jichao Liang, Yong Chen. Isosilybin regulates lipogenesis and fatty acid oxidation via the AMPK/SREBP-1c/PPARα pathway. Chemico-biological interactions. 2022 Dec; 368(?):110250. doi: 10.1016/j.cbi.2022.110250. [PMID: 36347319]
  • Shabana Bibi, Katsumi Sakata. An Integrated Computational Approach for Plant-Based Protein Tyrosine Phosphatase Non-Receptor Type 1 Inhibitors. Current computer-aided drug design. 2017 Nov; 13(4):319-335. doi: 10.2174/1573409913666170406145607. [PMID: 28382867]
  • Reza Keshavarz Afshar, Mohammad Reza Chaichi, Mahya Ansari Jovini, Emad Jahanzad, Masoud Hashemi. Accumulation of silymarin in milk thistle seeds under drought stress. Planta. 2015 Sep; 242(3):539-43. doi: 10.1007/s00425-015-2265-9. [PMID: 25708739]
  • Kim D Mooiman, Roel F Maas-Bakker, Ed E Moret, Jos H Beijnen, Jan H M Schellens, Irma Meijerman. Milk thistle's active components silybin and isosilybin: novel inhibitors of PXR-mediated CYP3A4 induction. Drug metabolism and disposition: the biological fate of chemicals. 2013 Aug; 41(8):1494-504. doi: 10.1124/dmd.113.050971. [PMID: 23674609]
  • Masumeh Khalili, Tahereh Hasanloo, Seyyed Kamal Kazemi Tabar, Hassan Rahnama. Influence of exogenous salicylic acid on flavonolignans and lipoxygenase activity in the hairy root cultures of Silybum marianum. Cell biology international. 2009 Sep; 33(9):988-94. doi: 10.1016/j.cellbi.2009.06.003. [PMID: 19524695]
  • Sz Nyiredy, Zs Samu, Z Szücs, K Gulácsi, T Kurtán, S Antus. New insight into the biosynthesis of flavanolignans in the white-flowered variant of Silybum marianum. Journal of chromatographic science. 2008 Feb; 46(2):93-6. doi: 10.1093/chromsci/46.2.93. [PMID: 18366865]
  • James I Lee, Mahesh Narayan, Jeffrey S Barrett. Analysis and comparison of active constituents in commercial standardized silymarin extracts by liquid chromatography-electrospray ionization mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Jan; 845(1):95-103. doi: 10.1016/j.jchromb.2006.07.063. [PMID: 16942922]
  • James I Lee, Bih H Hsu, Di Wu, Jeffrey S Barrett. Separation and characterization of silybin, isosilybin, silydianin and silychristin in milk thistle extract by liquid chromatography-electrospray tandem mass spectrometry. Journal of chromatography. A. 2006 May; 1116(1-2):57-68. doi: 10.1016/j.chroma.2006.03.053. [PMID: 16631762]
  • Zsuzsanna Samu, Szabolcs Nyiredy, Eszter Baitz-Gács, Zsuzsa Varga, Tibor Kurtán, Zoltán Dinya, Sándor Antus. Structure elucidation and antioxidant activity of (-)-isosilandrin isolated from Silybum marianum L. Chemistry & biodiversity. 2004 Nov; 1(11):1668-77. doi: 10.1002/cbdv.200490125. [PMID: 17191807]
  • E Bosisio, C Benelli, O Pirola. Effect of the flavanolignans of Silybum marianum L. on lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes. Pharmacological research. 1992 Feb; 25(2):147-54. doi: 10.1016/1043-6618(92)91383-r. [PMID: 1635893]
  • T Philipp, A M Sharma, H M Thiede, A Kribben. Sympathetic nervous activity and noradrenaline reactivity during angiotensin converting enzyme inhibition. The American journal of cardiology. 1987 Apr; 59(10):55D-59D. doi: 10.1016/0002-9149(87)90054-3. [PMID: 3034034]
  • A F Attili, D Autizi, L Capocaccia. Rapid determination of plasma ammonia using an ion specific electrode. Biochemical medicine. 1975 Sep; 14(1):109-16. doi: 10.1016/0006-2944(75)90025-3. [PMID: 2165]
  • W Dobryszycka, J Kulpa, A Woytoń, J Woytoń, J Szacki, A Dzioba. Influence of industrial toxic compounds on pregnancy. VI. Some tissue enzymes in pregnant guinea pigs exposed to the action of triethylenetetramine. Archivum immunologiae et therapiae experimentalis. 1975; 23(6):867-70. doi: . [PMID: 4046]