Cirsiliol (BioDeep_00000007762)

Main id: BioDeep_00000270028

 

human metabolite PANOMIX_OTCML-2023 blood metabolite natural product


代谢物信息卡片


2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one

化学式: C17H14O7 (330.0739)
中文名称: 条叶蓟素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1(OC)=CC2OC(C3C=CC(O)=C(O)C=3)=CC(=O)C=2C(O)=C1OC
InChI: InChI=1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3

描述信息

Cirsiliol, also known as 3,4,5-trihydroxy-6,7-dimethoxyflavone or 6,7-dimethoxy-5,3,4-trihydroxyflavone, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, cirsiliol is considered to be a flavonoid lipid molecule. Cirsiliol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cirsiliol can be found in common sage and lemon verbena, which makes cirsiliol a potential biomarker for the consumption of these food products.
Cirsiliol is a potent and selective 5-lipoxygenase inhibitor and a competitive low affinity benzodiazepine receptor ligand.
Cirsiliol is a potent and selective 5-lipoxygenase inhibitor and a competitive low affinity benzodiazepine receptor ligand.
Cirsiliol is a potent and selective 5-lipoxygenase inhibitor and a competitive low affinity benzodiazepine receptor ligand.

同义名列表

6 个代谢物同义名

2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one; 3,4,5-trihydroxy-6,7-dimethoxy-flavone; 6,7-Dimethoxy-5,3,4-trihydroxyflavone; 3,4,5-trihydroxy-6,7-dimethoxyflavone; Cirsiliol; Cirsiliol



数据库引用编号

18 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)

164 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 13 ALOX5, BNIP3, CASP3, CDH1, CDH2, FOXO1, JAK2, PIK3C3, PINK1, STAT3, TYK2, TYR, XDH
Peripheral membrane protein 3 ALOX5, CYP1B1, JAK2
Endosome membrane 1 NOTCH1
Endoplasmic reticulum membrane 3 BNIP3, CYP1B1, NOTCH1
Mitochondrion membrane 1 BNIP3
Cytoplasmic vesicle, autophagosome 1 PIK3C3
Nucleus 9 BNIP3, CASP3, CDH1, FOXO1, JAK2, NOTCH1, PINK1, STAT3, TYK2
autophagosome 1 PIK3C3
cytosol 12 ALOX5, CASP3, CDH1, FOXO1, JAK2, NOTCH1, PIK3C3, PINK1, SOCS3, STAT3, TYK2, XDH
dendrite 2 BNIP3, IL6ST
mitochondrial membrane 1 BNIP3
phosphatidylinositol 3-kinase complex, class III 1 PIK3C3
trans-Golgi network 1 CDH1
nucleoplasm 8 ALOX5, BNIP3, CASP3, CDH1, FOXO1, JAK2, NOTCH1, STAT3
RNA polymerase II transcription regulator complex 1 STAT3
Cell membrane 4 CDH1, CDH2, IL6ST, NOTCH1
lamellipodium 2 CDH1, CDH2
Multi-pass membrane protein 1 FUNDC1
cell junction 2 CDH1, CDH2
cell surface 2 CDH2, NOTCH1
glutamatergic synapse 5 CASP3, CDH1, JAK2, NOTCH1, PIK3C3
Golgi apparatus 1 CDH1
Golgi membrane 1 NOTCH1
growth cone 1 PINK1
mitochondrial inner membrane 2 ATP5ME, PINK1
neuronal cell body 2 CASP3, IL6ST
postsynapse 2 CDH1, JAK2
sarcolemma 1 CDH2
Cytoplasm, cytosol 2 ALOX5, PINK1
Lysosome 1 TYR
acrosomal vesicle 1 NOTCH1
endosome 2 CDH1, PIK3C3
plasma membrane 7 CDH1, CDH2, IL6ST, JAK2, NOTCH1, STAT3, TYK2
Membrane 10 BNIP3, CDH1, CDH2, CYP1B1, IL6ST, JAK2, NOTCH1, PIK3C3, PINK1, TYK2
apical plasma membrane 2 CDH2, NOTCH1
axon 2 CCK, PINK1
basolateral plasma membrane 1 CDH2
caveola 1 JAK2
extracellular exosome 3 CDH1, IL6ST, TYK2
endoplasmic reticulum 3 BNIP3, NOTCH1, PINK1
extracellular space 4 ALOX5, CCK, IL6ST, XDH
perinuclear region of cytoplasm 4 ALOX5, CDH1, PINK1, TYR
Schaffer collateral - CA1 synapse 1 NOTCH1
adherens junction 3 CDH1, CDH2, NOTCH1
apicolateral plasma membrane 1 CDH2
intercalated disc 1 CDH2
mitochondrion 6 ATP5ME, BNIP3, CYP1B1, FOXO1, FUNDC1, PINK1
intracellular membrane-bounded organelle 2 CYP1B1, TYR
Microsome membrane 1 CYP1B1
postsynaptic density 3 BNIP3, CASP3, CDH2
Single-pass type I membrane protein 5 CDH1, CDH2, IL6ST, NOTCH1, TYR
Secreted 1 CCK
extracellular region 5 ALOX5, CCK, CDH1, IL6ST, NOTCH1
cytoplasmic side of plasma membrane 4 CDH1, JAK2, SOCS3, TYK2
Mitochondrion outer membrane 2 FUNDC1, PINK1
Single-pass membrane protein 2 BNIP3, PINK1
mitochondrial outer membrane 3 BNIP3, FUNDC1, PINK1
[Isoform 2]: Secreted 1 IL6ST
transcription regulator complex 1 STAT3
Nucleus membrane 1 ALOX5
nuclear membrane 2 ALOX5, CDH1
external side of plasma membrane 1 IL6ST
actin cytoskeleton 1 CDH1
Melanosome membrane 1 TYR
midbody 1 PIK3C3
apical part of cell 1 CDH2
cell-cell junction 1 CDH2
Golgi-associated vesicle 1 TYR
presynaptic active zone membrane 1 CDH2
Cell membrane, sarcolemma 1 CDH2
Cytoplasm, perinuclear region 1 ALOX5
Mitochondrion inner membrane 1 PINK1
Membrane raft 2 IL6ST, JAK2
focal adhesion 2 CDH2, JAK2
GABA-ergic synapse 1 PIK3C3
Cell junction, adherens junction 2 CDH1, CDH2
flotillin complex 1 CDH1
Peroxisome 2 PIK3C3, XDH
sarcoplasmic reticulum 1 XDH
mitochondrial intermembrane space 1 PINK1
collagen-containing extracellular matrix 1 CDH2
fascia adherens 1 CDH2
lateral plasma membrane 1 CDH1
axoneme 1 PIK3C3
Late endosome 1 PIK3C3
receptor complex 2 IL6ST, NOTCH1
neuron projection 1 CDH2
chromatin 3 FOXO1, PINK1, STAT3
Late endosome membrane 1 NOTCH1
phagocytic vesicle membrane 1 PIK3C3
cytoskeleton 3 JAK2, PINK1, TYK2
Golgi apparatus, trans-Golgi network 1 CDH1
nuclear envelope 2 ALOX5, BNIP3
Nucleus envelope 1 ALOX5
Endomembrane system 1 JAK2
endosome lumen 1 JAK2
phagophore assembly site 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type I 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type II 1 PIK3C3
Melanosome 1 TYR
euchromatin 1 JAK2
cell body 1 PINK1
plasma membrane raft 1 CDH2
ficolin-1-rich granule lumen 1 ALOX5
secretory granule lumen 1 ALOX5
endoplasmic reticulum lumen 1 CDH2
nuclear matrix 1 ALOX5
phosphatidylinositol 3-kinase complex 1 SOCS3
anaphase-promoting complex 1 CDH1
mitochondrial envelope 1 BNIP3
postsynaptic density membrane 1 NOTCH1
presynaptic endosome 1 PIK3C3
Nucleus matrix 1 ALOX5
nuclear envelope lumen 1 ALOX5
[Isoform 2]: Nucleus 1 CDH1
extrinsic component of cytoplasmic side of plasma membrane 2 JAK2, TYK2
death-inducing signaling complex 1 CASP3
postsynaptic specialization membrane 1 CDH2
apical junction complex 1 CDH1
[Isoform 1]: Cell membrane 1 IL6ST
Lewy body 1 PINK1
Cell junction, desmosome 2 CDH1, CDH2
desmosome 2 CDH1, CDH2
extrinsic component of plasma membrane 2 JAK2, TYK2
granulocyte macrophage colony-stimulating factor receptor complex 1 JAK2
interleukin-12 receptor complex 2 JAK2, TYK2
interleukin-23 receptor complex 2 JAK2, TYK2
catenin complex 2 CDH1, CDH2
proton-transporting ATP synthase complex 1 ATP5ME
postsynaptic endosome 1 PIK3C3
astrocyte projection 1 PINK1
proton-transporting ATP synthase complex, coupling factor F(o) 1 ATP5ME
Autolysosome 1 PIK3C3
interleukin-6 receptor complex 1 IL6ST
ciliary neurotrophic factor receptor complex 1 IL6ST
Nucleus intermembrane space 1 ALOX5
oncostatin-M receptor complex 1 IL6ST
[Notch 1 intracellular domain]: Nucleus 1 NOTCH1
MAML1-RBP-Jkappa- ICN1 complex 1 NOTCH1


文献列表

  • Benedetta Fois, Angela Corona, Enzo Tramontano, Simona Distinto, Elias Maccioni, Rita Meleddu, Pierluigi Caboni, Costantino Floris, Filippo Cottiglia. Flavonoids and Acid-Hydrolysis derivatives of Neo-Clerodane diterpenes from Teucrium flavum subsp. glaucum as inhibitors of the HIV-1 reverse transcriptase-associated RNase H function. Journal of enzyme inhibition and medicinal chemistry. 2021 Dec; 36(1):749-757. doi: 10.1080/14756366.2021.1887170. [PMID: 33715562]
  • Akram Taleghani, Seyed Ahmad Emami, Zahra Tayarani-Najaran. Artemisia: a promising plant for the treatment of cancer. Bioorganic & medicinal chemistry. 2020 01; 28(1):115180. doi: 10.1016/j.bmc.2019.115180. [PMID: 31784199]
  • Wael A Elmasri, Tianjiao Yang, Phat Tran, Mohamed-Elamir F Hegazy, Abdul N Hamood, Yehia Mechref, Paul W Paré. Teucrium polium phenylethanol and iridoid glycoside characterization and flavonoid inhibition of biofilm-forming Staphylococcus aureus. Journal of natural products. 2015 Jan; 78(1):2-9. doi: 10.1021/np5004092. [PMID: 25524452]
  • Peter Forgo, István Zupkó, Judit Molnár, Andrea Vasas, György Dombi, Judit Hohmann. Bioactivity-guided isolation of antiproliferative compounds from Centaurea jacea L. Fitoterapia. 2012 Jul; 83(5):921-5. doi: 10.1016/j.fitote.2012.04.006. [PMID: 22537643]
  • Jun Li, Frank R Fronczek, Daneel Ferreira, Charles L Burandt, Vincent Setola, Bryan L Roth, Jordan K Zjawiony. Bis-spirolabdane diterpenoids from Leonotis nepetaefolia. Journal of natural products. 2012 Apr; 75(4):728-34. doi: 10.1021/np3000156. [PMID: 22475308]
  • Shuangqing Wu, Qun Sun, Chunjun Chu, Jian Zhang. [Chemical constituents of Eupatorium lindleyanum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Apr; 37(7):937-40. doi: . [PMID: 22792793]
  • Anat Elmann, Sharon Mordechay, Hilla Erlank, Alona Telerman, Miriam Rindner, Rivka Ofir. Anti-neuroinflammatory effects of the extract of Achillea fragrantissima. BMC complementary and alternative medicine. 2011 Oct; 11(?):98. doi: 10.1186/1472-6882-11-98. [PMID: 22018032]
  • Gjoshe Stefkov, Svetlana Kulevanova, Biljana Miova, Suzana Dinevska-Kjovkarovska, Per Mølgaard, Anna K Jäger, Knud Josefsen. Effects of Teucrium polium spp. capitatum flavonoids on the lipid and carbohydrate metabolism in rats. Pharmaceutical biology. 2011 Sep; 49(9):885-92. doi: 10.3109/13880209.2011.552187. [PMID: 21619454]
  • Seed Niazmand, Maryam Esparham, Tahereh Hassannia, Mohammad Derakhshan. Cardiovascular effects of Teucrium polium L. extract in rabbit. Pharmacognosy magazine. 2011 Jul; 7(27):260-4. doi: 10.4103/0973-1296.84244. [PMID: 21969799]
  • Ahmad R Gohari, Soodabeh Saeidnia, Maryam Malmir, Abbass Hadjiakhoondi, Yousef Ajani. Flavones and rosmarinic acid from Salvia limbata. Natural product research. 2010 Dec; 24(20):1902-6. doi: 10.1080/14786411003766912. [PMID: 21108116]
  • Ai-Hua Zhao, Rong-Tao Li, Bei Jiang, Ji-Xia Zhang, Qin-Shi Zhao, Han-Dong Sun. Three new compounds from Isodon melissoides. Journal of Asian natural products research. 2005 Apr; 7(2):151-6. doi: 10.1080/1028602042000204108. [PMID: 15621618]
  • Sheng Lin, Qi-Wei Zhang, Ning-Ning Zhang, Yong-Xin Zhang. [Determination of flavonoids in buds of Herba Artemisiae Scopariae by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Apr; 30(8):591-4. doi: . [PMID: 16011282]
  • Tsuneatsu Nagao, Fumiko Abe, Junei Kinjo, Hikaru Okabe. Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship. Biological & pharmaceutical bulletin. 2002 Jul; 25(7):875-9. doi: 10.1248/bpb.25.875. [PMID: 12132661]
  • Qi-wei Zhang, Yong-xi Zhang, Ying Zhang, Yong-qing Xiao, Zhi-min Wang. [Studies on chemical constituents in buds of Artemisia scoparia]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2002 Mar; 27(3):202-4. doi: . [PMID: 12774401]
  • H Blomgren, G Kling-Andersson. Growth inhibition of human malignant glioma cells in vitro by agents which interfere with biosynthesis of eicosanoids. Anticancer research. 1992 May; 12(3):981-6. doi: NULL. [PMID: 1622156]