Berbine (BioDeep_00000005748)

   


代谢物信息卡片


(-)-Berbine

化学式: C17H17N (235.1361)
中文名称: 小檗碱
谱图信息: 最多检出来源 Viridiplantae(plant) 25%

分子结构信息

SMILES: c1ccc2c(c1)CC1c3ccccc3CCN1C2
InChI: InChI=1S/C17H17N/c1-2-7-15-12-18-10-9-13-5-3-4-8-16(13)17(18)11-14(15)6-1/h1-8,17H,9-12H2

描述信息

同义名列表

3 个代谢物同义名

Berbine; (-)-Berbine; (S)-Tetrahydroprotoberberine



数据库引用编号

13 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)

3 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 7 ABCB1, ADRA1A, CALR, GJA1, PCSK9, RAC1, SRARP
Peripheral membrane protein 3 ACHE, CYP1B1, GORASP1
Endosome membrane 1 LDLR
Endoplasmic reticulum membrane 6 CALR, CYP1B1, DRD1, GJA1, HMOX1, RAC1
Nucleus 9 ACHE, ADRA1A, CALR, DRD1, GABPA, GJA1, HMOX1, RAC1, SRARP
cytosol 6 ADRA1A, CALR, GJA1, HMOX1, MAT1A, RAC1
dendrite 2 DRD2, RAC1
trans-Golgi network 1 RAC1
nucleoplasm 4 ADRA1A, GABPA, GJA1, HMOX1
Cell membrane 10 ABCB1, ACHE, ADRA1A, DRD1, DRD2, GJA1, KCNH2, LDLR, RAC1, TNF
Lipid-anchor 1 RAC1
Cytoplasmic side 3 GORASP1, HMOX1, RAC1
lamellipodium 1 RAC1
ruffle membrane 1 RAC1
Multi-pass membrane protein 7 ABCB1, ABCC2, ADRA1A, DRD1, DRD2, GJA1, KCNH2
Golgi apparatus membrane 2 DRD2, GORASP1
Synapse 3 ACHE, DRD2, RAC1
cell cortex 1 RAC1
cell junction 1 GJA1
cell surface 8 ABCB1, ABCC2, ACHE, CALR, KCNH2, LDLR, PCSK9, TNF
glutamatergic synapse 4 CALR, DRD1, DRD2, RAC1
Golgi apparatus 5 ACHE, GJA1, GORASP1, LDLR, PCSK9
Golgi membrane 3 DRD2, GJA1, GORASP1
lysosomal membrane 1 PCSK9
neuromuscular junction 1 ACHE
neuronal cell body 1 TNF
postsynapse 2 CALR, RAC1
presynaptic membrane 2 DRD1, DRD2
smooth endoplasmic reticulum 1 CALR
Cytoplasm, cytosol 1 CALR
Lysosome 2 LDLR, PCSK9
acrosomal vesicle 2 CALR, DRD2
endosome 1 PCSK9
plasma membrane 13 ABCB1, ABCC2, ACHE, ADRA1A, BCHE, DRD1, DRD2, GJA1, KCNH2, LDLR, PCSK9, RAC1, TNF
synaptic vesicle membrane 1 DRD2
Membrane 9 ABCB1, ABCC2, ACHE, CALR, CYP1B1, HMOX1, KCNH2, LDLR, RAC1
apical plasma membrane 3 ABCB1, ABCC2, GJA1
axon 1 DRD2
basolateral plasma membrane 1 LDLR
caveola 1 ADRA1A
extracellular exosome 3 ABCB1, CALR, RAC1
endoplasmic reticulum 4 CALR, GJA1, HMOX1, PCSK9
extracellular space 6 ACHE, BCHE, CALR, HMOX1, PCSK9, TNF
perinuclear region of cytoplasm 5 ACHE, CALR, HMOX1, KCNH2, PCSK9
gap junction 1 GJA1
intercalated disc 1 GJA1
intercellular canaliculus 1 ABCC2
mitochondrion 2 CYP1B1, GJA1
intracellular membrane-bounded organelle 3 ADRA1A, CYP1B1, GJA1
Microsome membrane 1 CYP1B1
Single-pass type I membrane protein 1 LDLR
Secreted 4 ACHE, BCHE, PCSK9, RAC1
extracellular region 6 ACHE, BCHE, CALR, PCSK9, RAC1, TNF
Single-pass membrane protein 1 LDLR
mitochondrial outer membrane 1 HMOX1
Extracellular side 1 ACHE
ciliary membrane 2 DRD1, DRD2
Nucleus membrane 1 ADRA1A
nuclear membrane 1 ADRA1A
external side of plasma membrane 3 CALR, LDLR, TNF
Secreted, extracellular space, extracellular matrix 1 CALR
low-density lipoprotein particle 1 LDLR
dendritic spine 3 DRD1, DRD2, RAC1
perikaryon 1 DRD2
cytoplasmic vesicle 1 RAC1
Early endosome 2 LDLR, PCSK9
Membrane, clathrin-coated pit 1 LDLR
apical part of cell 1 LDLR
clathrin-coated pit 1 LDLR
COPII-coated ER to Golgi transport vesicle 1 PCSK9
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 2 DRD1, DRD2
Apical cell membrane 2 ABCB1, ABCC2
Cell projection, lamellipodium 1 RAC1
Membrane raft 2 GJA1, TNF
focal adhesion 3 CALR, GJA1, RAC1
GABA-ergic synapse 2 DRD1, DRD2
cis-Golgi network 1 GORASP1
basement membrane 1 ACHE
Cell projection, dendritic spine 1 DRD1
collagen-containing extracellular matrix 1 CALR
Cell junction, gap junction 1 GJA1
connexin complex 1 GJA1
contractile muscle fiber 1 GJA1
fascia adherens 1 GJA1
intermediate filament 1 GJA1
lateral plasma membrane 2 DRD2, GJA1
Late endosome 2 LDLR, PCSK9
receptor complex 1 LDLR
cilium 2 DRD1, DRD2
chromatin 1 GABPA
phagocytic cup 1 TNF
phagocytic vesicle membrane 1 CALR
cytoskeleton 1 RAC1
cytoplasmic ribonucleoprotein granule 1 RAC1
blood microparticle 1 BCHE
non-motile cilium 2 DRD1, DRD2
Lipid-anchor, GPI-anchor 1 ACHE
sperm flagellum 1 DRD2
nuclear envelope 1 CALR
Recycling endosome membrane 1 RAC1
Endomembrane system 1 LDLR
sorting endosome 1 LDLR
Membrane, caveola 1 ADRA1A
monoatomic ion channel complex 1 KCNH2
Cell projection, dendrite 2 DRD1, RAC1
Melanosome 1 RAC1
Golgi-associated vesicle membrane 1 GJA1
side of membrane 1 ACHE
inward rectifier potassium channel complex 1 KCNH2
voltage-gated potassium channel complex 1 KCNH2
endoplasmic reticulum quality control compartment 1 CALR
secretory granule membrane 1 RAC1
endoplasmic reticulum lumen 3 BCHE, CALR, PCSK9
axon terminus 1 DRD2
endocytic vesicle 1 DRD2
tight junction 1 GJA1
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 CALR, GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
nuclear envelope lumen 1 BCHE
clathrin-coated endocytic vesicle membrane 1 LDLR
Sarcoplasmic reticulum lumen 1 CALR
synaptic cleft 1 ACHE
ficolin-1-rich granule membrane 1 RAC1
external side of apical plasma membrane 1 ABCB1
endolysosome membrane 2 LDLR, PCSK9
lumenal side of endoplasmic reticulum membrane 1 CALR
MHC class I peptide loading complex 1 CALR
dopaminergic synapse 1 DRD2
somatodendritic compartment 1 LDLR
extrinsic component of external side of plasma membrane 1 PCSK9
Cell projection, cilium membrane 1 DRD1
cell-cell contact zone 1 GJA1
endocytic vesicle lumen 1 CALR
ribosome 1 CALR
PCSK9-LDLR complex 2 LDLR, PCSK9
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
NADPH oxidase complex 1 RAC1
PCSK9-AnxA2 complex 1 PCSK9
Cytoplasmic vesicle, secretory vesicle, Cortical granule 1 CALR
cortical granule 1 CALR
Cytolytic granule 1 CALR
G protein-coupled receptor complex 2 DRD1, DRD2
[Isoform H]: Cell membrane 1 ACHE
methionine adenosyltransferase complex 1 MAT1A
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Wanli Zhao, Manyu Liu, Kemeng Liu, Hanqing Liu, Xiufeng Liu, Jihua Liu. An Enzymatic Strategy for the Selective Methylation of High-Value-Added Tetrahydroprotoberberine Alkaloids. International journal of molecular sciences. 2023 Oct; 24(20):. doi: 10.3390/ijms242015214. [PMID: 37894895]
  • Haixia Ge, Weitao Zhang, Kai Yuan, Hanyue Xue, Hao Cheng, Weijiao Chen, Yishi Xie, Jian Zhang, Xiaojun Xu, Peng Yang. Design, synthesis, and biological evaluation of novel tetrahydroprotoberberine derivatives to reduce SREBPs expression for the treatment of hyperlipidemia. European journal of medicinal chemistry. 2021 Oct; 221(?):113522. doi: 10.1016/j.ejmech.2021.113522. [PMID: 33984804]
  • Ling-Xian Liu, Liang Cao, Dan-Feng Shi, Zhen-Zhong Wang, Wei Xiao, Xin-Sheng Yao, Hai-Bo Li, Yang Yu. Metabolic profiles of Jin-hong tablets in rats by ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry. Biomedical chromatography : BMC. 2021 Jun; 35(6):e5072. doi: 10.1002/bmc.5072. [PMID: 33453065]
  • Dean E Lang, Jeremy S Morris, Michael Rowley, Miguel A Torres, Vook A Maksimovich, Peter J Facchini, Kenneth K S Ng. Structure-function studies of tetrahydroprotoberberine N-methyltransferase reveal the molecular basis of stereoselective substrate recognition. The Journal of biological chemistry. 2019 10; 294(40):14482-14498. doi: 10.1074/jbc.ra119.009214. [PMID: 31395658]
  • Da-Hong Li, Jian-Yong Li, Chun-Mei Xue, Tong Han, Chun-Mei Sai, Kai-Bo Wang, Jin-Cai Lu, Yong-Kui Jing, Hui-Ming Hua, Zhan-Lin Li. Antiproliferative Dimeric Aporphinoid Alkaloids from the Roots of Thalictrum cultratum. Journal of natural products. 2017 11; 80(11):2893-2904. doi: 10.1021/acs.jnatprod.7b00387. [PMID: 29131616]
  • Phuong Mai Le, Vandana Srivastava, Thanh Tam Nguyen, Bruno Pradines, Marylin Madamet, Joel Mosnier, Thi Thuy Trinh, Hoyun Lee. Stephanine from Stephania venosa (Blume) Spreng Showed Effective Antiplasmodial and Anticancer Activities, the Latter by Inducing Apoptosis through the Reverse of Mitotic Exit. Phytotherapy research : PTR. 2017 Sep; 31(9):1357-1368. doi: 10.1002/ptr.5861. [PMID: 28703314]
  • Jiayong He, Ying Liu, Yun Kang, Ping Yang, Yaqin Wang, Jixian Guo, Jianming Huang. Identification of Alkaloids in Stephania hainanensis by Liquid Chromatography Coupled with Quadrupole Time-of-flight Mass Spectrometry. Phytochemical analysis : PCA. 2016 May; 27(3-4):206-16. doi: 10.1002/pca.2618. [PMID: 27313158]
  • Daniel R Callejon, Thalita B Riul, Luis G P Feitosa, Thais Guaratini, Denise B Silva, Achyut Adhikari, Ram L S Shrestha, Lucas M M Marques, Marcelo D Baruffi, João L C Lopes, Norberto P Lopes. Leishmanicidal evaluation of tetrahydroprotoberberine and spirocyclic erythrina-alkaloids. Molecules (Basel, Switzerland). 2014 May; 19(5):5692-703. doi: 10.3390/molecules19055692. [PMID: 24802983]
  • Qiaoxia Liu, Shiyi Qiu, Hui Yu, Yanxiong Ke, Yu Jin, Xinmiao Liang. Selective separation of structure-related alkaloids in Rhizoma coptidis with "click" binaphthyl stationary phase and their structural elucidation with liquid chromatography-mass spectrometry. The Analyst. 2011 Oct; 136(20):4357-65. doi: 10.1039/c1an15444c. [PMID: 21881639]
  • Yiannis C Fiamegos, Panagiotis L Kastritis, Vassiliki Exarchou, Haley Han, Alexandre M J J Bonvin, Jacques Vervoort, Kim Lewis, Michael R Hamblin, George P Tegos. Antimicrobial and efflux pump inhibitory activity of caffeoylquinic acids from Artemisia absinthium against gram-positive pathogenic bacteria. PloS one. 2011 Apr; 6(4):e18127. doi: 10.1371/journal.pone.0018127. [PMID: 21483731]
  • Manoj K Pandey, Bokyung Sung, Ajaikumar B Kunnumakkara, Gautam Sethi, Madan M Chaturvedi, Bharat B Aggarwal. Berberine modifies cysteine 179 of IkappaBalpha kinase, suppresses nuclear factor-kappaB-regulated antiapoptotic gene products, and potentiates apoptosis. Cancer research. 2008 Jul; 68(13):5370-9. doi: 10.1158/0008-5472.can-08-0511. [PMID: 18593939]
  • E K Marinova, D B Nikolova, D N Popova, G B Gallacher, N D Ivanovska. Suppression of experimental autoimmune tubulointerstitial nephritis in BALB/c mice by berberine. Immunopharmacology. 2000 Jun; 48(1):9-16. doi: 10.1016/s0162-3109(99)00189-7. [PMID: 10822084]
  • X L Jin, Y Shao, M J Wang, L J Chen, G Z Jin. Tetrahydroprotoberberines inhibit lipid peroxidation and scavenge hydroxyl free radicals. Acta pharmacologica Sinica. 2000 May; 21(5):477-80. doi: ". [PMID: 11324451]