febrifugine (BioDeep_00000000490)

 

Secondary id: BioDeep_00000229911

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


3-[[(3aS,7aS)-2-hydroxy-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridin-2-yl]methyl]quinazolin-4-one

化学式: C16H19N3O3 (301.1426)
中文名称: 常山乙素, (+)-异常山碱, 异常山碱, 异常山乙素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 77.99%

分子结构信息

SMILES: C1CC(C(NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
InChI: InChI=1S/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2

描述信息

Isofebrifugine is a member of quinazolines.
Isofebrifugine is a natural product found in Hydrangea febrifuga and Hydrangea macrophylla with data available.
Febrifugine is a quinazolinone alkaloid found in the roots and leaves of Dichroa febrifuga, with antimalarial activity [1].
Febrifugine is a quinazolinone alkaloid found in the roots and leaves of Dichroa febrifuga, with antimalarial activity [1].

同义名列表

12 个代谢物同义名

beta-Dichroine; febrifugine; alpha-Dichroine; Dichroine-alpha; isofebrifugine; 3-(3-(3-Hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3H)-one; 3-[[(3aS,7aS)-2-hydroxy-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridin-2-yl]methyl]quinazolin-4-one; 3-[(3aS,7aS)-2-Hydroxyperhydrofuro[3,2-b]pyridin-2-ylmethyl]-3,4-dihydroquinazolin-4-one; 3-[(2-hydroxy-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridin-2-yl)methyl]quinazolin-4-one; 3-[(2-Hydroxyoctahydrofuro[3,2-b]pyridin-2-yl)methyl]quinazolin-4(3H)-one; Isofebrifugine; Febrifugine



数据库引用编号

36 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)

21 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 12 AARS1, BCL2, CCND1, CTNNB1, HDAC2, HIF1A, MYC, PLK1, RPS6KB1, SMAD3, TGFB1, UTRN
Peripheral membrane protein 1 UTRN
Endoplasmic reticulum membrane 1 BCL2
Nucleus 12 AARS1, BCL2, CCND1, CTNNB1, GABPA, HDAC2, HIF1A, MYC, PLK1, RPS6KB1, SMAD3, TGFB1
cytosol 8 AARS1, BCL2, CCND1, CTNNB1, HIF1A, PLK1, RPS6KB1, SMAD3
nuclear body 1 HIF1A
centrosome 3 CCND1, CTNNB1, PLK1
nucleoplasm 10 CCND1, CTNNB1, GABPA, HDAC2, HIF1A, MYC, PLK1, RPS6KB1, SMAD3, UTRN
RNA polymerase II transcription regulator complex 1 HIF1A
Cell membrane 3 CTNNB1, TNF, UTRN
Cytoplasmic side 1 UTRN
lamellipodium 1 CTNNB1
Synapse 2 CTNNB1, UTRN
cell cortex 2 CTNNB1, PDZD4
cell junction 1 CTNNB1
cell surface 3 RPS6KB1, TGFB1, TNF
glutamatergic synapse 2 CTNNB1, RPS6KB1
neuromuscular junction 1 UTRN
neuronal cell body 2 TGFB1, TNF
postsynapse 1 RPS6KB1
presynaptic membrane 1 CTNNB1
sarcolemma 1 UTRN
plasma membrane 5 CTNNB1, SMAD3, TGFB1, TNF, UTRN
Membrane 6 AARS1, BCL2, CTNNB1, HDAC2, MYC, UTRN
axon 2 CCK, TGFB1
basolateral plasma membrane 1 CTNNB1
extracellular exosome 3 AARS1, CTNNB1, UTRN
endoplasmic reticulum 1 BCL2
extracellular space 6 CCK, IL17A, IL4, IL6, TGFB1, TNF
perinuclear region of cytoplasm 2 CTNNB1, RPS6KB1
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 2 CCND1, CTNNB1
mitochondrion 3 AARS1, BCL2, RPS6KB1
protein-containing complex 6 BCL2, CTNNB1, HDAC2, HIF1A, MYC, UTRN
filopodium 1 UTRN
ESC/E(Z) complex 1 HDAC2
Secreted 5 CCK, IL17A, IL4, IL6, TGFB1
extracellular region 7 CCK, GZMK, IL17A, IL4, IL6, TGFB1, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, RPS6KB1
transcription regulator complex 2 CTNNB1, SMAD3
centriolar satellite 1 PLK1
motile cilium 1 HIF1A
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 PLK1
Nucleus membrane 2 BCL2, CCND1
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, CCND1
external side of plasma membrane 2 IL17A, TNF
Secreted, extracellular space, extracellular matrix 1 TGFB1
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
microtubule cytoskeleton 1 PLK1
nucleolus 1 MYC
Wnt signalosome 1 CTNNB1
axon cytoplasm 1 HIF1A
midbody 1 PLK1
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
recycling endosome 1 TNF
spindle midzone 1 PLK1
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 2 CTNNB1, UTRN
Membrane raft 1 TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 CTNNB1
Cytoplasm, cytoskeleton, spindle 1 PLK1
focal adhesion 1 CTNNB1
spindle 1 PLK1
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
extracellular matrix 1 TGFB1
collagen-containing extracellular matrix 1 TGFB1
secretory granule 2 GZMK, TGFB1
fascia adherens 1 CTNNB1
lateral plasma membrane 1 CTNNB1
nuclear speck 1 HIF1A
Nucleus outer membrane 1 UTRN
nuclear inner membrane 1 SMAD3
nuclear outer membrane 1 UTRN
receptor complex 1 SMAD3
neuron projection 1 RPS6KB1
chromatin 6 GABPA, HDAC2, HIF1A, MYC, PLK1, SMAD3
phagocytic cup 1 TNF
cell periphery 1 CTNNB1
cytoskeleton 1 UTRN
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
centriole 1 PLK1
Nucleus, nucleolus 1 MYC
spindle pole 2 CTNNB1, PLK1
chromosome, telomeric region 1 HDAC2
Cytoplasm, cell cortex 1 PDZD4
blood microparticle 1 TGFB1
postsynaptic density, intracellular component 1 CTNNB1
microvillus membrane 1 CTNNB1
nuclear envelope 1 MYC
Endomembrane system 1 CTNNB1
Nucleus, nucleoplasm 1 MYC
Nucleus speckle 1 HIF1A
euchromatin 2 CTNNB1, HIF1A
myelin sheath 1 BCL2
filopodium membrane 1 UTRN
Golgi lumen 1 TGFB1
endoplasmic reticulum lumen 1 IL6
transcription repressor complex 1 CCND1
platelet alpha granule lumen 1 TGFB1
kinetochore 1 PLK1
histone deacetylase complex 1 HDAC2
mitotic spindle pole 1 PLK1
RNA polymerase II transcription repressor complex 1 MYC
beta-catenin-TCF complex 1 CTNNB1
NuRD complex 1 HDAC2
Single-pass type IV membrane protein 1 UTRN
outer kinetochore 1 PLK1
presynaptic active zone cytoplasmic component 1 CTNNB1
heteromeric SMAD protein complex 1 SMAD3
Synapse, synaptosome 1 RPS6KB1
SMAD protein complex 1 SMAD3
Sin3-type complex 1 HDAC2
protein-DNA complex 1 CTNNB1
synaptonemal complex 1 PLK1
dystrophin-associated glycoprotein complex 1 UTRN
Rough endoplasmic reticulum 1 MYC
catenin complex 1 CTNNB1
cyclin-dependent protein kinase holoenzyme complex 1 CCND1
Myc-Max complex 1 MYC
[Latency-associated peptide]: Secreted, extracellular space, extracellular matrix 1 TGFB1
[Transforming growth factor beta-1]: Secreted 1 TGFB1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
BAD-BCL-2 complex 1 BCL2
cyclin D1-CDK4 complex 1 CCND1
beta-catenin-TCF7L2 complex 1 CTNNB1
cyclin D1-CDK6 complex 1 CCND1
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
nucleoplasmic reticulum 1 MYC


文献列表

  • Jingyuan Chen, Shuhao Fan, Jianhua Guo, Jian Yang, Le Pan, Yong Xia. Discovery of anticancer function of Febrifugine: Inhibition of cell proliferation, induction of apoptosis and suppression steroid synthesis in bladder cancer cells. Toxicology and applied pharmacology. 2024 Mar; 484(?):116878. doi: 10.1016/j.taap.2024.116878. [PMID: 38431229]
  • Ping Ping Li, Lei Zhang, Jian Ping Wang. Research Note: Study on the residue depletion of febrifugine and isofebrifugine in broiler chicken. Poultry science. 2021 Oct; 100(10):101390. doi: 10.1016/j.psj.2021.101390. [PMID: 34391965]
  • Liu-Qing Sheng, Jia-Lei Ma. Preparative separation of two isomeric antimalaria alkaloids febrifugine and isofebrifugine from Dichroa febrifuga roots by countercurrent chromatography. Journal of separation science. 2021 May; 44(10):2153-2159. doi: 10.1002/jssc.202001257. [PMID: 33811736]
  • Ji-Yuan Zhang, Xiao-Rui Fan, Xiao-Qian Liu, Xiao-Wei Yu, Li-Xin Yang, Zhi-Ting Guo, Wei-Hong Feng, Zhi-Min Wang, Chun Li. [Quantitative determination of febrifugine by proton nuclear magnetic resonance spectroscopy with internal standard method]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2018 Jan; 43(1):134-138. doi: 10.19540/j.cnki.cjcmm.20171027.005. [PMID: 29552823]
  • Ji-Yuan Zhang, Xiao-Qian Liu, Li-Xin Yang, Wei-Hong Feng, Zhi-Min Wang, Chun Li. [Investigation on stability and degradation kinetics of febrifugine]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 Aug; 42(16):3178-3184. doi: 10.19540/j.cnki.cjcmm.2017.0126. [PMID: 29171238]
  • Ji-Yuan Zhang, Zi-Han Liu, Xiao-Qian Liu, Wei-Hong Feng, Li-Xin Yang, Zhi-Min Wang, Chun Li. [Simultaneous determination of febrifugine and isofebrifugine in Dichroa febrifuga root by HPLC method]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 May; 42(9):1711-1716. doi: 10.19540/j.cnki.cjcmm.20170224.017. [PMID: 29082694]
  • Jonathan D Herman, Lauren R Pepper, Joseph F Cortese, Guillermina Estiu, Kevin Galinsky, Vanessa Zuzarte-Luis, Emily R Derbyshire, Ulf Ribacke, Amanda K Lukens, Sofia A Santos, Vishal Patel, Clary B Clish, William J Sullivan, Huihao Zhou, Selina E Bopp, Paul Schimmel, Susan Lindquist, Jon Clardy, Maria M Mota, Tracy L Keller, Malcolm Whitman, Olaf Wiest, Dyann F Wirth, Ralph Mazitschek. The cytoplasmic prolyl-tRNA synthetase of the malaria parasite is a dual-stage target of febrifugine and its analogs. Science translational medicine. 2015 May; 7(288):288ra77. doi: 10.1126/scitranslmed.aaa3575. [PMID: 25995223]
  • Huihao Zhou, Litao Sun, Xiang-Lei Yang, Paul Schimmel. ATP-directed capture of bioactive herbal-based medicine on human tRNA synthetase. Nature. 2013 Feb; 494(7435):121-4. doi: 10.1038/nature11774. [PMID: 23263184]
  • Tracy L Keller, Davide Zocco, Mark S Sundrud, Margaret Hendrick, Maja Edenius, Jinah Yum, Yeon-Jin Kim, Hak-Kyo Lee, Joseph F Cortese, Dyann F Wirth, John David Dignam, Anjana Rao, Chang-Yeol Yeo, Ralph Mazitschek, Malcolm Whitman. Halofuginone and other febrifugine derivatives inhibit prolyl-tRNA synthetase. Nature chemical biology. 2012 Feb; 8(3):311-7. doi: 10.1038/nchembio.790. [PMID: 22327401]
  • Timothy N C Wells. Natural products as starting points for future anti-malarial therapies: going back to our roots?. Malaria journal. 2011 Mar; 10 Suppl 1(?):S3. doi: 10.1186/1475-2875-10-s1-s3. [PMID: 21411014]
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