Veratramine (BioDeep_00000002577)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


3-PIPERIDINOL, 5-METHYL-2-((1S)-1-((3S,6AR,11AS,11BR)-2,3,4,6,6A,11,11A,11B-OCTAHYDRO-3-HYDROXY-10,11B-DIMETHYL-1H-BENZO(A)FLUOREN-9-YL)ETHYL)-, (2S,3R,5S)-

化学式: C27H39NO2 (409.2981)
中文名称: 黎芦胺, 黎芦碱, 藜芦铵
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 91.25%

分子结构信息

SMILES: Cc1c(C(C)C2NCC(C)CC2O)ccc2c1CC1C2CC=C2CC(O)CCC21C
InChI: InChI=1S/C27H39NO2/c1-15-11-25(30)26(28-14-15)17(3)20-7-8-21-22-6-5-18-12-19(29)9-10-27(18,4)24(22)13-23(21)16(20)2/h5,7-8,15,17,19,22,24-26,28-30H,6,9-14H2,1-4H3

描述信息

Veratramine is a piperidine alkaloid comprising the 14,15,16,17-tetradehydro derivative of veratraman having two hydroxy groups at the 3- and 23-positions. It derives from a hydride of a veratraman.
Veratramine is a natural product found in Veratrum grandiflorum, Veratrum mengtzeanum, and other organisms with data available.
Veratramine is a hypotensive alkaloid isolated from the rhizomes of Veratrum.
A piperidine alkaloid comprising the 14,15,16,17-tetradehydro derivative of veratraman having two hydroxy groups at the 3- and 23-positions.
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents > D014704 - Veratrum Alkaloids
Data obtained from a veratramine standard purchased from Logan Natural Products, Logan, Utah USA.
Veratramine(NSC17821; NSC23880) is useful as a signal transduction inhibitor for treating tumors.
Veratramine(NSC17821; NSC23880) is useful as a signal transduction inhibitor for treating tumors.

同义名列表

20 个代谢物同义名

3-PIPERIDINOL, 5-METHYL-2-((1S)-1-((3S,6AR,11AS,11BR)-2,3,4,6,6A,11,11A,11B-OCTAHYDRO-3-HYDROXY-10,11B-DIMETHYL-1H-BENZO(A)FLUOREN-9-YL)ETHYL)-, (2S,3R,5S)-; (2S,3R,5S)-2-((S)-1-((3S,6aR,11aS,11bR)-3-hydroxy-10,11b-dimethyl-2,3,4,6,6a,11,11a,11b-octahydro-1H-benzo[a]fluoren-9-yl)ethyl)-5-methylpiperidin-3-ol; (2S,3R,5S)-2-[(1S)-1-[(3S,6aR,11aS,11bR)-3-hydroxy-10,11b-dimethyl-1,2,3,4,6,6a,11,11a-octahydrobenzo[a]fluoren-9-yl]ethyl]-5-methyl-piperidin-3-ol; (2S,3R,5S)-2-[(1S)-1-[(3S,6aR,11aS,11bR)-3-hydroxy-10,11b-dimethyl-1,2,3,4,6,6a,11,11a-octahydrobenzo[a]fluoren-9-yl]ethyl]-5-methylpiperidin-3-ol; 5-methyl-2-(1-(2,3,4,6,6a,11,11a,11b-octahydro- 3-hydroxy-10,11b-dimethyl-1H-benzo(a)fluoren-9- yl)ethyl)piperidin-3-ol; Veratraman-3,23-diol, 14,15,16,17-tetradehydro-, (3-beta,23-beta)-; Veratraman-3,23-diol, 14,15,16,17-tetradehydro-, (3beta,23beta)-; Veratraman-3, 14,15,16,17-tetradehydro-, (3.beta.,23.beta.)-; (3beta,23beta)-14,15,16,17-Tetradehydroveratraman-3,23-diol; (3beta,23beta)-14,15,16,17-Teradehydroveratraman-3,23-diol; (3beta,23R)-14,15,16,17-tetradehydroveratraman-3,23-diol; WLN: L D6 B566 LU&TTTJ A1 E1 OQ FY1&- BT6MTJ CQ E1; 5-21-05-00297 (Beilstein Handbook Reference); 14,15,16,17-Tetradehydroveratraman-3,23-diol; VERATRAMINE [MI]; Veratramine; veratramin; NSC17821; NSC23880; Veratramine



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

57 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 11 CAT, COASY, CYP2D6, EDN1, MARK2, MDM2, MTOR, PIK3C3, PIK3CA, SMO, SULT2A1
Peripheral membrane protein 1 MTOR
Endoplasmic reticulum membrane 3 CYP2D6, MTOR, SIGMAR1
Cytoplasmic vesicle, autophagosome 1 PIK3C3
Nucleus 5 JUND, MDM2, MTOR, MYB, SMO
autophagosome 1 PIK3C3
cytosol 10 CAT, LIPE, MDM2, MTOR, MYB, PIK3C3, PIK3CA, SIGMAR1, SMO, SULT2A1
dendrite 3 MARK2, MTOR, SMO
phagocytic vesicle 1 MTOR
phosphatidylinositol 3-kinase complex, class III 1 PIK3C3
nucleoplasm 6 JUND, MARK2, MDM2, MTOR, MYB, SMO
RNA polymerase II transcription regulator complex 2 JUND, MYB
Cell membrane 3 LIPE, SIGMAR1, SMO
Cytoplasmic side 1 MTOR
lamellipodium 1 PIK3CA
Multi-pass membrane protein 1 SMO
Golgi apparatus membrane 1 MTOR
glutamatergic synapse 3 MDM2, PIK3C3, SIGMAR1
Golgi apparatus 1 SMO
Golgi membrane 2 INS, MTOR
growth cone 1 SIGMAR1
lysosomal membrane 2 EGF, MTOR
Cytoplasm, cytosol 1 LIPE
Lysosome 1 MTOR
endosome 1 PIK3C3
plasma membrane 6 BCHE, EGF, MARK2, MDM2, PIK3CA, SMO
Membrane 9 CAT, CYP2D6, EGF, LIPE, MARK2, MTOR, MYB, PIK3C3, SIGMAR1
axon 1 CCK
caveola 1 LIPE
extracellular exosome 4 CAT, COASY, EGF, SMO
Lysosome membrane 1 MTOR
endoplasmic reticulum 3 CYP2D6, SIGMAR1, SMO
extracellular space 5 BCHE, CCK, EDN1, EGF, INS
perinuclear region of cytoplasm 1 PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 4 CAT, COASY, CYP2D6, MARK2
protein-containing complex 2 CAT, MDM2
intracellular membrane-bounded organelle 3 CAT, CYP2D6, SMO
Microsome membrane 2 CYP2D6, MTOR
postsynaptic density 2 MDM2, SIGMAR1
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 4 BCHE, CCK, EDN1, INS
extracellular region 6 BCHE, CAT, CCK, EDN1, EGF, INS
Mitochondrion outer membrane 1 MTOR
Single-pass membrane protein 2 CYP2D6, SIGMAR1
mitochondrial outer membrane 2 COASY, MTOR
basal part of cell 1 EDN1
Mitochondrion matrix 1 COASY
mitochondrial matrix 2 CAT, COASY
anchoring junction 1 SIGMAR1
transcription regulator complex 1 JUND
Cell projection, cilium 1 SMO
ciliary membrane 1 SMO
nuclear membrane 1 SMO
cytoplasmic vesicle 1 SIGMAR1
nucleolus 1 MDM2
midbody 1 PIK3C3
focal adhesion 1 CAT
GABA-ergic synapse 1 PIK3C3
Peroxisome 2 CAT, PIK3C3
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 MTOR
PML body 1 MTOR
lateral plasma membrane 1 MARK2
axoneme 1 PIK3C3
ciliary tip 1 SMO
Nucleus inner membrane 1 SIGMAR1
Nucleus outer membrane 1 SIGMAR1
nuclear inner membrane 1 SIGMAR1
nuclear outer membrane 1 SIGMAR1
Late endosome 2 PIK3C3, SMO
cilium 1 SMO
chromatin 1 JUND
phagocytic vesicle membrane 1 PIK3C3
centriole 1 SMO
Nucleus, nucleolus 1 MDM2
actin filament 1 MARK2
blood microparticle 1 BCHE
nuclear envelope 2 MTOR, SIGMAR1
Nucleus envelope 1 SIGMAR1
Endomembrane system 1 MTOR
endosome lumen 1 INS
Lipid droplet 2 LIPE, SIGMAR1
Membrane, caveola 1 LIPE
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
Nucleus, nucleoplasm 1 MDM2
Cell projection, dendrite 1 MARK2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 BCHE, INS
nuclear matrix 1 MYB
transcription repressor complex 2 JUND, MDM2
platelet alpha granule lumen 1 EGF
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
endocytic vesicle membrane 2 MDM2, SMO
transport vesicle 2 EDN1, INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 1 SIGMAR1
presynaptic endosome 1 PIK3C3
nuclear envelope lumen 1 BCHE
9+0 non-motile cilium 1 SMO
clathrin-coated endocytic vesicle membrane 1 EGF
endoplasmic reticulum-Golgi intermediate compartment 1 SMO
Cytoplasmic vesicle, phagosome 1 MTOR
postsynaptic endosome 1 PIK3C3
transcription factor AP-1 complex 1 JUND
Autolysosome 1 PIK3C3
rough endoplasmic reticulum lumen 1 EDN1
catalase complex 1 CAT
Weibel-Palade body 1 EDN1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
microtubule bundle 1 MARK2


文献列表

  • Huan Chen, Pu Zhao, Caisheng Zhang, Xin Ming, Chaofeng Zhang, Yong-Sam Jung, Yingjuan Qian. Veratramine inhibits porcine epidemic diarrhea virus entry through macropinocytosis by suppressing PI3K/Akt pathway. Virus research. 2023 Nov; 339(?):199260. doi: 10.1016/j.virusres.2023.199260. [PMID: 37923169]
  • Song Wang, Jiali Cui, Gaoqiong Zhao, Hongbin Liu, Jingkun Wang. Pharmacokinetics of Veratramine and Jervine from Alcohol Extracts of Radix Veratri. Computational and mathematical methods in medicine. 2022; 2022(?):8289548. doi: 10.1155/2022/8289548. [PMID: 35785141]
  • Matthew W Turner, Meagan Rossi, Vannessa Campfield, John French, Ellie Hunt, Emily Wade, Owen M McDougal. Steroidal alkaloid variation in Veratrum californicum as determined by modern methods of analytical analysis. Fitoterapia. 2019 Sep; 137(?):104281. doi: 10.1016/j.fitote.2019.104281. [PMID: 31381957]
  • Chunming Lyu, Yufeng Zhang, Wenbin Zhou, Shen Zhang, Fang Kou, Hai Wei, Ning Zhang, Zhong Zuo. Gender-Dependent Pharmacokinetics of Veratramine in Rats: In Vivo and In Vitro Evidence. The AAPS journal. 2016 Mar; 18(2):432-44. doi: 10.1208/s12248-016-9870-9. [PMID: 26791530]
  • Yue Cong, Jinggong Guo, Zhi Tang, Shuhai Lin, Qingchun Zhang, Jing Li, Zongwei Cai. Metabolism Study of Veratramine Associated with Neurotoxicity by Using HPLC-MSn. Journal of chromatographic science. 2015 Aug; 53(7):1092-9. doi: 10.1093/chromsci/bmu171. [PMID: 25547283]
  • Chunming Lyu, Wenbin Zhou, Yufeng Zhang, Shen Zhang, Fang Kou, Hai Wei, Ning Zhang, Zhong Zuo. Identification and characterization of in vitro and in vivo metabolites of steroidal alkaloid veratramine. Biopharmaceutics & drug disposition. 2015 Jul; 36(5):308-24. doi: 10.1002/bdd.1942. [PMID: 25765359]
  • Jian-Liang Zhou, Gui-Zhong Xin, Zi-Qi Shi, Mei-Ting Ren, Lian-Wen Qi, Hui-Jun Li, Ping Li. Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Journal of chromatography. A. 2010 Nov; 1217(45):7109-22. doi: 10.1016/j.chroma.2010.09.019. [PMID: 20926090]
  • Jian Tang, Hui-Liang Li, Yun-Heng Shen, Hui-Zi Jin, Shi-Kai Yan, Xiao-Hua Liu, Hua-Wu Zeng, Run-Hui Liu, Ye-Xiong Tan, Wei-Dong Zhang. Antitumor and antiplatelet activity of alkaloids from veratrum dahuricum. Phytotherapy research : PTR. 2010 Jun; 24(6):821-6. doi: 10.1002/ptr.3022. [PMID: 20013819]
  • Lang Zhao, Zhiqiang Ou, Kan Wang, Hongzheng Fu. [Steroidal alkaloids of from Veratrum dahuricum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Dec; 34(23):3039-42. doi: . [PMID: 20222419]
  • Jian Tang, Hui-Liang Li, Yun-Heng Shen, Hui-Zi Jin, Shi-Kai Yan, Run-Hui Liu, Wei-Dong Zhang. Antitumor activity of extracts and compounds from the rhizomes of Veratrum dahuricum. Phytotherapy research : PTR. 2008 Aug; 22(8):1093-6. doi: 10.1002/ptr.2463. [PMID: 18570211]
  • Lishu Wang, Wei Li, Yonghong Liu. Hypotensive effect and toxicology of total alkaloids and veratramine from roots and rhizomes of Veratrum nigrum L. in spontaneously hypertensive rats. Die Pharmazie. 2008 Aug; 63(8):606-10. doi: . [PMID: 18771011]
  • Sheng Zhang, Jianxia Zhou, Qingyao Shou, Ying Peng, Zhengwu Shen. [Determination of jervine and veratramine in Veratrum plants using high performance liquid chromatography coupled with evaporative light scattering detection]. Se pu = Chinese journal of chromatography. 2008 Jan; 26(1):56-9. doi: . [PMID: 18438025]
  • Rui Ma, Anneli Ritala, Kirsi-Marja Oksman-Caldentey, Heiko Rischer. Development of in vitro techniques for the important medicinal plant Veratrum californicum. Planta medica. 2006 Oct; 72(12):1142-8. doi: 10.1055/s-2006-946697. [PMID: 17024590]
  • Hui-Jun Li, Yan Jiang, Ping Li, Wen-Cai Ye. Puqienine F, a novel veratramine alkaloid from the bulbs of Fritillaria puqiensis. Chemical & pharmaceutical bulletin. 2006 May; 54(5):722-4. doi: 10.1248/cpb.54.722. [PMID: 16651778]
  • Y Iwanaga, T Kimura, N Miyashita, K Morikawa, O Nagata, Z Itoh, Y Kondo. Characterization of acetylcholinesterase-inhibition by itopride. Japanese journal of pharmacology. 1994 Nov; 66(3):317-22. doi: 10.1254/jjp.66.317. [PMID: 7869618]