Anagyrine (BioDeep_00000000654)

 

Secondary id: BioDeep_00000016677

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


7,14-Methano-4H,6H-dipyrido(1,2-a:1,2-e)(1,5)diazocin-4-one, 7,7a,8,9,10,11,13,14-octahydro-, (7R-(7alpha,7aalpha,14alpha))-

化学式: C15H20N2O (244.1576)
中文名称: 安纳基林, 黄华碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 87.84%

分子结构信息

SMILES: C1CCN2CC3CC(C2C1)CN4C3=CC=CC4=O
InChI: InChI=1S/C15H20N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h3,5-6,11-13H,1-2,4,7-10H2

描述信息

Anagyrine is an alkaloid.
Anagyrine is a natural product found in Daphniphyllum oldhamii, Ormosia fordiana, and other organisms with data available.
Thermospine is a natural product found in Platycelyphium voense, Thermopsis mongolica, and other organisms with data available.
Thermopsine is a quinolizidine alkaloid isolated from the fruits and pods and stem bark of Sophora velutina subsp. Thermopsine has antibacterial activity[1].

同义名列表

21 个代谢物同义名

7,7a,8,9,10,11,13,14-octahydro-7,14-memethano-4H,6H-dipyrido(1,2-a:1,2-e)(1,5)diazocin-4-one; (1S,9R,10R)-7,15-diazatetracyclo[7.7.1.0?,?.0??,??]heptadeca-2,4-dien-6-one; (1S,9R,10R)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2,4-dien-6-one; 3,4,5,6-Tetradehydrospartein-2-one; FQEQMASDZFXSJI-WXRRBKDZSA-N; Camoensidine; ANAGYRINE; 7,14-Methano-4H,6H-dipyrido(1,2-a:1,2-e)(1,5)diazocin-4-one, 7,7a,8,9,10,11,13,14-octahydro-, (7R-(7alpha,7aalpha,14alpha))-; 7,6H-dipyrido[1,2-a:1,2-e][1,5]diazocin-4-one, 7,7a,8,9,10,11,13,14-octahydro-, [7R-(7.alpha.,7a.alpha.,14.alpha.)]-; (7R,14R,14aS)-1,3,4,6,7,13,14,14a-octahydro-2H,11H-7,14-methanodipyrido[1,2-a:1,2-e][1,5]diazocin-11-one; (7R,7aS,14R)-7,7a,8,9,10,11,13,14-Octahydro-7,14-methanodipyrido[1,2-a:1,2-e][1,5]diazocin-4(6H)-one; (1R,9R,10S)-7,15-diazatetracyclo[7.7.1.0?,?.0??,??]heptadeca-2,4-dien-6-one; (1R,9R,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2,4-dien-6-one; 1,2-Benzenediol, 4-ethynyl-; (-)-Thermopsine; THERMOPSINE,1-; l-Thermopsine; Thermopsine; Thermospine; Thermospine; Anagyrine



数据库引用编号

33 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)

518 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 AKAP13, AKT1, ANXA5, BCL2, CASP3, CYP3A4, EGFR, MMP3, PIK3C2A, PTGS2, STAT3, TP53
Peripheral membrane protein 4 ACHE, AKAP13, ANXA5, PTGS2
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 4 BCL2, CYP3A4, EGFR, PTGS2
Nucleus 11 ACHE, AKAP13, AKT1, BCL2, CASP3, EGFR, MMP3, PARP1, PIK3C2A, STAT3, TP53
cytosol 10 AKAP13, AKT1, ANXA5, BCL2, CASP3, MMP3, PARP1, PIK3C2A, STAT3, TP53
nuclear body 1 PARP1
trans-Golgi network 1 PIK3C2A
centrosome 1 TP53
nucleoplasm 6 AKT1, CASP3, PARP1, PIK3C2A, STAT3, TP53
RNA polymerase II transcription regulator complex 1 STAT3
Cell membrane 4 ACHE, AKT1, EGFR, PIK3C2A
lamellipodium 1 AKT1
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Synapse 1 ACHE
cell cortex 2 AKAP13, AKT1
cell junction 1 EGFR
cell surface 2 ACHE, EGFR
glutamatergic synapse 3 AKT1, CASP3, EGFR
Golgi apparatus 1 ACHE
Golgi membrane 1 EGFR
neuromuscular junction 1 ACHE
neuronal cell body 1 CASP3
postsynapse 1 AKT1
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 AKAP13, PARP1
endosome 1 EGFR
plasma membrane 5 ACHE, AKT1, EGFR, PIK3C2A, STAT3
Membrane 10 ACHE, AKAP13, AKT1, ANXA5, BCL2, CYP3A4, EGFR, PARP1, PIK3C2A, TP53
apical plasma membrane 1 EGFR
basolateral plasma membrane 1 EGFR
caveola 1 PTGS2
extracellular exosome 3 ANXA5, MMP9, PIK3C2A
endoplasmic reticulum 3 BCL2, PTGS2, TP53
extracellular space 6 ACHE, EGFR, IL4, MMP1, MMP3, MMP9
perinuclear region of cytoplasm 2 ACHE, EGFR
mitochondrion 4 BCL2, MMP3, PARP1, TP53
protein-containing complex 6 AKT1, BCL2, EGFR, PARP1, PTGS2, TP53
intracellular membrane-bounded organelle 2 CYP3A4, PIK3C2A
Microsome membrane 2 CYP3A4, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 EGFR
Secreted 3 ACHE, IL4, MMP3
extracellular region 6 ACHE, ANXA5, IL4, MMP1, MMP3, MMP9
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Mitochondrion matrix 1 TP53
mitochondrial matrix 1 TP53
Extracellular side 1 ACHE
transcription regulator complex 3 PARP1, STAT3, TP53
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, EGFR
external side of plasma membrane 1 ANXA5
Secreted, extracellular space, extracellular matrix 2 MMP1, MMP9
microtubule cytoskeleton 1 AKT1
nucleolus 2 PARP1, TP53
cell-cell junction 1 AKT1
vesicle 2 AKT1, PIK3C2A
Membrane raft 1 EGFR
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 TP53
focal adhesion 2 ANXA5, EGFR
spindle 1 AKT1
extracellular matrix 2 MMP1, MMP3
basement membrane 1 ACHE
intracellular vesicle 1 EGFR
Nucleus, PML body 1 TP53
PML body 1 TP53
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 2 ANXA5, MMP9
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 EGFR
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
ciliary basal body 1 AKT1
chromatin 3 PARP1, STAT3, TP53
Chromosome 1 PARP1
Golgi apparatus, trans-Golgi network 1 PIK3C2A
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
Cytoplasm, cell cortex 1 AKAP13
Lipid-anchor, GPI-anchor 1 ACHE
site of double-strand break 2 PARP1, TP53
nuclear envelope 1 PARP1
side of membrane 1 ACHE
germ cell nucleus 1 TP53
replication fork 1 TP53
myelin sheath 1 BCL2
basal plasma membrane 1 EGFR
clathrin-coated vesicle 1 PIK3C2A
synaptic membrane 1 EGFR
ficolin-1-rich granule lumen 1 MMP9
endoplasmic reticulum lumen 1 PTGS2
nuclear matrix 1 TP53
transcription repressor complex 1 TP53
phosphatidylinositol 3-kinase complex 1 PIK3C2A
tertiary granule lumen 1 MMP9
Cytoplasmic vesicle, clathrin-coated vesicle 1 PIK3C2A
vesicle membrane 1 ANXA5
clathrin-coated endocytic vesicle membrane 1 EGFR
[Isoform 1]: Nucleus 1 TP53
synaptic cleft 1 ACHE
protein-DNA complex 1 PARP1
death-inducing signaling complex 1 CASP3
site of DNA damage 1 PARP1
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
endothelial microparticle 1 ANXA5
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
BAD-BCL-2 complex 1 BCL2
[Isoform H]: Cell membrane 1 ACHE


文献列表

  • Li-Jun He, Jun-Shan Liu, Ding Luo, Yuan-Ru Zheng, Yu-Bo Zhang, Guo-Cai Wang, Yao-Lan Li. Quinolizidine alkaloids from Sophora tonkinensis and their anti-inflammatory activities. Fitoterapia. 2019 Nov; 139(?):104391. doi: 10.1016/j.fitote.2019.104391. [PMID: 31682871]
  • Benedict T Green, Stephen T Lee, Kevin D Welch, Daniel Cook. Anagyrine desensitization of peripheral nicotinic acetylcholine receptors. A potential biomarker of quinolizidine alkaloid teratogenesis in cattle. Research in veterinary science. 2017 Dec; 115(?):195-200. doi: 10.1016/j.rvsc.2017.04.019. [PMID: 28494312]
  • Jeanne I Rader, Rahul S Pawar. Primary constituents of blue cohosh: quantification in dietary supplements and potential for toxicity. Analytical and bioanalytical chemistry. 2013 May; 405(13):4409-17. doi: 10.1007/s00216-013-6783-7. [PMID: 23420136]
  • N Merghoub, L Benbacer, H El Btaouri, H Ait Benhassou, C Terryn, M Attaleb, C Madoulet, A Benjouad, M El Mzibri, H Morjani, S Amzazi. In vitro antiproliferative effect and induction of apoptosis by Retama monosperma L. extract in human cervical cancer cells. Cellular and molecular biology (Noisy-le-Grand, France). 2011 Oct; 57 Suppl(?):OL1581-91. doi: 10.5772/30025. [PMID: 22000488]
  • Benedict T Green, Stephen T Lee, Kip E Panter, Kevin D Welch, Daniel Cook, James A Pfister, William R Kem. Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors. Neurotoxicology and teratology. 2010 May; 32(3):383-90. doi: 10.1016/j.ntt.2010.01.011. [PMID: 20116429]
  • S T Lee, K E Panter, J A Pfister, D R Gardner, K D Welch. The effect of body condition on serum concentrations of two teratogenic alkaloids (anagyrine and ammodendrine) from lupines (Lupinus species) that cause crooked calf disease. Journal of animal science. 2008 Oct; 86(10):2771-8. doi: 10.2527/jas.2007-0610. [PMID: 18539842]
  • Dolores Pérez-Laínez, Rosario García-Mateos, Ruben San Miguel-Chávez, Marcos Soto-Hernández, Enrique Rodríguez-Pérez, Geofrey Kite. Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Sep; 63(9-10):653-7. doi: 10.1515/znc-2008-9-1007. [PMID: 19040102]
  • Stephen T Lee, Daniel Cook, Kip E Panter, Dale R Gardner, Michael H Ralphs, Ernie S Motteram, James A Pfister, Clive C Gay. Lupine induced "crooked calf disease" in Washington and Oregon: identification of the alkaloid profiles in Lupinus sulfureus, Lupinus leucophyllus, and Lupinus sericeus. Journal of agricultural and food chemistry. 2007 Dec; 55(26):10649-55. doi: 10.1021/jf0723110. [PMID: 18038992]
  • Stephen T Lee, Michael H Ralphs, Kip E Panter, Daniel Cook, Dale R Gardner. Alkaloid profiles, concentration, and pools in velvet lupine (Lupinus leucophyllus) over the growing season. Journal of chemical ecology. 2007 Jan; 33(1):75-84. doi: 10.1007/s10886-006-9211-z. [PMID: 17146716]
  • G Innocenti, S Dall'Acqua, G Viola, M C Loi. Cytotoxic constituents from Anagyris foetida leaves. Fitoterapia. 2006 Dec; 77(7-8):595-7. doi: 10.1016/j.fitote.2006.06.012. [PMID: 16887297]
  • Alice Martins, Michael Wink, Andreas Tei, Michèle Brum-Bousquet, François Tillequin, Amélia-Pilar Rauter. A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry. Phytochemical analysis : PCA. 2005 Jul; 16(4):264-6. doi: 10.1002/pca.832. [PMID: 16042152]
  • Clive C Gay, Kip E Panter, Katrina L Mealey, John M Gay, Steven W Hjartarson, Ahmed Tibary, Ernie S Motteram, Terrie Wierenga, Lynn F James. Comparison of plasma disposition of alkaloids after lupine challenge in cattle that had given birth to calves with lupine-induced arthrogryposis or clinically normal calves. American journal of veterinary research. 2004 Nov; 65(11):1580-3. doi: 10.2460/ajvr.2004.65.1580. [PMID: 15566098]
  • S Lopez-Ortiz, K E Panter, J A Pfister, K L Launchbaugh. The effect of body condition on disposition of alkaloids from silvery lupine (Lupinus argenteus pursh) in sheep. Journal of animal science. 2004 Sep; 82(9):2798-805. doi: 10.2527/2004.8292798x. [PMID: 15446497]
  • Alice Martins, Michael Wink, Andreas Tei, Amélia P Rauter. Quinolizidine alkaloid profiles of two taxa of Teline maderensis. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2003 Nov; 58(11-12):776-8. doi: 10.1515/znc-2003-11-1203. [PMID: 14713148]
  • Ken-ichi Nihei, Kozo Shibata, Isao Kubo. (+)-2,3-dehydro-10-oxo-alpha-isosparteine in Uresiphita reversalis larvae fed on Cytisus monspessulanus leaves. Phytochemistry. 2002 Dec; 61(8):987-90. doi: 10.1016/s0031-9422(02)00398-9. [PMID: 12453531]
  • Shuang-Cheng Ma, Jiang Du, Paul Pui-Hay But, Xue-Long Deng, Yong-Wen Zhang, Vincent Eng-Choon Ooi, Hong-Xi Xu, Spencer Hon-Sun Lee, Song Fong Lee. Antiviral Chinese medicinal herbs against respiratory syncytial virus. Journal of ethnopharmacology. 2002 Feb; 79(2):205-11. doi: 10.1016/s0378-8741(01)00389-0. [PMID: 11801383]
  • J A Ortega, J Lazerson. Anagyrine-induced red cell aplasia, vascular anomaly, and skeletal dysplasia. The Journal of pediatrics. 1987 Jul; 111(1):87-9. doi: 10.1016/s0022-3476(87)80349-9. [PMID: 3110390]