Trilobacin (BioDeep_00000007797)

 

Secondary id: BioDeep_00000843899, BioDeep_00001869761

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


3-(2,13-dihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-5-methyl-2,5-dihydrofuran-2-one

化学式: C37H66O7 (622.4808)
中文名称: 番荔枝宁VI
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 13.53%

分子结构信息

SMILES: CCCCCCCCCCC(C1CCC(O1)C2CCC(O2)C(CCCCCCCCCCC(CC3=CC(OC3=O)C)O)O)O
InChI: InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3/t28-,30-,31+,32+,33+,34+,35+,36+/m0/s1

描述信息

Isolated from Asimina triloba (pawpaw), Annona squamosa (sugar apple), Annona purpurea (soncoya) and Rollinia mucosa (biriba). Asimicin is found in many foods, some of which are fruits, alcoholic beverages, sugar apple, and beverages.
Bullatacin is found in alcoholic beverages. Bullatacin is isolated from Rollinia mucosa (biriba), Annona squamosa (sugar apple) and Annona reticulata (custard apple).
D010575 - Pesticides > D007306 - Insecticides
D000970 - Antineoplastic Agents
D016573 - Agrochemicals

同义名列表

9 个代谢物同义名

3-(2,13-dihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-5-methyl-2,5-dihydrofuran-2-one; 3-(2,13-dihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-5-methyl-5H-furan-2-one; Rolliniastatin-2; annonin VI; Trilobacin; Bullatacin; Asimicin; Squamocin; Asimicin



数据库引用编号

27 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)

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 15 ABCB1, ANXA5, BCL2, BCL2L1, CALR, CASP3, CASP8, CCM2, CRYZ, HMGB1, MSMP, MYC, NQO1, SLC9A1, TUBB4B
Peripheral membrane protein 4 ANXA5, HMGB1, NDUFA5, NDUFA7
Endoplasmic reticulum membrane 2 BCL2, CALR
Mitochondrion membrane 1 BCL2L1
Nucleus 10 BCL2, CALR, CASP3, CASP8, FOS, HMGB1, MYC, NQO1, PARP1, TUBB4B
cytosol 11 ANXA5, BCL2, BCL2L1, CALR, CASP3, CASP8, CRYZ, FOS, NQO1, PARP1, TUBB4B
dendrite 1 NQO1
nuclear body 1 PARP1
centrosome 1 BCL2L1
nucleoplasm 7 CASP3, CASP8, FOS, HMGB1, MYC, PARP1, SLC9A1
RNA polymerase II transcription regulator complex 1 FOS
Cell membrane 3 ABCB1, HMGB1, SLC9A1
Cytoplasmic side 1 BCL2L1
lamellipodium 2 CASP8, SLC9A1
Multi-pass membrane protein 2 ABCB1, SLC9A1
Synapse 1 NQO1
cell surface 4 ABCB1, CALR, HMGB1, SLC9A1
glutamatergic synapse 2 CALR, CASP3
mitochondrial inner membrane 3 BCL2L1, NDUFA5, NDUFA7
neuronal cell body 2 CASP3, NQO1
postsynapse 1 CALR
sarcolemma 1 ANXA5
smooth endoplasmic reticulum 1 CALR
Cytoplasm, cytosol 4 BCL2L1, CALR, NQO1, PARP1
acrosomal vesicle 1 CALR
endosome 1 HMGB1
plasma membrane 3 ABCB1, HMGB1, SLC9A1
synaptic vesicle membrane 1 BCL2L1
Membrane 8 ABCB1, ANXA5, BCL2, CALR, MYC, NQO1, PARP1, SLC9A1
apical plasma membrane 2 ABCB1, SLC9A1
basolateral plasma membrane 1 SLC9A1
extracellular exosome 6 ABCB1, ANXA5, CALR, CRYZ, SLC9A1, TUBB4B
endoplasmic reticulum 5 BCL2, BCL2L1, CALR, FOS, HMGB1
extracellular space 3 CALR, HMGB1, MSMP
perinuclear region of cytoplasm 2 CALR, SLC9A1
intercalated disc 1 SLC9A1
mitochondrion 10 BCL2, BCL2L1, CASP8, CCM2, CRYZ, NDUFA5, NDUFA7, PARP1, RTL10, SLC9A1
protein-containing complex 5 BCL2, CASP8, CCM2, MYC, PARP1
postsynaptic density 1 CASP3
Secreted 2 HMGB1, MSMP
extracellular region 4 ANXA5, CALR, HMGB1, TUBB4B
Mitochondrion outer membrane 2 BCL2, BCL2L1
Single-pass membrane protein 2 BCL2, BCL2L1
mitochondrial outer membrane 3 BCL2, BCL2L1, CASP8
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 1 BCL2L1
Extracellular side 1 HMGB1
transcription regulator complex 1 PARP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 BCL2L1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 2 BCL2, BCL2L1
Bcl-2 family protein complex 2 BCL2, BCL2L1
nuclear membrane 2 BCL2, BCL2L1
external side of plasma membrane 2 ANXA5, CALR
Extracellular vesicle 1 TUBB4B
Secreted, extracellular space, extracellular matrix 1 CALR
T-tubule 1 SLC9A1
microtubule cytoskeleton 1 TUBB4B
nucleolus 2 MYC, PARP1
Apical cell membrane 1 ABCB1
Cell projection, lamellipodium 1 CASP8
Mitochondrion inner membrane 2 NDUFA5, NDUFA7
Matrix side 2 NDUFA5, NDUFA7
Membrane raft 1 SLC9A1
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 TUBB4B
focal adhesion 3 ANXA5, CALR, SLC9A1
microtubule 1 TUBB4B
collagen-containing extracellular matrix 2 ANXA5, CALR
Zymogen granule membrane 1 ANXA5
chromatin 3 FOS, MYC, PARP1
phagocytic vesicle membrane 1 CALR
mitotic spindle 1 TUBB4B
Chromosome 2 HMGB1, PARP1
cytoskeleton 2 CASP8, TUBB4B
Nucleus, nucleolus 2 MYC, PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
Basolateral cell membrane 1 SLC9A1
site of double-strand break 1 PARP1
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
nuclear envelope 3 CALR, MYC, PARP1
axonemal microtubule 1 TUBB4B
Nucleus, nucleoplasm 1 MYC
cell body 1 CASP8
myelin sheath 1 BCL2
respiratory chain complex I 2 NDUFA5, NDUFA7
ficolin-1-rich granule lumen 1 HMGB1
secretory granule lumen 1 HMGB1
endoplasmic reticulum quality control compartment 1 CALR
endoplasmic reticulum lumen 1 CALR
nuclear matrix 1 FOS
transcription repressor complex 1 HMGB1
RNA polymerase II transcription repressor complex 1 MYC
azurophil granule lumen 1 TUBB4B
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 CALR
vesicle membrane 1 ANXA5
Sarcoplasmic reticulum lumen 1 CALR
endoplasmic reticulum-Golgi intermediate compartment 1 HMGB1
protein-DNA complex 2 FOS, PARP1
external side of apical plasma membrane 1 ABCB1
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
lumenal side of endoplasmic reticulum membrane 1 CALR
MHC class I peptide loading complex 1 CALR
Rough endoplasmic reticulum 1 MYC
condensed chromosome 1 HMGB1
site of DNA damage 1 PARP1
endocytic vesicle lumen 1 CALR
ribosome 1 CALR
transcription factor AP-1 complex 1 FOS
Myc-Max complex 1 MYC
alphav-beta3 integrin-HMGB1 complex 1 HMGB1
Cytoplasmic vesicle, secretory vesicle, Cortical granule 1 CALR
cortical granule 1 CALR
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
Cytolytic granule 1 CALR
BAD-BCL-2 complex 1 BCL2
cation-transporting ATPase complex 1 SLC9A1
[Isoform Bcl-X(L)]: Mitochondrion inner membrane 1 BCL2L1
nucleoplasmic reticulum 1 MYC


文献列表

  • Claudia Azucena Durán-Ruiz, Rocío Cruz-Ortega, Alejandro Zaldívar-Riverón, Hilda Araceli Zavaleta-Mancera, Iván De-la-Cruz-Chacón, Alma Rosa González-Esquinca. Ontogenic synchronization of Bephratelloides cubensis, Annona macroprophyllata seeds and acetogenins from Annonaceae. Journal of plant research. 2019 Jan; 132(1):81-91. doi: 10.1007/s10265-018-01078-3. [PMID: 30607643]
  • Jing-Fang Shi, Ping Wu, Zi-Hua Jiang, Xiao-Yi Wei. Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins. European journal of medicinal chemistry. 2014 Jan; 71(?):219-28. doi: 10.1016/j.ejmech.2013.11.012. [PMID: 24308999]
  • Yong Chen, Sha-sha Xu, Jian-wei Chen, Yu Wang, Hui-qing Xu, Nai-bing Fan, Xiang Li. Anti-tumor activity of Annona squamosa seeds extract containing annonaceous acetogenin compounds. Journal of ethnopharmacology. 2012 Jul; 142(2):462-6. doi: 10.1016/j.jep.2012.05.019. [PMID: 22609808]
  • Yong Chen, Jian-wei Chen, Shi-jia Liu, Chun-lei Xu, Hui-qing Xu, Bao-chang Cai, Xiang Li, Wen-zheng Ju. Determination of bullatacin in rat plasma by liquid chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 May; 897(?):94-7. doi: 10.1016/j.jchromb.2012.03.044. [PMID: 22534655]
  • Kirk W Pomper, Jeremiah D Lowe, Sheri B Crabtree, William Keller. Identification of annonaceous acetogenins in the ripe fruit of the North American pawpaw ( Asimina triloba ). Journal of agricultural and food chemistry. 2009 Sep; 57(18):8339-43. doi: 10.1021/jf9018239. [PMID: 19711911]
  • Azucena González-Coloma, Ana Guadaño, Concepción de Inés, Rafael Martínez-Díaz, Diego Cortes. Selective action of acetogenin mitochondrial complex I inhibitors. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2002 Nov; 57(11-12):1028-34. doi: 10.1515/znc-2002-11-1213. [PMID: 12562089]
  • J R Tormo, M C González, D Cortes, E Estornell. Kinetic characterization of mitochondrial complex I inhibitors using annonaceous acetogenins. Archives of biochemistry and biophysics. 1999 Sep; 369(1):119-26. doi: 10.1006/abbi.1999.1343. [PMID: 10462447]
  • Y Chen, D Q Yu. [Classification and NMR characteristics of the gamma-lactone and THF rings of antitumor bioactive Annonaceous acetogenins]. Yao xue xue bao = Acta pharmaceutica Sinica. 1998 Jul; 33(7):553-60. doi: ". [PMID: 12016892]
  • H Shimada, J B Grutzner, J F Kozlowski, J L McLaughlin. Membrane conformations and their relation to cytotoxicity of asimicin and its analogues. Biochemistry. 1998 Jan; 37(3):854-66. doi: 10.1021/bi972348l. [PMID: 9454575]
  • E Estornell, J R Tormo, D Cortes. Cherimolin-1, new selective inhibitor of the first energy-coupling site of the NADH: ubiquinone oxidoreductase (complex I). Biochemical and biophysical research communications. 1997 Nov; 240(1):234-8. doi: 10.1006/bbrc.1997.7637. [PMID: 9367916]
  • D J Morré, R de Cabo, C Farley, N H Oberlies, J L McLaughlin. Mode of action of bullatacin, a potent antitumor acetogenin: inhibition of NADH oxidase activity of HeLa and HL-60, but not liver, plasma membranes. Life sciences. 1995; 56(5):343-8. doi: 10.1016/0024-3205(94)00957-0. [PMID: 7837933]
  • X H Li, Y H Hui, J K Rupprecht, Y M Liu, K V Wood, D L Smith, C J Chang, J L McLaughlin. Bullatacin, bullatacinone, and squamone, a new bioactive acetogenin, from the bark of Annona squamosa. Journal of natural products. 1990 Jan; 53(1):81-6. doi: 10.1021/np50067a010. [PMID: 2348205]