Cytochalasin B (BioDeep_00000013151)
natural product PANOMIX_OTCML-2023
代谢物信息卡片
2H-Oxacyclotetradec(2,3-d)isoindole-2,18(5H)-dione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-, (E,E)-(5S,9R,12aS,13S,15S,15aS,16S,18aS)-
化学式: C29H37NO5 (479.26715920000004)
中文名称: 细胞松弛素 B
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 0.98%
分子结构信息
SMILES: C=C1C(C)C2C(Cc3ccccc3)NC(=O)C23OC(=O)C=CC(O)CCCC(C)CC=CC3C1O
InChI: InChI=1S/C29H37NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1
描述信息
An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.
D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins
Cytochalasin B is a cell-permeable mycotoxin binding to the barbed end of actin filaments, disrupting the formation of actin polymers, with Kd value of 1.4-2.2 nM for F-actin. Cytochalasin B blocks cell migration.
同义名列表
7 个代谢物同义名
7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione; Cytochalasin B; 2H-Oxacyclotetradec(2,3-d)isoindole-2,18(5H)-dione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-, (E,E)-(5S,9R,12aS,13S,15S,15aS,16S,18aS)-; Cytochalasin B - CASMI2016 Category 1 - Challenge 8; Cytochalasin B - CASMI2016 Category 1 - Challenge 3; Neuro_000052; Phomin
数据库引用编号
23 个数据库交叉引用编号
- ChEBI: CHEBI:95007
- ChEBI: CHEBI:23527
- KEGG: C19954
- PubChem: 44634701
- PubChem: 5311281
- PubChem: 5836499
- PubChem: 2919
- Metlin: METLIN46771
- ChEMBL: CHEMBL1554187
- ChEMBL: CHEMBL411729
- LipidMAPS: LMPK11000002
- MeSH: Cytochalasin B
- KNApSAcK: C00011322
- CAS: 14930-96-2
- CAS: 11032-95-4
- MoNA: CCMSLIB00000579297
- MoNA: CCMSLIB00000579293
- PMhub: MS000027556
- MetaboLights: MTBLC23527
- PubChem: 135626420
- PDB-CCD: 5RH
- RefMet: Cytochalasin B
- medchemexpress: HY-16928
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)
8 个相关的物种来源信息
- 749465 - Boeremia exigua:
- 41550 - Cirsium arvense: 10.1016/J.TET.2010.12.058
- 37463 - Phoma: 10.1016/J.BMCL.2012.03.058
- 2211333 - Pyrenophora biseptata: 10.1016/S0031-9422(02)00071-7
- 139229 - Pyrenophora dematioidea: 10.1016/S0031-9422(02)00071-7
- 91370 - Pyrenophora seminiperda: 10.1016/S0031-9422(02)00071-7
- 50192 - Sonchus arvensis: 10.1016/J.PHYTOCHEM.2007.11.003
- 381734 - Sonchus mauritanicus: 10.1016/J.PHYTOCHEM.2007.11.003
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。
文献列表
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Nature communications.
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2021 12; 14(1):. doi:
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Molecular pharmaceutics.
2021 03; 18(3):1080-1092. doi:
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Scientific reports.
2020 07; 10(1):10740. doi:
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10.1007/s12038-010-0060-0. [PMID: 21289434] - Kusumarn Noipha, Tula Thongthoom, Uraiwan Songsiang, Chantana Boonyarat, Chavi Yenjai. Carbazoles and coumarins from Clausena harmandiana stimulate glucose uptake in L6 myotubes.
Diabetes research and clinical practice.
2010 Dec; 90(3):e67-71. doi:
10.1016/j.diabres.2010.09.005. [PMID: 20888659] - Martina Königer, Brita Jessen, Rui Yang, Dorothea Sittler, Gary C Harris. Light, genotype, and abscisic acid affect chloroplast positioning in guard cells of Arabidopsis thaliana leaves in distinct ways.
Photosynthesis research.
2010 Sep; 105(3):213-27. doi:
10.1007/s11120-010-9580-6. [PMID: 20614182] - Anthony J Cura, Anthony Carruthers. Acute modulation of sugar transport in brain capillary endothelial cell cultures during activation of the metabolic stress pathway.
The Journal of biological chemistry.
2010 May; 285(20):15430-15439. doi:
10.1074/jbc.m110.110593. [PMID: 20231288] - Anna-Karin Johnsson, Roger Karlsson. Microtubule-dependent localization of profilin I mRNA to actin polymerization sites in serum-stimulated cells.
European journal of cell biology.
2010 May; 89(5):394-401. doi:
10.1016/j.ejcb.2009.10.020. [PMID: 20129697] - Adel S Al-Zubairi, Ahmad Bustamam Abdul, M M Syam. Evaluation of the genotoxicity of zerumbone in cultured human peripheral blood lymphocytes.
Toxicology in vitro : an international journal published in association with BIBRA.
2010 Apr; 24(3):707-12. doi:
10.1016/j.tiv.2010.01.011. [PMID: 20123012] - Duc M Vu, Haruchika Masuda, Tun A Yokoyama, Satoshi Fujimura, Michiru Kobori, Rie Ito, Kaichiro Sawada, Akira Saito, Takayuki Asahara. CD133+ endothelial progenitor cells as a potential cell source for a bioartificial glomerulus.
Tissue engineering. Part A.
2009 Oct; 15(10):3173-82. doi:
10.1089/ten.tea.2009.0050. [PMID: 19358628] - Qingyong Chen, Guohua Lu, Yanyi Wang, Yingke Xu, Ying Zheng, Li Yan, Zhongyong Jiang, Ling Yang, Jianwei Zhan, Yuquan Wu, Jianying Zhou. Cytoskeleton disorganization during apoptosis induced by curcumin in A549 lung adenocarcinoma cells.
Planta medica.
2009 Jun; 75(8):808-13. doi:
10.1055/s-0029-1185399. [PMID: 19266427] - Panagiotis Apostolakos, Pantelis Livanos, Basil Galatis. Microtubule involvement in the deposition of radial fibrillar callose arrays in stomata of the fern Asplenium nidus L.
Cell motility and the cytoskeleton.
2009 Jun; 66(6):342-9. doi:
10.1002/cm.20366. [PMID: 19363785] - Carlos A Marra, María J T de Alaniz. Microtubule depolymerization modifies the incorporation of fatty acids into glycerolipids.
Medical science monitor : international medical journal of experimental and clinical research.
2009 Jun; 15(6):BR157-65. doi:
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Biomaterials.
2009 May; 30(13):2440-8. doi:
10.1016/j.biomaterials.2009.01.019. [PMID: 19215978] - Guang-Bin Zhou, Ning Li. Cryopreservation of porcine oocytes: recent advances.
Molecular human reproduction.
2009 May; 15(5):279-85. doi:
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Physiologia plantarum.
2009 May; 136(1):45-56. doi:
10.1111/j.1399-3054.2009.01212.x. [PMID: 19508367] - Sonia Scarfì, Mirko Magnone, Chiara Ferraris, Marina Pozzolini, Federica Benvenuto, Umberto Benatti, Marco Giovine. Ascorbic acid pre-treated quartz stimulates TNF-alpha release in RAW 264.7 murine macrophages through ROS production and membrane lipid peroxidation.
Respiratory research.
2009 Mar; 10(?):25. doi:
10.1186/1465-9921-10-25. [PMID: 19298665] - Souhila Medjkane, Cristina Perez-Sanchez, Cedric Gaggioli, Erik Sahai, Richard Treisman. Myocardin-related transcription factors and SRF are required for cytoskeletal dynamics and experimental metastasis.
Nature cell biology.
2009 Mar; 11(3):257-68. doi:
10.1038/ncb1833. [PMID: 19198601] - Mileva Ratko Karabasil, Takahiro Hasegawa, Ahmad Azlina, Nunuk Purwanti, Javkhlan Purevjav, Chenjuan Yao, Tetsuya Akamatsu, Kazuo Hosoi. Trafficking of GFP-AQP5 chimeric proteins conferred with unphosphorylated amino acids at their PKA-target motif ((152)SRRTS) in MDCK-II cells.
The journal of medical investigation : JMI.
2009 Feb; 56(1-2):55-63. doi:
10.2152/jmi.56.55. [PMID: 19262015] - Masha Prager-Khoutorsky, Micha E Spira. Neurite retraction and regrowth regulated by membrane retrieval, membrane supply, and actin dynamics.
Brain research.
2009 Jan; 1251(?):65-79. doi:
10.1016/j.brainres.2008.10.049. [PMID: 19022228] - A V Sudarikova, V I Chubinskiĭ-Nadezhdin, Iu A Neguliaev, E A Morachevskaia. [Functional properties of sodium channels in cholesterol-depleted K562 cells].
Tsitologiia.
2009; 51(8):676-83. doi:
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Cancer chemotherapy and pharmacology.
2008 Nov; 62(6):977-84. doi:
10.1007/s00280-008-0687-9. [PMID: 18274748] - M Casartelli, G Cermenati, S Rodighiero, F Pennacchio, B Giordana. A megalin-like receptor is involved in protein endocytosis in the midgut of an insect (Bombyx mori, Lepidoptera).
American journal of physiology. Regulatory, integrative and comparative physiology.
2008 Oct; 295(4):R1290-300. doi:
10.1152/ajpregu.00036.2008. [PMID: 18635456] - Tsung-Hsien Chou, Ih-Sheng Chen, Tsong-Long Hwang, Tai-Chi Wang, Tzong-Huei Lee, Lin-Yang Cheng, Ya-Chih Chang, Jui-Ying Cho, Jih-Jung Chen. Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils.
Journal of natural products.
2008 Oct; 71(10):1692-5. doi:
10.1021/np8004503. [PMID: 18817445] - Chao-Kuen Lai, King-Song Jeng, Keigo Machida, Michael M C Lai. Association of hepatitis C virus replication complexes with microtubules and actin filaments is dependent on the interaction of NS3 and NS5A.
Journal of virology.
2008 Sep; 82(17):8838-48. doi:
10.1128/jvi.00398-08. [PMID: 18562541] - Alessio Cimmino, Anna Andolfi, Alexander Berestetskiy, Antonio Evidente. Production of phytotoxins by Phoma exigua var. exigua, a potential mycoherbicide against perennial thistles.
Journal of agricultural and food chemistry.
2008 Aug; 56(15):6304-9. doi:
10.1021/jf8004178. [PMID: 18598037] - Scott A John, Michela Ottolia, James N Weiss, Bernard Ribalet. Dynamic modulation of intracellular glucose imaged in single cells using a FRET-based glucose nanosensor.
Pflugers Archiv : European journal of physiology.
2008 May; 456(2):307-22. doi:
10.1007/s00424-007-0395-z. [PMID: 18071748] - Vanda Pinto, Maria João Pinho, Ulrich Hopfer, Pedro A Jose, Patrício Soares-da-Silva. Oxidative stress and the genomic regulation of aldosterone-stimulated NHE1 activity in SHR renal proximal tubular cells.
Molecular and cellular biochemistry.
2008 Mar; 310(1-2):191-201. doi:
10.1007/s11010-007-9680-6. [PMID: 18095144] - Jih-Jung Chen, Tzu-Ying Wang, Tsong-Long Hwang. Neolignans, a coumarinolignan, lignan derivatives, and a chromene: anti-inflammatory constituents from Zanthoxylum avicennae.
Journal of natural products.
2008 Feb; 71(2):212-7. doi:
10.1021/np070594k. [PMID: 18211005] - Antoine T Chalfoun, Sawsan Ibrahim Kreydiyyeh. Involvement of the cytoskeleton in the effect of PGE2 on ion transport in the rat distal colon.
Prostaglandins & other lipid mediators.
2008 Feb; 85(1-2):58-64. doi:
10.1016/j.prostaglandins.2007.10.008. [PMID: 18096422] - Liane M Correa, Alysia Thomas, Stuart A Meyers. The macaque sperm actin cytoskeleton reorganizes in response to osmotic stress and contributes to morphological defects and decreased motility.
Biology of reproduction.
2007 Dec; 77(6):942-53. doi:
10.1095/biolreprod.107.060533. [PMID: 17823088] - Yong-Jie Ma, Hong-Chen Gu. Study on the endocytosis and the internalization mechanism of aminosilane-coated Fe3O4 nanoparticles in vitro.
Journal of materials science. Materials in medicine.
2007 Nov; 18(11):2145-9. doi:
10.1007/s10856-007-3015-8. [PMID: 17665123] - Lucia Formigli, Elisabetta Meacci, Chiara Sassoli, Roberta Squecco, Daniele Nosi, Flaminia Chellini, Fabio Naro, Fabio Francini, Sandra Zecchi-Orlandini. Cytoskeleton/stretch-activated ion channel interaction regulates myogenic differentiation of skeletal myoblasts.
Journal of cellular physiology.
2007 May; 211(2):296-306. doi:
10.1002/jcp.20936. [PMID: 17295211] - C G Walker, J M Bryson, D P Hancock, I D Caterson. Leptin secretion is related to glucose-derived lipogenesis in isolated adipocytes.
International journal of obesity (2005).
2007 Apr; 31(4):723-9. doi:
10.1038/sj.ijo.0803462. [PMID: 16953252] - Y-L Lai, J-C Lin, S-F Yang, T-Y Liu, S-L Hung. Areca nut extracts reduce the intracellular reactive oxygen species and release of myeloperoxidase by human polymorphonuclear leukocytes.
Journal of periodontal research.
2007 Feb; 42(1):69-76. doi:
10.1111/j.1600-0765.2006.00917.x. [PMID: 17214642] - Mukesh Kumar Gupta, Sang Jun Uhm, Hoon Taek Lee. Cryopreservation of immature and in vitro matured porcine oocytes by solid surface vitrification.
Theriogenology.
2007 Jan; 67(2):238-48. doi:
10.1016/j.theriogenology.2006.07.015. [PMID: 16963114] - Lingzhi Bao, Shaopeng Chen, Lijun Wu, Tom K Hei, Yuejin Wu, Zengliang Yu, An Xu. Mutagenicity of diesel exhaust particles mediated by cell-particle interaction in mammalian cells.
Toxicology.
2007 Jan; 229(1-2):91-100. doi:
10.1016/j.tox.2006.10.007. [PMID: 17147977] - Kathryn M Wright, Nicola T Wood, Alison G Roberts, Sean Chapman, Petra Boevink, Katrin M Mackenzie, Karl J Oparka. Targeting of TMV movement protein to plasmodesmata requires the actin/ER network: evidence from FRAP.
Traffic (Copenhagen, Denmark).
2007 Jan; 8(1):21-31. doi:
10.1111/j.1600-0854.2006.00510.x. [PMID: 17132144] - Emmanuel Panteris, Panagiotis Apostolakos, Basil Galatis. Cytoskeletal asymmetry in Zea mays subsidiary cell mother cells: a monopolar prophase microtubule half-spindle anchors the nucleus to its polar position.
Cell motility and the cytoskeleton.
2006 Nov; 63(11):696-709. doi:
10.1002/cm.20155. [PMID: 16986138] - Sanjeev Noel, Madhu Kasinathan, Srikanta Kumar Rath. Evaluation of apigenin using in vitro cytochalasin blocked micronucleus assay.
Toxicology in vitro : an international journal published in association with BIBRA.
2006 Oct; 20(7):1168-72. doi:
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FEBS letters.
2006 Sep; 580(20):4865-71. doi:
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Theriogenology.
2006 Jul; 66(2):415-22. doi:
10.1016/j.theriogenology.2005.11.023. [PMID: 16464491] - V V Roshchina. [Chemical signaling in plant microspore cells].
Izvestiia Akademii nauk. Seriia biologicheskaia.
2006 Jul; ?(4):414-20. doi:
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Journal of theoretical biology.
2006 Jun; 240(3):368-73. doi:
10.1016/j.jtbi.2005.09.020. [PMID: 16277995] - M A Silvestre, J Yániz, I Salvador, P Santolaria, F López-Gatius. Vitrification of pre-pubertal ovine cumulus-oocyte complexes: effect of cytochalasin B pre-treatment.
Animal reproduction science.
2006 Jun; 93(1-2):176-82. doi:
10.1016/j.anireprosci.2005.08.006. [PMID: 16169689] - Joseph G Wann, Chien-Sheng Lin, Li-Chien Chang, Yung-Ho Hsu, Chiang-Ting Chien, Deborah W Tai, Jin-Shuen Chen, Chih-Ching Yang, Lai-King Yeung, Chau-Fong Chen. Enhanced expression of glucose transporter 1 on erythrocyte membrane in hemodialysis patients: the possible role in erythrocyte ascorbate recycling.
American journal of kidney diseases : the official journal of the National Kidney Foundation.
2006 Jun; 47(6):1055-63. doi:
10.1053/j.ajkd.2006.02.190. [PMID: 16731301] - Nanako Ishimoto, Takayuki Nemoto, Keiko Nagayoshi, Fumiyoshi Yamashita, Mitsuru Hashida. Improved anti-oxidant activity of superoxide dismutase by direct chemical modification.
Journal of controlled release : official journal of the Controlled Release Society.
2006 Mar; 111(1-2):204-11. doi:
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