manoalide (BioDeep_00000011578)

   

Marine Natural Products natural product


代谢物信息卡片


manoalide

化学式: C25H36O5 (416.2563)
中文名称: 4-[3,6-二氢-6-羟基-5-[4-甲基-6-(2,6,6-三甲基-1-环己烯-1-基)-3-己烯基]-2H-吡喃-2-基]-5-羟基-2(5H)-呋喃酮
谱图信息: 最多检出来源 Viridiplantae(plant) 9.18%

分子结构信息

SMILES: C1[C@](C)(C)C(CC/C(/C)=C/CCC2=CC[C@H](C3=CC(=O)OC3O)O[C@H]2O)=C(C)CC1
InChI: InChI=1S/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3/b16-7+/t21-,23-,24-/m1/s1

描述信息

A sesterterpenoid isolated from the marine sponge Luffariella variabilis and which has been shown to exhibit inhibitory activity towards phospholipase A2.
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D004791 - Enzyme Inhibitors > D010726 - Phosphodiesterase Inhibitors
D002317 - Cardiovascular Agents > D002121 - Calcium Channel Blockers
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
D000077264 - Calcium-Regulating Hormones and Agents
D049990 - Membrane Transport Modulators
D000893 - Anti-Inflammatory Agents
D018501 - Antirheumatic Agents

同义名列表

2 个代谢物同义名

manoalide; Manoalide



数据库引用编号

15 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 9 ALOX5, ANXA5, CASP3, EGFR, ELANE, ITPR3, PLA2G12A, PTGS2, TNK1
Peripheral membrane protein 4 ALOX5, ANXA5, PTGS2, TNK1
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 3 EGFR, ITPR3, PTGS2
Nucleus 4 CA9, CASP3, EGFR, PLCZ1
cytosol 7 ALOX5, ANXA5, CASP3, ELANE, IL1B, PLCZ1, PRKCQ
phagocytic vesicle 1 ELANE
nucleoplasm 5 ALOX5, ATP2B1, CASP3, ITPR3, PLCZ1
Cell membrane 4 ATP2B1, CA9, EGFR, TNF
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Multi-pass membrane protein 3 ATP2B1, CACNA1I, ITPR3
Synapse 1 ATP2B1
cell junction 1 EGFR
cell surface 3 EGFR, ELANE, TNF
glutamatergic synapse 3 ATP2B1, CASP3, EGFR
Golgi membrane 1 EGFR
neuronal cell body 3 CASP3, ITPR3, TNF
presynaptic membrane 1 ATP2B1
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 ALOX5, IL1B
Lysosome 1 IL1B
endosome 1 EGFR
plasma membrane 9 ATP2B1, CA9, CACNA1I, EGFR, F2, ITPR3, PRKCQ, TNF, TNK1
synaptic vesicle membrane 1 ATP2B1
Membrane 7 ANXA5, ATP2B1, CA9, CACNA1I, EGFR, ITPR3, TNK1
apical plasma membrane 1 EGFR
axon 1 CCK
basolateral plasma membrane 3 ATP2B1, CA9, EGFR
brush border 1 ITPR3
caveola 1 PTGS2
extracellular exosome 5 ANXA5, ATP2B1, ELANE, F2, SERPING1
endoplasmic reticulum 2 ITPR3, PTGS2
extracellular space 9 ALOX5, CCK, CXCL8, EGFR, ELANE, F2, IL1B, SERPING1, TNF
perinuclear region of cytoplasm 3 ALOX5, EGFR, PLCZ1
protein-containing complex 2 EGFR, PTGS2
intracellular membrane-bounded organelle 1 ATP2B1
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
pronucleus 1 PLCZ1
Single-pass type I membrane protein 2 CA9, EGFR
Secreted 5 CCK, CXCL8, F2, IL1B, PLA2G12A
extracellular region 10 ALOX5, ANXA5, CCK, CXCL8, ELANE, F2, IL1B, PLA2G12A, SERPING1, TNF
centriolar satellite 1 PRKCQ
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Nucleus membrane 1 ALOX5
nuclear membrane 2 ALOX5, EGFR
external side of plasma membrane 2 ANXA5, TNF
nucleolus 3 CA9, ITPR3, PLCZ1
apical part of cell 1 ITPR3
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 2 ALOX5, PLCZ1
Membrane raft 2 EGFR, TNF
focal adhesion 2 ANXA5, EGFR
intracellular vesicle 1 EGFR
sarcoplasmic reticulum 1 ITPR3
collagen-containing extracellular matrix 4 ANXA5, ELANE, F2, SERPING1
secretory granule 2 ELANE, IL1B
lateral plasma membrane 1 ATP2B1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 2 ITPR3, PTGS2
receptor complex 2 EGFR, ITPR3
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
cell projection 1 ATP2B1
phagocytic cup 1 TNF
Nucleus, nucleolus 1 CA9
blood microparticle 2 F2, SERPING1
Basolateral cell membrane 1 ATP2B1
Cell projection, microvillus membrane 1 CA9
microvillus membrane 1 CA9
nuclear envelope 1 ALOX5
Nucleus envelope 1 ALOX5
Presynaptic cell membrane 1 ATP2B1
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
ficolin-1-rich granule lumen 1 ALOX5
secretory granule lumen 1 ALOX5
secretory granule membrane 1 ITPR3
Golgi lumen 1 F2
endoplasmic reticulum lumen 3 F2, PTGS2, SERPING1
nuclear matrix 1 ALOX5
transcription repressor complex 1 ELANE
platelet alpha granule lumen 1 SERPING1
voltage-gated calcium channel complex 1 CACNA1I
specific granule lumen 1 ELANE
Secreted, extracellular exosome 1 IL1B
azurophil granule lumen 1 ELANE
immunological synapse 2 ATP2B1, PRKCQ
aggresome 1 PRKCQ
Nucleus matrix 1 ALOX5
nuclear envelope lumen 1 ALOX5
vesicle membrane 1 ANXA5
clathrin-coated endocytic vesicle membrane 1 EGFR
platelet dense tubular network membrane 1 ITPR3
death-inducing signaling complex 1 CASP3
Cytoplasmic vesicle, secretory vesicle membrane 1 ITPR3
Cytoplasmic vesicle, phagosome 1 ELANE
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
transport vesicle membrane 1 ITPR3
sperm head 1 PLCZ1
endothelial microparticle 1 ANXA5
Nucleus intermembrane space 1 ALOX5
photoreceptor ribbon synapse 1 ATP2B1
cytoplasmic side of endoplasmic reticulum membrane 1 ITPR3
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Ming Chen, Chie Aoki-Utsubo, Masanori Kameoka, Lin Deng, Yutaka Terada, Wataru Kamitani, Kei Sato, Yoshio Koyanagi, Makoto Hijikata, Keiko Shindo, Takeshi Noda, Michinori Kohara, Hak Hotta. Broad-spectrum antiviral agents: secreted phospholipase A2 targets viral envelope lipid bilayers derived from the endoplasmic reticulum membrane. Scientific reports. 2017 Nov; 7(1):15931. doi: 10.1038/s41598-017-16130-w. [PMID: 29162867]
  • E V Samoilova, A A Pirkova, N V Prokazova, A A Korotaeva. Effect of serum from cardiovascular patients on catalytic activity of secretory phospholipase A2 (IIA). Bulletin of experimental biology and medicine. 2006 Nov; 142(5):581-2. doi: 10.1007/s10517-006-0423-6. [PMID: 17415467]
  • Frédéric Dorandeu, Rémi Hesters, Fabien Girard, Elise Four, Annie Foquin, Cassian Bon, Guy Lallement, Grazyna Faure. Inhibition of crotoxin phospholipase A(2) activity by manoalide associated with inactivation of crotoxin toxicity and dissociation of the heterodimeric neurotoxic complex. Biochemical pharmacology. 2002 Feb; 63(4):755-61. doi: 10.1016/s0006-2952(01)00896-6. [PMID: 11992645]
  • K Shibata, H Yoshino, N Mizuno, H Shinohara, K Morita, S Kitayama, H Kurihara, T Dohi. Mediation by platelet-activating factor of 12-hydroxyeicosatetraenoic acid-induced cytosolic free calcium concentration elevation in neutrophils. Prostaglandins & other lipid mediators. 2000 Oct; 62(4):385-94. doi: 10.1016/s0090-6980(00)00090-3. [PMID: 11060901]
  • A Soejima, S Ishizuka, N Miyake, K Fukuoka, M Suzuki, Y Kamiya, T Nagasawa. Simultaneous inhibition of renal phospholipase A(2) and glutathione synthesis by manoalide and DL-buthionine sulfoximine induces acute tubular dysfunction in rats. Experimental nephrology. 2000 Mar; 8(2):84-90. doi: 10.1159/000020653. [PMID: 10729747]
  • J Y Miao, S Araki, H W Zhang, H Hayashi. Effect of manoalide on apoptosis induced by deprivation of growth factors in vascular endothelial cells. Zhongguo yao li xue bao = Acta pharmacologica Sinica. 1999 Feb; 20(2):121-5. doi: NULL. [PMID: 10437157]
  • A Pompeo, M Baldassare, A Luini, R Buccione. Cyclosporin A, but not FK506, increases arachidonic acid release and inhibits proliferation of pituitary corticotrope tumor cells. Life sciences. 1999; 64(10):837-46. doi: 10.1016/s0024-3205(99)00005-3. [PMID: 10096434]
  • E Grange, O Rabin, J Bell, M C Chang. Manoalide, a phospholipase A2 inhibitor, inhibits arachidonate incorporation and turnover in brain phospholipids of the awake rat. Neurochemical research. 1998 Oct; 23(10):1251-7. doi: 10.1023/a:1020788031720. [PMID: 9804280]
  • K B Glaser, Y W Lock. Regulation of prostaglandin H synthase 2 expression in human monocytes by the marine natural products manoalide and scalaradial. Novel effects independent of inhibition of lipid mediator production. Biochemical pharmacology. 1995 Sep; 50(7):913-22. doi: 10.1016/0006-2952(95)00211-h. [PMID: 7575673]
  • S Rotondo, A Celardo, V Evangelista, C Cerletti. The endoperoxides/TxA2 analogue, U46619, inhibits human polymorphonuclear leukocyte function. Journal of leukocyte biology. 1995 Jan; 57(1):72-9. doi: 10.1002/jlb.57.1.72. [PMID: 7829974]
  • P B Jacobson, D J Schrier. Regulation of CD11b/CD18 expression in human neutrophils by phospholipase A2. Journal of immunology (Baltimore, Md. : 1950). 1993 Nov; 151(10):5639-52. doi: . [PMID: 8228253]
  • R D Butcher, S J Wojcik, T Lints, T Wilson, P C Schofield, R Ralph. Arachidonic acid, a growth signal in murine P815 mastocytoma cells. Cancer research. 1993 Jul; 53(14):3405-10. doi: NULL. [PMID: 8391926]
  • S Muallem, P Loessberg, G Sachs, L A Wheeler. Agonist-sensitive and -insensitive intracellular Ca2+ pools. Separate Ca(2+)-releasing mechanisms revealed by manoalide and benzohydroquinone. The Biochemical journal. 1991 Oct; 279 ( Pt 2)(?):367-75. doi: 10.1042/bj2790367. [PMID: 1659378]
  • C J Long, H M Sarau, B A Berkowitz. The inhibition of release of endothelium-derived relaxant factor by manoalide, a potent inhibitor of phospholipase A2. British journal of pharmacology. 1987 Dec; 92(4):843-9. doi: 10.1111/j.1476-5381.1987.tb11389.x. [PMID: 2827828]
  • C F Bennett, S Mong, M A Clarke, L I Kruse, S T Crooke. Differential effects of manoalide on secreted and intracellular phospholipases. Biochemical pharmacology. 1987 Mar; 36(5):733-40. doi: 10.1016/0006-2952(87)90727-1. [PMID: 3103628]