Perillic acid (BioDeep_00000405589)

Main id: BioDeep_00000001690

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


Perillic acid

化学式: C10H14O2 (166.0994)
中文名称: 紫苏酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CC(C(=C)C)CC=C1C(=O)O
InChI: InChI=1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)

描述信息

C471 - Enzyme Inhibitor > C2020 - Farnesyl Transferase Inhibitor

同义名列表

2 个代谢物同义名

Perillic acid; Perillic acid



数据库引用编号

14 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)

28 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 7 CASP3, CCND1, FNTA, MAPK14, PIK3C3, RHOA, TNK1
Peripheral membrane protein 1 TNK1
Endoplasmic reticulum membrane 2 HMGCR, RHOA
Cytoplasmic vesicle, autophagosome 1 PIK3C3
Nucleus 6 CASP3, CCND1, MAPK14, MMP2, PARP1, RHOA
autophagosome 1 PIK3C3
cytosol 9 CASP3, CCND1, FNTA, GPT, MAPK14, NGF, PARP1, PIK3C3, RHOA
dendrite 1 NGF
nuclear body 1 PARP1
phosphatidylinositol 3-kinase complex, class III 1 PIK3C3
centrosome 1 CCND1
nucleoplasm 4 CASP3, CCND1, MAPK14, PARP1
Cell membrane 2 RHOA, TNF
Lipid-anchor 1 RHOA
Cytoplasmic side 1 RHOA
Cleavage furrow 1 RHOA
lamellipodium 1 RHOA
ruffle membrane 1 RHOA
Multi-pass membrane protein 1 HMGCR
cell cortex 1 RHOA
cell junction 1 RHOA
cell surface 1 TNF
glutamatergic synapse 4 CASP3, MAPK14, PIK3C3, RHOA
neuronal cell body 2 CASP3, TNF
postsynapse 1 RHOA
synaptic vesicle 1 NGF
Cytoplasm, cytosol 1 PARP1
endosome 2 PIK3C3, RHOA
plasma membrane 6 CSF2, FNTA, MMP2, RHOA, TNF, TNK1
Membrane 4 HMGCR, PARP1, PIK3C3, TNK1
axon 1 NGF
extracellular exosome 3 GPT, MMP9, RHOA
endoplasmic reticulum 1 HMGCR
extracellular space 8 CSF2, IL10, IL2, IL6, MMP2, MMP9, NGF, TNF
bicellular tight junction 1 CCND1
mitochondrion 3 MAPK14, MMP2, PARP1
protein-containing complex 1 PARP1
intracellular membrane-bounded organelle 1 CSF2
postsynaptic density 1 CASP3
Secreted 5 CSF2, IL10, IL2, IL6, NGF
extracellular region 9 CSF2, IL10, IL2, IL6, MAPK14, MMP2, MMP9, NGF, TNF
cytoplasmic side of plasma membrane 1 RHOA
transcription regulator complex 1 PARP1
Nucleus membrane 1 CCND1
nuclear membrane 1 CCND1
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 1 MMP9
dendritic spine 1 RHOA
nucleolus 1 PARP1
midbody 2 PIK3C3, RHOA
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 RHOA
Cell projection, lamellipodium 1 RHOA
Membrane raft 1 TNF
focal adhesion 1 RHOA
GABA-ergic synapse 1 PIK3C3
extracellular matrix 1 MMP2
Peroxisome 1 PIK3C3
peroxisomal membrane 1 HMGCR
collagen-containing extracellular matrix 2 MMP2, MMP9
axoneme 1 PIK3C3
nuclear speck 1 MAPK14
Late endosome 1 PIK3C3
sarcomere 1 MMP2
chromatin 1 PARP1
microtubule associated complex 1 FNTA
phagocytic cup 1 TNF
phagocytic vesicle membrane 1 PIK3C3
cell periphery 1 RHOA
Chromosome 1 PARP1
cytoskeleton 1 RHOA
Nucleus, nucleolus 1 PARP1
spindle pole 1 MAPK14
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
Cytoplasm, cell cortex 1 RHOA
site of double-strand break 1 PARP1
nuclear envelope 1 PARP1
endosome lumen 1 NGF
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
Cell projection, dendrite 1 RHOA
Peroxisome membrane 1 HMGCR
ficolin-1-rich granule lumen 2 MAPK14, MMP9
secretory granule lumen 1 MAPK14
secretory granule membrane 1 RHOA
Golgi lumen 1 NGF
endoplasmic reticulum lumen 1 IL6
transcription repressor complex 1 CCND1
tertiary granule lumen 1 MMP9
[Isoform 1]: Secreted, extracellular space, extracellular matrix 1 MMP2
presynaptic endosome 1 PIK3C3
protein-DNA complex 1 PARP1
ficolin-1-rich granule membrane 1 RHOA
death-inducing signaling complex 1 CASP3
apical junction complex 1 RHOA
granulocyte macrophage colony-stimulating factor receptor complex 1 CSF2
site of DNA damage 1 PARP1
cyclin-dependent protein kinase holoenzyme complex 1 CCND1
postsynaptic endosome 1 PIK3C3
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
Autolysosome 1 PIK3C3
interleukin-6 receptor complex 1 IL6
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
cyclin D1-CDK4 complex 1 CCND1
cyclin D1-CDK6 complex 1 CCND1
CAAX-protein geranylgeranyltransferase complex 2 FNTA, PGGT1B
protein farnesyltransferase complex 1 FNTA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yao Huang, Haiquan Yang, Wei Shen, Yuanyuan Xia, Yu Cao, Xianzhong Chen. [Production of limonene and its derivative in Saccharomyces cerevisiae via metabolic engineering]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2023 Nov; 39(11):4647-4662. doi: 10.13345/j.cjb.230181. [PMID: 38013190]
  • 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]
  • Juliane da Silva Santos, Camila Diedrich, Christiane Schineider Machado, Clovis Orlando da Fonseca, Najeh Maissar Khalil, Rubiana Mara Mainardes. Intranasal administration of perillyl alcohol-loaded nanoemulsion and pharmacokinetic study of its metabolite perillic acid in plasma and brain of rats using ultra-performance liquid chromatography/tandem mass spectrometry. Biomedical chromatography : BMC. 2021 Apr; 35(4):e5037. doi: 10.1002/bmc.5037. [PMID: 33238042]
  • Daniela Carneiro de Lima, Silvana Vianna Rodrigues, Gilson Teles Boaventura, Hee-Yeon Cho, Thomas C Chen, Axel H Schönthal, Clovis Orlando Da Fonseca. Simultaneous measurement of perillyl alcohol and its metabolite perillic acid in plasma and lung after inhalational administration in Wistar rats. Drug testing and analysis. 2020 Feb; 12(2):268-279. doi: 10.1002/dta.2722. [PMID: 31800149]
  • Naoya Kitamura, Machiko Nishino, Akihiko Fujii, Kohjiro Hashizume, Junji Nakamura, Hidehiko Kondo, Atsushi Ohuchi, Tadashi Hase, Takatoshi Murase. Perilla extract improves frequent urination in spontaneously hypertensive rats with enhancement of the urothelial presence and anti-inflammatory effects. International journal of urology : official journal of the Japanese Urological Association. 2018 03; 25(3):298-304. doi: 10.1111/iju.13516. [PMID: 29268303]
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  • Lars Duelund, Arnaud Amiot, Alexandra Fillon, Ole G Mouritsen. Influence of the active compounds of Perilla frutescens leaves on lipid membranes. Journal of natural products. 2012 Feb; 75(2):160-6. doi: 10.1021/np200713q. [PMID: 22272932]
  • Sabita N Saldanha, Trygve O Tollefsbol. The role of nutraceuticals in chemoprevention and chemotherapy and their clinical outcomes. Journal of oncology. 2012; 2012(?):192464. doi: 10.1155/2012/192464. [PMID: 22187555]
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  • Himanshu Khandelia, Sarah Witzke, Ole G Mouritsen. Interaction of salicylate and a terpenoid plant extract with model membranes: reconciling experiments and simulations. Biophysical journal. 2010 Dec; 99(12):3887-94. doi: 10.1016/j.bpj.2010.11.009. [PMID: 21156130]
  • P Pratheeshkumar, T J Raphael, Girija Kuttan. Protective role of perillic acid against radiation-induced oxidative stress, cytokine profile, DNA damage, and intestinal toxicity in mice. Journal of environmental pathology, toxicology and oncology : official organ of the International Society for Environmental Toxicology and Cancer. 2010; 29(3):199-212. doi: 10.1615/jenvironpatholtoxicoloncol.v29.i3.40. [PMID: 21303327]
  • Laxmi Yeruva, Keon J Pierre, Abiodun Elegbede, Robert C Wang, Stephen W Carper. Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells. Cancer letters. 2007 Nov; 257(2):216-26. doi: 10.1016/j.canlet.2007.07.020. [PMID: 17888568]
  • Sota Omoigui. The Interleukin-6 inflammation pathway from cholesterol to aging--role of statins, bisphosphonates and plant polyphenols in aging and age-related diseases. Immunity & ageing : I & A. 2007 Mar; 4(?):1. doi: 10.1186/1742-4933-4-1. [PMID: 17374166]
  • Mercedes Montiel, Enrique Pérez de la Blanca, Eugenio Jiménez. P2Y receptors activate MAPK/ERK through a pathway involving PI3K/PDK1/PKC-zeta in human vein endothelial cells. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2006; 18(1-3):123-34. doi: 10.1159/000095180. [PMID: 16914897]
  • Howard H Bailey, George Wilding, Kendra D Tutsch, Rhoda Z Arzoomanian, Dona Alberti, Chris Feierabend, Kris Simon, Rebecca Marnocha, Sarah A Holstein, Jan Stewart, Kriste A Lewis, Raymond J Hohl. A phase I trial of perillyl alcohol administered four times daily for 14 days out of 28 days. Cancer chemotherapy and pharmacology. 2004 Oct; 54(4):368-76. doi: 10.1007/s00280-004-0788-z. [PMID: 15205914]
  • Darrin M Beaupre, Jennifer McCafferty-Grad, Nizar J Bahlis, Lawrence H Boise, Mathias G Lichtenheld. Farnesyl transferase inhibitors enhance death receptor signals and induce apoptosis in multiple myeloma cells. Leukemia & lymphoma. 2003 Dec; 44(12):2123-34. doi: 10.1080/1042819031000116652. [PMID: 14959858]
  • T J Raphael, G Kuttan. Effect of naturally occurring monoterpenes carvone, limonene and perillic acid in the inhibition of experimental lung metastasis induced by B16F-10 melanoma cells. Journal of experimental & clinical cancer research : CR. 2003 Sep; 22(3):419-24. doi: . [PMID: 14582701]
  • Christopher G Azzoli, Vincent A Miller, Kenneth K Ng, Lee M Krug, David R Spriggs, William P Tong, Elyn R Riedel, Mark G Kris. A phase I trial of perillyl alcohol in patients with advanced solid tumors. Cancer chemotherapy and pharmacology. 2003 Jun; 51(6):493-8. doi: 10.1007/s00280-003-0599-7. [PMID: 12695855]
  • Sarah A Holstein, Raymond J Hohl. Monoterpene regulation of Ras and Ras-related protein expression. Journal of lipid research. 2003 Jun; 44(6):1209-15. doi: 10.1194/jlr.m300057-jlr200. [PMID: 12671036]
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