Tropolone (BioDeep_00000010734)

 

Secondary id: BioDeep_00000396908

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


2-Hydroxy-2,4,6-cycloheptatrien-1-one

化学式: C7H6O2 (122.0368)
中文名称: 环庚三烯酚酮
谱图信息: 最多检出来源 Homo sapiens(blood) 57.58%

分子结构信息

SMILES: C1=CC=C(C(=O)C=C1)O
InChI: InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)

描述信息

Tropolone, a ?tropone derivative with a?hydroxyl group?in the 2-position, is a precursor?of manyazulene derivatives such as?methyl 2-methylazulene-1-carboxylate[1]. Tropolone is a potent inhibitor of mushroom tyrosinase with a IC50 of 0.4 μM, and the inhibition can be reversed by dialysis or by excess CU2+[2].

同义名列表

8 个代谢物同义名

2-Hydroxy-2,4,6-cycloheptatrien-1-one; 2-hydroxycyclohepta-2,4,6-trien-1-one; 2-Hydroxycyclohepta-2,4,6-trienone; 2-Hydroxytropone; Purpurocatechol; Tropolone; Tropolone; Tropolone



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(6)

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)

2 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 10 CASP3, CAT, DNM2, GSN, MYLK, PMP2, TMOD3, TPM4, TUBB4B, TYR
Peripheral membrane protein 1 DNM2
Endosome membrane 1 TF
Nucleus 3 CASP3, PMP2, TUBB4B
cytosol 13 CASP3, CAT, COMT, DNM2, GSN, MYLK, PMP2, TMOD1, TPM1, TPM2, TPM3, TPM4, TUBB4B
dendrite 1 COMT
phagocytic vesicle 1 GSN
centrosome 1 DNM2
nucleoplasm 2 ATP2B1, CASP3
Cell membrane 3 ATP2B1, COMT, TNF
Cleavage furrow 1 MYLK
lamellipodium 2 GSN, MYLK
ruffle membrane 1 TPM1
Multi-pass membrane protein 1 ATP2B1
Synapse 4 ATP2B1, COMT, DNM2, MYLK
cell junction 1 DNM2
cell surface 2 TF, TNF
glutamatergic synapse 2 ATP2B1, CASP3
Golgi apparatus 1 DNM2
Golgi membrane 1 DNM2
neuronal cell body 2 CASP3, TNF
presynaptic membrane 1 ATP2B1
Lysosome 1 TYR
Presynapse 1 DNM2
endosome 1 DNM2
plasma membrane 8 ATP2B1, COMT, DNM2, GSN, IGHE, MYLK, TF, TNF
synaptic vesicle membrane 1 ATP2B1
Membrane 6 ATP2B1, CAT, COMT, TMOD1, TPM1, TPM4
apical plasma membrane 1 TF
axon 1 COMT
basolateral plasma membrane 1 ATP2B1
extracellular exosome 11 ATP2B1, CAT, COMT, CPVL, DNM2, GSN, PMP2, TF, TPM3, TPM4, TUBB4B
extracellular space 4 GSN, IGHE, TF, TNF
perinuclear region of cytoplasm 2 TF, TYR
adherens junction 1 TMOD3
mitochondrion 2 CAT, TPM3
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 4 ATP2B1, CAT, COMT, TYR
postsynaptic density 2 CASP3, DNM2
Single-pass type I membrane protein 2 IGHE, TYR
Secreted 1 TF
extracellular region 6 CAT, GSN, IGHE, TF, TNF, TUBB4B
basal part of cell 1 TF
mitochondrial matrix 1 CAT
Extracellular side 1 COMT
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 DNM2
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
external side of plasma membrane 1 TNF
Extracellular vesicle 1 TUBB4B
actin cytoskeleton 5 GSN, MYLK, TPM1, TPM2, TPM3
cytoplasmic vesicle 1 TF
microtubule cytoskeleton 1 TUBB4B
Melanosome membrane 1 TYR
midbody 1 DNM2
sarcoplasm 1 GSN
Early endosome 1 TF
Membrane, clathrin-coated pit 1 DNM2
clathrin-coated pit 2 DNM2, TF
Golgi-associated vesicle 1 TYR
recycling endosome 3 DNM2, TF, TNF
Single-pass type II membrane protein 2 COMT, TNF
vesicle 1 TF
postsynaptic membrane 1 DNM2
Cell projection, lamellipodium 1 MYLK
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 9 DNM2, GSN, TMOD1, TMOD3, TPM1, TPM2, TPM3, TPM4, TUBB4B
focal adhesion 4 CAT, DNM2, GSN, TPM4
microtubule 2 DNM2, TUBB4B
Peroxisome 1 CAT
myofibril 2 TMOD1, TMOD3
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
lateral plasma membrane 1 ATP2B1
Late endosome 1 TF
sarcomere 2 TMOD1, TPM1
neuron projection 1 DNM2
IgE immunoglobulin complex 1 IGHE
Cytoplasmic vesicle, phagosome membrane 1 DNM2
Cell projection, phagocytic cup 1 DNM2
cell projection 1 ATP2B1
phagocytic cup 2 DNM2, TNF
phagocytic vesicle membrane 1 DNM2
mitotic spindle 1 TUBB4B
cytoskeleton 8 GSN, TMOD1, TMOD3, TPM1, TPM2, TPM3, TPM4, TUBB4B
Cell projection, podosome 1 DNM2
podosome 3 DNM2, GSN, TPM4
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome, centriole 1 DNM2
centriole 1 DNM2
actin filament 5 TMOD1, TPM1, TPM2, TPM3, TPM4
blood microparticle 2 GSN, TF
Basolateral cell membrane 1 ATP2B1
[Isoform 2]: Cell membrane 1 IGHE
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
axonemal microtubule 1 TUBB4B
Melanosome 1 TYR
Presynaptic cell membrane 1 ATP2B1
myelin sheath 1 PMP2
stress fiber 4 MYLK, TPM1, TPM3, TPM4
basal plasma membrane 1 TF
clathrin-coated vesicle 1 DNM2
ficolin-1-rich granule lumen 2 CAT, GSN
secretory granule lumen 3 CAT, GSN, TF
HFE-transferrin receptor complex 1 TF
endoplasmic reticulum lumen 1 TF
cortical actin cytoskeleton 1 GSN
actin cap 1 GSN
endocytic vesicle membrane 1 DNM2
Cytoplasmic vesicle, clathrin-coated vesicle 1 DNM2
endocytic vesicle 1 TF
azurophil granule lumen 1 TUBB4B
immunological synapse 1 ATP2B1
clathrin-coated endocytic vesicle membrane 1 TF
Cytoplasm, cytoskeleton, stress fiber 1 MYLK
uropod 1 DNM2
Synapse, synaptosome 1 DNM2
death-inducing signaling complex 1 CASP3
Cell projection, uropodium 1 DNM2
[Isoform 3]: Cell membrane 1 IGHE
vesicle coat 1 TF
bleb 1 TPM1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
cortical cytoskeleton 2 TMOD1, TPM4
catalase complex 1 CAT
muscle thin filament tropomyosin 4 TPM1, TPM2, TPM3, TPM4
photoreceptor ribbon synapse 1 ATP2B1
[Isoform Soluble]: Cytoplasm 1 COMT
[Isoform Membrane-bound]: Cell membrane 1 COMT
striated muscle thin filament 2 TMOD1, TMOD3
dense body 1 TF
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yue Jin, Zongxin Guo, Huilin Zhu, Zixuan Zhang, Xiaowen Jiang, Yiren Yang, Pengyu Liu, Yu Yang, Miao Wang, Huiyuan Gao. Discovery of potential components characteristic by conjugated enone from the branches and leaves of Croton lauioides with anti-neuroinflammatory activity via regulating the NF-κB pathway. Bioorganic chemistry. 2024 May; 146(?):107301. doi: 10.1016/j.bioorg.2024.107301. [PMID: 38522392]
  • Sylwia Jafra, Magdalena Jabłońska, Tomasz Maciąg, Marta Matuszewska, Marcin Borowicz, Michał Prusiński, Wioletta Żmudzińska, Marcel Thiel, Paulina Czaplewska, Dorota M Krzyżanowska, Robert Czajkowski. An iron fist in a velvet glove: The cooperation of a novel pyoverdine from Pseudomonas donghuensis P482 with 7-hydroxytropolone is pivotal for its antibacterial activity. Environmental microbiology. 2024 Jan; 26(1):e16559. doi: 10.1111/1462-2920.16559. [PMID: 38151794]
  • Hongxing Tang, Kejun He, Kun Zhao, Chen Zheng, Weichi Wu, Weilin Jin, Lixuan Yang, Baoshu Xie. Protective effects of Hinokitiol on neuronal ferroptosis by activating the KEAP1/NRF-2/HO-1 pathway in traumatic brain injury. Journal of neurotrauma. 2023 Nov; ?(?):. doi: 10.1089/neu.2023.0150. [PMID: 37962273]
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  • Yamini Chelpuri, Shivakumar Pabbathi, Gopala Reddy Alla, Ravi Kumar Yadala, Mounika Kamishetti, Anil Kumar Banothu, Ramya Boinepally, Kala Kumar Bharani, Amit Khurana. Tropolone derivative hinokitiol ameliorates cerulein-induced acute pancreatitis in mice. International immunopharmacology. 2022 Aug; 109(?):108915. doi: 10.1016/j.intimp.2022.108915. [PMID: 35679663]
  • Biao Wang, Bo He, Tianyu Chen, Hao Li, Liyifan Chen, Yiliang Chen, Kailin Tian, Kun Yang, Danyu Shen, Wei Yan, Yonghao Ye. Discovery of Tropolone Stipitaldehyde as a Potential Agent for Controlling Phytophthora Blight and Its Action Mechanism Research. Journal of agricultural and food chemistry. 2022 Jul; 70(28):8693-8703. doi: 10.1021/acs.jafc.2c03163. [PMID: 35793537]
  • Xuan Tao, Lu Zhang, Liubing Du, Kai Lu, Zhennan Zhao, Yanxuan Xie, Xiaobo Li, Shuxiang Huang, Pei-Hui Wang, Ji-An Pan, Wei Xia, Jun Dai, Zong-Wan Mao. Inhibition of SARS-CoV-2 replication by zinc gluconate in combination with hinokitiol. Journal of inorganic biochemistry. 2022 06; 231(?):111777. doi: 10.1016/j.jinorgbio.2022.111777. [PMID: 35255411]
  • Christopher DeLaney, Yan Sheng, D Chase Pectol, Erol Vantansever, Hanyuan Zhang, Nattamai Bhuvanesh, Isaiah Salas, Wenshe R Liu, Carol F Fierke, Marcetta Y Darensbourg. Zinc thiotropolone combinations as inhibitors of the SARS-CoV-2 main protease. Dalton transactions (Cambridge, England : 2003). 2021 Sep; 50(35):12226-12233. doi: 10.1039/d1dt02499j. [PMID: 34396374]
  • Jae Sung Park, Keebeom Ko, Seong-Hwan Kim, Jae Kyun Lee, Jin-Soo Park, Keunwan Park, Mi Ri Kim, Kyungsu Kang, Dong-Chan Oh, Sun Yeou Kim, Silvia Yumnam, Hak Cheol Kwon, Jongheon Shin. Tropolone-Bearing Sesquiterpenes from Juniperus chinensis: Structures, Photochemistry and Bioactivity. Journal of natural products. 2021 07; 84(7):2020-2027. doi: 10.1021/acs.jnatprod.1c00321. [PMID: 34236881]
  • Ge Zou, Qi Tan, Yan Chen, Wencong Yang, Zhenming Zang, Hongming Jiang, Shenyu Chen, Bo Wang, Zhigang She. Furobenzotropolones A, B and 3-Hydroxyepicoccone B with Antioxidative Activity from Mangrove Endophytic Fungus Epicoccum nigrum MLY-3. Marine drugs. 2021 Jul; 19(7):. doi: 10.3390/md19070395. [PMID: 34356820]
  • Marketa Houdkova, Aishwarya Chaure, Ivo Doskocil, Jaroslav Havlik, Ladislav Kokoska. New Broth Macrodilution Volatilization Method for Antibacterial Susceptibility Testing of Volatile Agents and Evaluation of Their Toxicity Using Modified MTT Assay In Vitro. Molecules (Basel, Switzerland). 2021 Jul; 26(14):. doi: 10.3390/molecules26144179. [PMID: 34299454]
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  • Saideng Lu, Yu Song, Rongjin Luo, Shuai Li, Gaocai Li, Kun Wang, Zhiwei Liao, Bingjin Wang, Wencan Ke, Qian Xiang, Chao Chen, Xinghuo Wu, Yukun Zhang, Li Ling, Cao Yang. Ferroportin-Dependent Iron Homeostasis Protects against Oxidative Stress-Induced Nucleus Pulposus Cell Ferroptosis and Ameliorates Intervertebral Disc Degeneration In Vivo. Oxidative medicine and cellular longevity. 2021; 2021(?):6670497. doi: 10.1155/2021/6670497. [PMID: 33628376]
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  • Qin-Ge Ma, Rong-Rui Wei, Xiao-Dong Zhang, Zhi-Pei Sang, Jiang-Hong Dong, Qi-Xin Lu, Hao-Feng Huang, Dong-Mei Guo, Lin Jiang. Tropolone derivatives with hepatoprotective and antiproliferative activities from the aerial parts of Chenopodium album Linn. Fitoterapia. 2020 Oct; 146(?):104733. doi: 10.1016/j.fitote.2020.104733. [PMID: 32979464]
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  • Jungwook Park, Hyun-Hee Lee, Hyejung Jung, Young-Su Seo. Transcriptome analysis to understand the effects of the toxoflavin and tropolone produced by phytopathogenic Burkholderia on Escherichia coli. Journal of microbiology (Seoul, Korea). 2019 Sep; 57(9):781-794. doi: 10.1007/s12275-019-9330-1. [PMID: 31452043]
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  • Nobuya Magori, Tsugumi Fujita, Eiichi Kumamoto. Hinokitiol inhibits compound action potentials in the frog sciatic nerve. European journal of pharmacology. 2018 Jan; 819(?):254-260. doi: 10.1016/j.ejphar.2017.12.014. [PMID: 29225186]
  • Lihong Zhang, Yang Peng, Ivan P Uray, Jianfeng Shen, Lulu Wang, Xiangdong Peng, Powel H Brown, Wei Tu, Guang Peng. Natural product β-thujaplicin inhibits homologous recombination repair and sensitizes cancer cells to radiation therapy. DNA repair. 2017 12; 60(?):89-101. doi: 10.1016/j.dnarep.2017.10.009. [PMID: 29112893]
  • Eva Christina Sonnenschein, Christopher Broughton William Phippen, Kristian Fog Nielsen, Ramona Valentina Mateiu, Jette Melchiorsen, Lone Gram, Jörg Overmann, Heike M Freese. Phaeobacter piscinae sp. nov., a species of the Roseobacter group and potential aquaculture probiont. International journal of systematic and evolutionary microbiology. 2017 Nov; 67(11):4559-4564. doi: 10.1099/ijsem.0.002331. [PMID: 28984543]
  • Ammar Kurdi, Matthias Cleenewerck, Christel Vangestel, Sophie Lyssens, Wim Declercq, Jean-Pierre Timmermans, Sigrid Stroobants, Koen Augustyns, Guido R Y De Meyer, Pieter Van Der Veken, Wim Martinet. ATG4B inhibitors with a benzotropolone core structure block autophagy and augment efficiency of chemotherapy in mice. Biochemical pharmacology. 2017 08; 138(?):150-162. doi: 10.1016/j.bcp.2017.06.119. [PMID: 28642033]
  • Huijuan Guo, René Benndorf, Daniel Leichnitz, Jonathan L Klassen, John Vollmers, Helmar Görls, Matthias Steinacker, Christiane Weigel, Hans-Martin Dahse, Anne-Kristin Kaster, Z Wilhelm de Beer, Michael Poulsen, Christine Beemelmanns. Isolation, Biosynthesis and Chemical Modifications of Rubterolones A-F: Rare Tropolone Alkaloids from Actinomadura sp. 5-2. Chemistry (Weinheim an der Bergstrasse, Germany). 2017 Jul; 23(39):9338-9345. doi: 10.1002/chem.201701005. [PMID: 28463423]
  • Beulaja Manikandan, Manikandan Ramar, Thiagarajan Raman, Mullainadhan Periasamy, Arumugam Munusamy. Purification and characterisation of a pronase-inducible lectin isolated from human serum. International journal of biological macromolecules. 2017 Jun; 99(?):443-453. doi: 10.1016/j.ijbiomac.2017.02.022. [PMID: 28212932]
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  • Koki Fujita, Ryo Kambe, Ransika De Alwis, Tatsuya Yagi, Yuji Tsutsumi. Airborne Monoterpenes Emitted from a Cupressus lusitanica Cell Culture Induce a Signaling Cascade that Produces β-Thujaplicin. Journal of chemical ecology. 2016 Aug; 42(8):814-820. doi: 10.1007/s10886-016-0739-2. [PMID: 27596215]
  • Shunpei Miwa, Eri Kihira, Akinori Yoshioka, Kaoru Nakasone, Sho Okamoto, Masaki Hatano, Masayuki Igarashi, Yoko Eguchi, Akinori Kato, Natsuko Ichikawa, Mitsuo Sekine, Nobuyuki Fujita, Yu Kanesaki, Hirofumi Yoshikawa, Ryutaro Utsumi. Identification of the Three Genes Involved in Controlling Production of a Phytotoxin Tropolone in Burkholderia plantarii. Journal of bacteriology. 2016 06; 198(11):1604-1609. doi: 10.1128/jb.01028-15. [PMID: 27002128]
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