Tropoflavin (BioDeep_00000000154)

Main id: BioDeep_00000277124

 

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


7,8-dihydroxy-2-phenyl-chromen-4-one;7,8-Dihydroxyflavone

化学式: C15H10O4 (254.0579)
中文名称: 7,8-二羟基黄酮水合物, 7,8-二羟基黄酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O
InChI: InChI=1S/C15H10O4/c16-11-7-6-10-12(17)8-13(19-15(10)14(11)18)9-4-2-1-3-5-9/h1-8,16,18H

描述信息

7,8-dihydroxyflavone is a dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A naturally occurring flavonoid produced by several plants, including the weed Tridax procumbens (coalbuttons or tridax daisy) and the tree Godmania aesculifolia, In animal models, it has shown efficacy against several diseases of the nervous system, including Alzheimers, Parkinsons, and Huntingtons. It has a role as a plant metabolite, a tropomyosin-related kinase B receptor agonist, an antidepressant, an antioxidant and an antineoplastic agent.
A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A naturally occurring flavonoid produced by several plants, including the weed Tridax procumbens (coalbuttons or tridax daisy) and the tree Godmania aesculifolia, In animal models, it has shown efficacy against several diseases of the nervous system, including Alzheimers, Parkinsons, and Huntingtons.
7,8-Dihydroxyflavone is a potent and selective TrkB agonist that mimics the physiological actions of Brain-derived neurotrophic factor (BDNF). Displays therapeutic efficacy toward various neurological diseases[1].
7,8-Dihydroxyflavone is a potent and selective TrkB agonist that mimics the physiological actions of Brain-derived neurotrophic factor (BDNF). Displays therapeutic efficacy toward various neurological diseases[1].

同义名列表

35 个代谢物同义名

7,8-dihydroxy-2-phenyl-chromen-4-one;7,8-Dihydroxyflavone; 2(1H)-Pentalenone, 4,5,6,6a-tetrahydro-1,3-dimethyl-; 4H-1-Benzopyran-4-one, 7,8-dihydroxy-2-phenyl-; 4H-1-Benzopyran-4-one,7,8-dihydroxy-2-phenyl-; 5-18-04-00079 (Beilstein Handbook Reference); 7,8-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one; 7,8-Dihydroxyflavone hydrate, >=98\\% (HPLC); 7,8-dihydroxy-2-phenyl-4H-chromen-4-one; 7,8-Dihydroxy-2-phenyl-4-benzopyrone; 7,8-Dihydroxy-2-phenyl-chromen-4-one; 7,8-dihydroxy-2-phenylchromen-4-one; 7,8-dihydroxy-2-phenylchromone; 7,8-Dihydroxyflavone hydrate; 7,8-Dihydroxy-flavone; 7,8-Dihydroxyflavone; 6,7-dihydroxyflavone; Spectrum4_001823; Spectrum2_000952; Spectrum3_000213; Spectrum5_000585; 7,8-diOH-Flavone; UNII-ADB6MA8ZV2; MEGxp0_001683; DivK1c_000371; KBio2_004135; Tox21_501075; KBio2_006703; KBio3_001325; KBio2_001567; KBio1_000371; IDI1_000371; ADB6MA8ZV2; DHF, 7,8-; 7,8-DHF; 8-DHF



数据库引用编号

12 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)

3 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 14 BCL2, BDNF, CA1, CA3, CAT, IGHMBP2, MAPK14, NFE2L2, NOS2, NTRK2, PIK3CA, PRKAA2, SNCA, TNK1
Peripheral membrane protein 1 TNK1
Endosome membrane 1 NTRK2
Endoplasmic reticulum membrane 3 BCL2, GRIA1, HMOX1
Nucleus 9 BCL2, HMOX1, IGHMBP2, MAPK14, NFE2L2, NOS2, PPARGC1A, PRKAA2, SNCA
cytosol 14 BCL2, CA1, CA3, CAT, GRIA1, HMOX1, MAPK14, NFE2L2, NOS2, NTRK2, PIK3CA, PPARGC1A, PRKAA2, SNCA
dendrite 4 BDNF, GRIA1, NTRK2, PRKAA2
nuclear body 1 IGHMBP2
centrosome 1 NFE2L2
nucleoplasm 7 HMOX1, IGHMBP2, MAPK14, NFE2L2, NOS2, PPARGC1A, PRKAA2
RNA polymerase II transcription regulator complex 1 NFE2L2
Cell membrane 3 GRIA1, NTRK2, TNF
Cytoplasmic side 1 HMOX1
lamellipodium 1 PIK3CA
Cell projection, axon 3 IGHMBP2, NTRK2, SNCA
Early endosome membrane 2 GRIA1, NTRK2
Multi-pass membrane protein 1 GRIA1
Synapse 2 GRIA1, SNCA
cell cortex 1 SNCA
cell surface 2 GRIA1, TNF
dendritic shaft 1 GRIA1
glutamatergic synapse 2 GRIA1, MAPK14
Golgi apparatus 2 NFE2L2, PRKAA2
Golgi membrane 1 INS
growth cone 2 IGHMBP2, SNCA
neuromuscular junction 1 GRIA1
neuronal cell body 4 GRIA1, PRKAA2, SNCA, TNF
postsynapse 1 SNCA
synaptic vesicle 1 BDNF
Cytoplasm, cytosol 2 NFE2L2, NOS2
Lysosome 1 SNCA
Presynapse 1 GRIA1
plasma membrane 8 GRIA1, NFE2L2, NOS2, NTRK2, PIK3CA, SNCA, TNF, TNK1
synaptic vesicle membrane 2 GRIA1, SNCA
terminal bouton 1 NTRK2
Membrane 10 BCL2, BDNF, CAT, GRIA1, HMOX1, IGHMBP2, NTRK2, PRKAA2, SNCA, TNK1
axon 5 BDNF, IGHMBP2, NTRK2, PRKAA2, SNCA
extracellular exosome 2 CA1, CAT
endoplasmic reticulum 2 BCL2, HMOX1
extracellular space 6 BDNF, HMOX1, IL6, INS, SNCA, TNF
perinuclear region of cytoplasm 6 BDNF, HMOX1, NOS2, NTRK2, PIK3CA, SNCA
intercalated disc 1 PIK3CA
mitochondrion 4 BCL2, CAT, MAPK14, SNCA
protein-containing complex 3 BCL2, CAT, SNCA
intracellular membrane-bounded organelle 1 CAT
postsynaptic density 2 GRIA1, NTRK2
Single-pass type I membrane protein 1 NTRK2
Secreted 4 BDNF, IL6, INS, SNCA
extracellular region 7 BDNF, CAT, IL6, INS, MAPK14, SNCA, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, HMOX1
excitatory synapse 1 GRIA1
neuronal cell body membrane 1 GRIA1
mitochondrial matrix 1 CAT
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 GRIA1, TNF
actin cytoskeleton 1 SNCA
dendritic spine 2 GRIA1, NTRK2
neuron spine 1 GRIA1
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
Early endosome 1 NTRK2
cell-cell junction 1 GRIA1
recycling endosome 2 GRIA1, TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 GRIA1
presynaptic active zone membrane 1 GRIA1
Cytoplasm, perinuclear region 2 NOS2, NTRK2
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 CAT
Peroxisome 2 CAT, NOS2
Peroxisome matrix 1 CAT
peroxisomal matrix 2 CAT, NOS2
peroxisomal membrane 1 CAT
Cell projection, dendritic spine 1 GRIA1
Nucleus, PML body 1 PPARGC1A
PML body 1 PPARGC1A
nuclear speck 2 MAPK14, PRKAA2
Postsynaptic cell membrane 1 GRIA1
receptor complex 1 NTRK2
chromatin 2 NFE2L2, PPARGC1A
mediator complex 1 NFE2L2
phagocytic cup 1 TNF
supramolecular fiber 1 SNCA
spindle pole 1 MAPK14
postsynaptic density, intracellular component 1 GRIA1
Recycling endosome membrane 1 GRIA1
endosome lumen 1 INS
AMPA glutamate receptor complex 1 GRIA1
Cell projection, dendrite 2 GRIA1, NTRK2
cytoplasmic stress granule 1 PRKAA2
myelin sheath 1 BCL2
synaptic membrane 1 GRIA1
ficolin-1-rich granule lumen 2 CAT, MAPK14
secretory granule lumen 3 CAT, INS, MAPK14
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 BDNF, IL6, INS
axon terminus 2 NTRK2, SNCA
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
endocytic vesicle membrane 1 GRIA1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GRIA1, INS
postsynaptic density membrane 1 GRIA1
Single-pass type IV membrane protein 1 HMOX1
ER to Golgi transport vesicle membrane 1 GRIA1
ribonucleoprotein complex 1 IGHMBP2
[Isoform 1]: Nucleus 1 PPARGC1A
protein-DNA complex 1 NFE2L2
nucleotide-activated protein kinase complex 1 PRKAA2
dendritic spine membrane 1 GRIA1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cortical cytoskeleton 1 NOS2
catalase complex 1 CAT
inclusion body 1 SNCA
interleukin-6 receptor complex 1 IL6
BAD-BCL-2 complex 1 BCL2
proximal dendrite 1 GRIA1
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
axonal spine 1 GRIA1
perisynaptic space 1 GRIA1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[Isoform B4]: Nucleus 1 PPARGC1A
[Isoform B4-8a]: Cytoplasm 1 PPARGC1A
[Isoform B5]: Nucleus 1 PPARGC1A
[Isoform 9]: Nucleus 1 PPARGC1A


文献列表

  • Man-Ru Zhang, Bang-Yun Zuo, Yu-Chen Song, Dan-Dan Guo, Qing-Liu Li, Jin-Xiu Lyu, Hua Zhu, Jing Zhao, Peng-Zhou Hang. BDNF mimetics recover palmitic acid-induced injury in cardiomyocytes by ameliorating Akt-dependent mitochondrial impairments. Toxicology and applied pharmacology. 2024 May; 486(?):116951. doi: 10.1016/j.taap.2024.116951. [PMID: 38705401]
  • Ying Xu, Xueting Wang, Ziyang Xu, Fengwei Sun, Yue Tian. Tbx2 Knockdown alleviated sevoflurane-induced cognitive disorder and neuron damages in aged rats via suppressing oxidative stress and ferroptosis. Toxicological sciences : an official journal of the Society of Toxicology. 2023 Jul; ?(?):. doi: 10.1093/toxsci/kfad071. [PMID: 37494465]
  • Kaimei Lu, Liyan Zhao, Yonghai Zhang, Fan Yang, Huiwen Zhang, Jie Wang, Bin Li, Guimei Ji, Jianqiang Yu, Hanxiang Ma. Bupivacaine reduces GlyT1 expression by potentiating the p-AMPKα/BDNF signalling pathway in spinal astrocytes of rats. Scientific reports. 2022 01; 12(1):1378. doi: 10.1038/s41598-022-05478-3. [PMID: 35082359]
  • Rajib Paul, Joyobrato Nath, Satinath Paul, Muhammed Khairujjaman Mazumder, Banashree Chetia Phukan, Rubina Roy, Pallab Bhattacharya, Anupom Borah. Suggesting 7,8-dihydroxyflavone as a promising nutraceutical against CNS disorders. Neurochemistry international. 2021 09; 148(?):105068. doi: 10.1016/j.neuint.2021.105068. [PMID: 34022252]
  • Fan Xue, Zhenlei Zhao, Yanpei Gu, Jianxin Han, Keqiang Ye, Ying Zhang. 7,8-Dihydroxyflavone modulates bone formation and resorption and ameliorates ovariectomy-induced osteoporosis. eLife. 2021 07; 10(?):. doi: 10.7554/elife.64872. [PMID: 34227467]
  • Ansab Akhtar, Jatinder Dhaliwal, Sangeeta Pilkhwal Sah. 7,8-Dihydroxyflavone improves cognitive functions in ICV-STZ rat model of sporadic Alzheimer's disease by reversing oxidative stress, mitochondrial dysfunction, and insulin resistance. Psychopharmacology. 2021 Jul; 238(7):1991-2009. doi: 10.1007/s00213-021-05826-7. [PMID: 33774703]
  • 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]
  • Sarah Ötzkan, Walter E Muller, W Gibson Wood, Gunter P Eckert. Effects of 7,8-Dihydroxyflavone on Lipid Isoprenoid and Rho Protein Levels in Brains of Aged C57BL/6 Mice. Neuromolecular medicine. 2021 03; 23(1):130-139. doi: 10.1007/s12017-020-08640-0. [PMID: 33377988]
  • Zhenlei Zhao, Fan Xue, Yanpei Gu, Jianxin Han, Yingxian Jia, Keqiang Ye, Ying Zhang. Crosstalk between the muscular estrogen receptor α and BDNF/TrkB signaling alleviates metabolic syndrome via 7,8-dihydroxyflavone in female mice. Molecular metabolism. 2021 03; 45(?):101149. doi: 10.1016/j.molmet.2020.101149. [PMID: 33352311]
  • Priyanka Sharma, Guojun Wu, Deeptha Kumaraswamy, Natalie Burchat, Hong Ye, Yongjia Gong, Liping Zhao, Yan Y Lam, Harini Sampath. Sex-Dependent Effects of 7,8-Dihydroxyflavone on Metabolic Health Are Associated with Alterations in the Host Gut Microbiome. Nutrients. 2021 Feb; 13(2):. doi: 10.3390/nu13020637. [PMID: 33669347]
  • Ismail S Zaitoun, Yong-Seok Song, Andrew Suscha, Mohamed El Ragaby, Christine M Sorenson, Nader Sheibani. 7, 8-Dihydroxyflavone, a TrkB receptor agonist, provides minimal protection against retinal vascular damage during oxygen-induced ischemic retinopathy. PloS one. 2021; 16(12):e0260793. doi: 10.1371/journal.pone.0260793. [PMID: 34855884]
  • Hatice Keser, Şeniz Doğramacı, Elif Şahin, Neslihan Sağlam, Mehmet Erdem, Ahmet Alver, Selcen Aydin-Abidin. The TrkB agonist 7,8-dihydroxyflavone improves sensory-motor performance and reduces lipid peroxidation in old mice. General physiology and biophysics. 2020 Sep; 39(5):471-479. doi: 10.4149/gpb_2020022. [PMID: 33084600]
  • Nashwa Amin, Shiyi Xie, Xiaoning Tan, Yili Chen, Qiannan Ren, Benson O A Botchway, Shaohua Hu, Yongchun Ma, Zhiying Hu, Marong Fang. Optimized integration of fluoxetine and 7, 8-dihydroxyflavone as an efficient therapy for reversing depressive-like behavior in mice during the perimenopausal period. Progress in neuro-psychopharmacology & biological psychiatry. 2020 07; 101(?):109939. doi: 10.1016/j.pnpbp.2020.109939. [PMID: 32243998]
  • Dinesh Kumar, Durgesh Kumar Dwivedi, Mangala Lahkar, Ashok Jangra. Hepatoprotective potential of 7,8-Dihydroxyflavone against alcohol and high-fat diet induced liver toxicity via attenuation of oxido-nitrosative stress and NF-κB activation. Pharmacological reports : PR. 2019 Dec; 71(6):1235-1243. doi: 10.1016/j.pharep.2019.07.002. [PMID: 31670060]
  • Eszter Fliszár-Nyúl, Violetta Mohos, Tímea Bencsik, Beáta Lemli, Sándor Kunsági-Máté, Miklós Poór. Interactions of 7,8-Dihydroxyflavone with Serum Albumin as well as with CYP2C9, CYP2C19, CYP3A4, and Xanthine Oxidase Biotransformation Enzymes. Biomolecules. 2019 10; 9(11):. doi: 10.3390/biom9110655. [PMID: 31731555]
  • John Wood, Margaret Chui Ling Tse, Xiuying Yang, Daniel Brobst, Zhixue Liu, Brian Pak Shing Pang, Wing Suen Chan, Aung Moe Zaw, Billy K C Chow, Keqiang Ye, Chi Wai Lee, Chi Bun Chan. BDNF mimetic alleviates body weight gain in obese mice by enhancing mitochondrial biogenesis in skeletal muscle. Metabolism: clinical and experimental. 2018 10; 87(?):113-122. doi: 10.1016/j.metabol.2018.06.007. [PMID: 29935237]
  • Min-Wang Zhang, She-Feng Zhang, Zhen-Hua Li, Fang Han. 7,8-Dihydroxyflavone reverses the depressive symptoms in mouse chronic mild stress. Neuroscience letters. 2016 Dec; 635(?):33-38. doi: 10.1016/j.neulet.2016.10.035. [PMID: 27773794]
  • Ji Won Choi, Chang Won Lee, Jisun Lee, Doo Jin Choi, Jae Kyung Sohng, Yong Il Park. 7,8-Dihydroxyflavone inhibits adipocyte differentiation via antioxidant activity and induces apoptosis in 3T3-L1 preadipocyte cells. Life sciences. 2016 Jan; 144(?):103-12. doi: 10.1016/j.lfs.2015.11.028. [PMID: 26631505]
  • Qian Ren, Ji-Chun Zhang, Min Ma, Yuko Fujita, Jin Wu, Kenji Hashimoto. 7,8-Dihydroxyflavone, a TrkB agonist, attenuates behavioral abnormalities and neurotoxicity in mice after administration of methamphetamine. Psychopharmacology. 2014 Jan; 231(1):159-66. doi: 10.1007/s00213-013-3221-7. [PMID: 23934209]
  • Vadim Bernard-Gauthier, Mehdi Boudjemeline, Pedro Rosa-Neto, Alexander Thiel, Ralf Schirrmacher. Towards tropomyosin-related kinase B (TrkB) receptor ligands for brain imaging with PET: radiosynthesis and evaluation of 2-(4-[(18)F]fluorophenyl)-7,8-dihydroxy-4H-chromen-4-one and 2-(4-([N-methyl-(11)C]-dimethylamino)phenyl)-7,8-dihydroxy-4H-chromen-4-one. Bioorganic & medicinal chemistry. 2013 Dec; 21(24):7816-29. doi: 10.1016/j.bmc.2013.10.012. [PMID: 24183588]
  • Aurélie Blugeot, Cyril Rivat, Elodie Bouvier, Jenny Molet, Amandine Mouchard, Brigitte Zeau, Christophe Bernard, Jean-Jacques Benoliel, Chrystel Becker. Vulnerability to depression: from brain neuroplasticity to identification of biomarkers. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2011 Sep; 31(36):12889-99. doi: 10.1523/jneurosci.1309-11.2011. [PMID: 21900567]
  • K Kozics, Z Valovicova, D Slamenova. Structure of flavonoids influences the degree inhibition of Benzo(a)pyrene - induced DNA damage and micronuclei in HepG2 cells. Neoplasma. 2011; 58(6):516-24. doi: 10.4149/neo_2011_06_516. [PMID: 21895405]
  • Cristina Muñoz-Abellán, Cristina Rabasa, Nuria Daviu, Roser Nadal, Antonio Armario. Behavioral and endocrine consequences of simultaneous exposure to two different stressors in rats: interaction or independence?. PloS one. 2011; 6(6):e21426. doi: 10.1371/journal.pone.0021426. [PMID: 21731743]
  • Yunbao Liu, Muraleedharan G Nair. An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds. Journal of natural products. 2010 Jul; 73(7):1193-5. doi: 10.1021/np1000945. [PMID: 20565070]
  • J Zhao, P Mak, A Tchoudakova, G Callard, S Chen. Different catalytic properties and inhibitor responses of the goldfish brain and ovary aromatase isozymes. General and comparative endocrinology. 2001 Aug; 123(2):180-91. doi: 10.1006/gcen.2001.7661. [PMID: 11482939]
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  • C Q Hu, K Chen, Q Shi, R E Kilkuskie, Y C Cheng, K H Lee. Anti-AIDS agents, 10. Acacetin-7-O-beta-D-galactopyranoside, an anti-HIV principle from Chrysanthemum morifolium and a structure-activity correlation with some related flavonoids. Journal of natural products. 1994 Jan; 57(1):42-51. doi: 10.1021/np50103a006. [PMID: 8158164]