7-Hydroxyflavone (BioDeep_00000002780)

 

Secondary id: BioDeep_00000396900, BioDeep_00000400486

human metabolite PANOMIX_OTCML-2023 Cytotoxicity natural product


代谢物信息卡片


7-Hydroxy-2-phenyl-4-benzopyrone

化学式: C15H10O3 (238.063)
中文名称: 7-羟基黄酮
谱图信息: 最多检出来源 Viridiplantae(plant) 15.23%

分子结构信息

SMILES: c1(ccc2c(c1)oc(cc2=O)c1ccccc1)O
InChI: InChI=1S/C15H10O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-9,16H

描述信息

[Raw Data] CB049_7-Hydroxyflavone_pos_10eV_CB000023.txt
[Raw Data] CB049_7-Hydroxyflavone_pos_30eV_CB000023.txt
[Raw Data] CB049_7-Hydroxyflavone_pos_50eV_CB000023.txt
[Raw Data] CB049_7-Hydroxyflavone_pos_20eV_CB000023.txt
[Raw Data] CB049_7-Hydroxyflavone_pos_40eV_CB000023.txt
[Raw Data] CB049_7-Hydroxyflavone_neg_20eV_000015.txt
[Raw Data] CB049_7-Hydroxyflavone_neg_10eV_000015.txt
[Raw Data] CB049_7-Hydroxyflavone_neg_40eV_000015.txt
[Raw Data] CB049_7-Hydroxyflavone_neg_30eV_000015.txt
[Raw Data] CB049_7-Hydroxyflavone_neg_50eV_000015.txt
7-Hydroxyflavone is a flavonoid isolated from Clerodendrum phlomidis, with anti-inflammatory activity. 7-Hydroxyflavone protects renal cells from nicotine (NIC)-associated cytotoxicity via the ERK/Nrf2/HO-1 pathway[1][2].
7-Hydroxyflavone is a flavonoid isolated from Clerodendrum phlomidis, with anti-inflammatory activity. 7-Hydroxyflavone protects renal cells from nicotine (NIC)-associated cytotoxicity via the ERK/Nrf2/HO-1 pathway[1][2].
7-Hydroxyflavone is a flavonoid isolated from Clerodendrum phlomidis, with anti-inflammatory activity. 7-Hydroxyflavone protects renal cells from nicotine (NIC)-associated cytotoxicity via the ERK/Nrf2/HO-1 pathway[1][2].

同义名列表

3 个代谢物同义名

7-Hydroxy-2-phenyl-4-benzopyrone; 7-Hydroxyflavone; 7-Hydroxyflavone



数据库引用编号

25 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)

25 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 8 AIMP2, ANXA5, BCL2, CYP1A1, FSCN1, KEAP1, MAPK8, PTGS2
Peripheral membrane protein 4 ANXA5, CYP1A1, CYP1B1, PTGS2
Endoplasmic reticulum membrane 8 BCL2, CYP19A1, CYP1A1, CYP1A2, CYP1B1, HMOX1, PTGS2, UGT1A1
Nucleus 6 AIMP2, BCL2, GABPA, HMOX1, KEAP1, MAPK8
cytosol 7 AIMP2, ANXA5, BCL2, FSCN1, HMOX1, KEAP1, MAPK8
nucleoplasm 4 GABPA, HMOX1, KEAP1, MAPK8
Cell membrane 1 TNF
Cytoplasmic side 1 HMOX1
lamellipodium 1 FSCN1
Multi-pass membrane protein 3 CYP19A1, KCNA3, SLC45A2
Synapse 1 MAPK8
cell cortex 1 FSCN1
cell junction 1 FSCN1
cell surface 1 TNF
glutamatergic synapse 1 KCNA3
Golgi membrane 1 INS
growth cone 1 FSCN1
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 1 TNF
presynaptic membrane 1 KCNA3
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 AIMP2, FSCN1
plasma membrane 3 KCNA3, TNF, UGT1A1
Membrane 9 AIMP2, ANXA5, BCL2, CYP19A1, CYP1B1, HMOX1, KCNA3, SLC45A2, UGT1A1
axon 2 KCNA3, MAPK8
caveola 1 PTGS2
extracellular exosome 3 ANXA5, FSCN1, SOD2
endoplasmic reticulum 6 BCL2, CYP19A1, HMOX1, KEAP1, PTGS2, UGT1A1
extracellular space 4 HMOX1, IL6, INS, TNF
perinuclear region of cytoplasm 3 HMOX1, KCNA3, UGT1A1
mitochondrion 4 BCL2, CYP1A1, CYP1B1, SOD2
protein-containing complex 2 BCL2, PTGS2
intracellular membrane-bounded organelle 3 CYP1A1, CYP1A2, CYP1B1
Microsome membrane 5 CYP19A1, CYP1A1, CYP1A2, CYP1B1, PTGS2
filopodium 1 FSCN1
Secreted 2 IL6, INS
extracellular region 4 ANXA5, IL6, INS, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 2 BCL2, UGT1A1
mitochondrial outer membrane 2 BCL2, HMOX1
Mitochondrion matrix 1 SOD2
mitochondrial matrix 1 SOD2
centriolar satellite 1 KEAP1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 ANXA5, TNF
actin cytoskeleton 1 FSCN1
Melanosome membrane 1 SLC45A2
midbody 1 KEAP1
cell-cell junction 1 FSCN1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 KCNA3
Cytoplasm, perinuclear region 1 UGT1A1
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 2 KCNA3, TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 FSCN1
focal adhesion 1 ANXA5
mitochondrial nucleoid 1 SOD2
collagen-containing extracellular matrix 1 ANXA5
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, filopodium 1 FSCN1
ruffle 1 FSCN1
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
chromatin 1 GABPA
phagocytic cup 1 TNF
cytoskeleton 1 FSCN1
podosome 1 FSCN1
Cytoplasm, cell cortex 1 FSCN1
actin filament 1 KEAP1
[Isoform 2]: Cell membrane 1 KCNA3
Cul3-RING ubiquitin ligase complex 1 KEAP1
endosome lumen 1 INS
microvillus 1 FSCN1
Cell projection, microvillus 1 FSCN1
myelin sheath 1 BCL2
stress fiber 1 FSCN1
voltage-gated potassium channel complex 1 KCNA3
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 IL6, INS, PTGS2
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
Single-pass type IV membrane protein 1 HMOX1
calyx of Held 1 KCNA3
vesicle membrane 1 ANXA5
Cytoplasm, cytoskeleton, stress fiber 1 FSCN1
basal dendrite 1 MAPK8
[Isoform 1]: Cell membrane 1 KCNA3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
microspike 1 FSCN1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
inclusion body 1 KEAP1
interleukin-6 receptor complex 1 IL6
endoplasmic reticulum chaperone complex 1 UGT1A1
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
cell projection membrane 1 FSCN1
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
cytochrome complex 1 UGT1A1
Cell projection, invadopodium 1 FSCN1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Nadja Kampschulte, Tim Berking, Ibrahim E Çelik, Stefan F Kirsch, Nils Helge Schebb. Inhibition of cytochrome P450 monooxygenase-catalyzed oxylipin formation by flavonoids: Evaluation of structure-activity relationship towards CYP4F2-selective inhibitors. European journal of medicinal chemistry. 2022 Aug; 238(?):114332. doi: 10.1016/j.ejmech.2022.114332. [PMID: 35576701]
  • Yannan Li, Jing Ning, Yan Wang, Chao Wang, Chengpeng Sun, Xiaokui Huo, Zhenlong Yu, Lei Feng, Baojing Zhang, Xiangge Tian, Xiaochi Ma. Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicology letters. 2018 Sep; 294(?):27-36. doi: 10.1016/j.toxlet.2018.05.008. [PMID: 29753067]
  • Elina Karhu, Janne Isojärvi, Pia Vuorela, Leena Hanski, Adyary Fallarero. Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy. Journal of natural products. 2017 10; 80(10):2602-2608. doi: 10.1021/acs.jnatprod.6b01052. [PMID: 29043803]
  • Bidisha Sengupta, Mehdi Sahihi, Monireh Dehkhodaei, Darrian Kelly, Istvan Arany. Differential roles of 3-Hydroxyflavone and 7-Hydroxyflavone against nicotine-induced oxidative stress in rat renal proximal tubule cells. PloS one. 2017; 12(6):e0179777. doi: 10.1371/journal.pone.0179777. [PMID: 28640852]
  • Lucie Zemanova, Jakub Hofman, Eva Novotna, Kamil Musilek, Tereza Lundova, Jana Havrankova, Anna Hostalkova, Jakub Chlebek, Lucie Cahlikova, Vladimír Wsol. Flavones Inhibit the Activity of AKR1B10, a Promising Therapeutic Target for Cancer Treatment. Journal of natural products. 2015 Nov; 78(11):2666-74. doi: 10.1021/acs.jnatprod.5b00616. [PMID: 26529431]
  • Bidisha Sengupta, Samantha M Reilly, Donald E Davis, Kisa Harris, Randy M Wadkins, Denise Ward, D'Asia Gholar, Cari Hampton. Excited state proton transfer of natural flavonoids and their chromophores in duplex and tetraplex DNAs. The journal of physical chemistry. B. 2015 Feb; 119(6):2546-56. doi: 10.1021/jp508599h. [PMID: 25393681]
  • Ragini Sinha, Akshada Joshi, Urmila J Joshi, Sudha Srivastava, Girjesh Govil. Localization and interaction of hydroxyflavones with lipid bilayer model membranes: a study using DSC and multinuclear NMR. European journal of medicinal chemistry. 2014 Jun; 80(?):285-94. doi: 10.1016/j.ejmech.2014.04.054. [PMID: 24793879]
  • Daniela Ribeiro, Marisa Freitas, Sara M Tomé, Artur M S Silva, Graça Porto, Eurico J Cabrita, M Manuel B Marques, Eduarda Fernandes. Inhibition of LOX by flavonoids: a structure-activity relationship study. European journal of medicinal chemistry. 2014 Jan; 72(?):137-45. doi: 10.1016/j.ejmech.2013.11.030. [PMID: 24368208]
  • Elizabeth A Mazzio, Fran Close, Karam F A Soliman. The biochemical and cellular basis for nutraceutical strategies to attenuate neurodegeneration in Parkinson's disease. International journal of molecular sciences. 2011 Jan; 12(1):506-69. doi: 10.3390/ijms12010506. [PMID: 21340000]
  • 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]
  • Pamela Maher, Richard Dargusch, Jennifer L Ehren, Shinichi Okada, Kumar Sharma, David Schubert. Fisetin lowers methylglyoxal dependent protein glycation and limits the complications of diabetes. PloS one. 2011; 6(6):e21226. doi: 10.1371/journal.pone.0021226. [PMID: 21738623]
  • Shigemi Seo, Ichiro Mitsuhara, Jiao Feng, Takayoshi Iwai, Morifumi Hasegawa, Yuko Ohashi. Cyanide, a coproduct of plant hormone ethylene biosynthesis, contributes to the resistance of rice to blast fungus. Plant physiology. 2011 Jan; 155(1):502-14. doi: 10.1104/pp.110.162412. [PMID: 21075959]
  • Jianbo Xiao, Hui Cao, Yuanfeng Wang, Koichiro Yamamoto, Xinlin Wei. Structure-affinity relationship of flavones on binding to serum albumins: effect of hydroxyl groups on ring A. Molecular nutrition & food research. 2010 Jul; 54 Suppl 2(?):S253-60. doi: 10.1002/mnfr.200900454. [PMID: 20306480]
  • Muthu Kumaradoss Mohan Maruga Raja, Shri Hari Mishra. Comprehensive review of Clerodendrum phlomidis: a traditionally used bitter. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2010 Jun; 8(6):510-24. doi: 10.3736/jcim20100602. [PMID: 20550872]
  • Chi-Sheng Shia, Shang-Yuan Tsai, Sheng-Chu Kuo, Yu-Chi Hou, Pei-Dawn Lee Chao. Metabolism and pharmacokinetics of 3,3',4',7-tetrahydroxyflavone (fisetin), 5-hydroxyflavone, and 7-hydroxyflavone and antihemolysis effects of fisetin and its serum metabolites. Journal of agricultural and food chemistry. 2009 Jan; 57(1):83-9. doi: 10.1021/jf802378q. [PMID: 19090755]
  • Sudip Chaudhuri, Biswapathik Pahari, Pradeep K Sengupta. Ground and excited state proton transfer and antioxidant activity of 7-hydroxyflavone in model membranes: absorption and fluorescence spectroscopic studies. Biophysical chemistry. 2009 Jan; 139(1):29-36. doi: 10.1016/j.bpc.2008.09.018. [PMID: 18977065]
  • Osamu Kagami, Kazutoshi Shindo, Akiko Kyojima, Kazuyo Takeda, Hiroshi Ikenaga, Kensuke Furukawa, Norihiko Misawa. Protein engineering on biphenyl dioxygenase for conferring activity to convert 7-hydroxyflavone and 5,7-dihydroxyflavone (chrysin). Journal of bioscience and bioengineering. 2008 Aug; 106(2):121-7. doi: 10.1263/jbb.106.121. [PMID: 18804053]
  • Sarah M Mense, Tom K Hei, Ramesh K Ganju, Hari K Bhat. Phytoestrogens and breast cancer prevention: possible mechanisms of action. Environmental health perspectives. 2008 Apr; 116(4):426-33. doi: 10.1289/ehp.10538. [PMID: 18414622]
  • Anwesha Banerjee, Kaushik Basu, Pradeep K Sengupta. Interaction of 7-hydroxyflavone with human serum albumin: a spectroscopic study. Journal of photochemistry and photobiology. B, Biology. 2008 Jan; 90(1):33-40. doi: 10.1016/j.jphotobiol.2007.10.005. [PMID: 18068375]
  • Petra Brozic, Tina Smuc, Stanislav Gobec, Tea Lanisnik Rizner. Phytoestrogens as inhibitors of the human progesterone metabolizing enzyme AKR1C1. Molecular and cellular endocrinology. 2006 Oct; 259(1-2):30-42. doi: 10.1016/j.mce.2006.08.001. [PMID: 16962702]
  • Tamara Stipcevic, Jasenka Piljac, Dirk Vanden Berghe. Effect of different flavonoids on collagen synthesis in human fibroblasts. Plant foods for human nutrition (Dordrecht, Netherlands). 2006 Mar; 61(1):29-34. doi: 10.1007/s11130-006-0006-8. [PMID: 16642409]
  • Jan Schraml, Vratislav Blechta, Jan Sýkora, Ludmila Soukupová, Petra Curínová, David Pronek, Jaromír Lachman. Characterization of polyphenols from plant materials through their silylation and 29Si NMR spectroscopy-line assignment through 29Si, 13C spin-spin couplings. Magnetic resonance in chemistry : MRC. 2005 Oct; 43(10):829-34. doi: 10.1002/mrc.1638. [PMID: 16041773]
  • Opa Vajragupta, Preecha Boonchoong, Yaowared Sumanont, Hiroshi Watanabe, Yuvadee Wongkrajang, Naparat Kammasud. Manganese-based complexes of radical scavengers as neuroprotective agents. Bioorganic & medicinal chemistry. 2003 May; 11(10):2329-37. doi: 10.1016/s0968-0896(03)00070-1. [PMID: 12713845]
  • N Saarinen, S C Joshi, M Ahotupa, X Li, J Ammälä, S Mäkelä, R Santti. No evidence for the in vivo activity of aromatase-inhibiting flavonoids. The Journal of steroid biochemistry and molecular biology. 2001 Sep; 78(3):231-9. doi: 10.1016/s0960-0760(01)00098-x. [PMID: 11595503]
  • A P Femia, G Caderni, C Buzzigoli, E Cocca, M Salvadori, P Dolara. Effect of simple phenolic compounds on azoxymethane-induced aberrant crypt foci in rat colon. Nutrition and cancer. 2001; 41(1-2):107-10. doi: 10.1080/01635581.2001.9680620. [PMID: 12094612]
  • L Costantino, G Rastelli, M C Gamberini, J A Vinson, P Bose, A Iannone, M Staffieri, L Antolini, A Del Corso, U Mura, A Albasini. 1-Benzopyran-4-one antioxidants as aldose reductase inhibitors. Journal of medicinal chemistry. 1999 Jun; 42(11):1881-93. doi: 10.1021/jm980441h. [PMID: 10354396]
  • S Moro, A M van Rhee, L H Sanders, K A Jacobson. Flavonoid derivatives as adenosine receptor antagonists: a comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model. Journal of medicinal chemistry. 1998 Jan; 41(1):46-52. doi: 10.1021/jm970446z. [PMID: 9438021]
  • X D Ji, N Melman, K A Jacobson. Interactions of flavonoids and other phytochemicals with adenosine receptors. Journal of medicinal chemistry. 1996 Feb; 39(3):781-8. doi: 10.1021/jm950661k. [PMID: 8576921]
  • M D Green, E M Oturu, T R Tephly. Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates. Drug metabolism and disposition: the biological fate of chemicals. 1994 Sep; 22(5):799-805. doi: NULL. [PMID: 7835232]
  • . . . . doi: . [PMID: 18487633]