Isosakuranetin (BioDeep_00000267043)

Main id: BioDeep_00000000409

Secondary id: BioDeep_00000180187

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-, (2S)-

化学式: C16H14O5 (286.0841)
中文名称: 异野樱素, 异樱花亭, 异樱花素
谱图信息: 最多检出来源 Viridiplantae(otcml) 25.6%

分子结构信息

SMILES: c1(cc(c2c(c1)O[C@@H](CC2=O)c1ccc(cc1)OC)O)O
InChI: InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1

描述信息

4-methoxy-5,7-dihydroxyflavanone is a dihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5 and 7 and a methoxy group at position 4 (the 2S stereoisomer). It has a role as a plant metabolite. It is a dihydroxyflavanone, a monomethoxyflavanone, a member of 4-methoxyflavanones and a (2S)-flavan-4-one. It is functionally related to a (S)-naringenin.
Isosakuranetin is a natural product found in Ageratina altissima, Chromolaena odorata, and other organisms with data available.
A dihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5 and 7 and a methoxy group at position 4 (the 2S stereoisomer).
Isosakuranetin is a flavanone flavonoid which can be found in the fruit of Citrus bergamia.
Isosakuranetin is a flavanone flavonoid which can be found in the fruit of Citrus bergamia.

同义名列表

27 个代谢物同义名

4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-, (2S)-; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-, (S)-; (2S)-2,3-Dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one; (2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one; (S)-2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one; (2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one; (2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one; (S)-2,3-Dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone; (S)-5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one; (2S)-5,7-Dihydroxy-4-methoxyflavanone; 5,7-Dihydroxy-4-methoxyflavanone; 4-Methoxy-5,7-dihydroxyflavonone; 5,7-dihydroxy-4-methoxyflavanone; 4-methoxy-5,7-dihydroxyflavanone; (2S)-naringenin 4-methyl ether; HMUJXQRRKBLVOO-AWEZNQCLSA-N; naringenin 4-methyl ether; 4-Methylnaringenin; UNII-U02X7TF8UA; Isosakutanetin; Isosakuranetin; MEGxp0_001686; ACon1_000171; Citrifoliol; U02X7TF8UA; (S) -2,3-Dihydro-5,7-dihydroxy-2- (4-methoxyphenyl) -4H-1-benzopyran-4-one; Isosakuranetin



数据库引用编号

69 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)

195 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 12 AIMP2, CASP3, CAT, EIF2AK3, JAK1, JAK3, MAPK8, MAPK9, NR1I3, PIK3CA, TYRP1, XDH
Peripheral membrane protein 1 JAK3
Endosome membrane 1 TYRP1
Endoplasmic reticulum membrane 1 EIF2AK3
Nucleus 10 AIMP2, CASP3, EIF2AK3, FOS, HCK, JAK1, MAPK8, MAPK9, NR1I2, NR1I3
cytosol 13 AIMP2, CASP3, CAT, EIF2AK3, FOS, HCK, JAK1, JAK3, MAPK8, MAPK9, NR1I3, PIK3CA, XDH
nuclear body 1 NR1I2
nucleoplasm 6 CASP3, FOS, MAPK8, MAPK9, NR1I2, NR1I3
RNA polymerase II transcription regulator complex 1 FOS
Cell membrane 2 TNF, TRPM3
Lipid-anchor 1 HCK
lamellipodium 1 PIK3CA
Multi-pass membrane protein 2 CATSPER3, TRPM3
Synapse 1 MAPK8
cell surface 2 TNF, TNR
glutamatergic synapse 2 CASP3, TNR
Golgi apparatus 1 HCK
Golgi membrane 1 INS
neuronal cell body 2 CASP3, TNF
Cytoplasm, cytosol 1 AIMP2
Lysosome 1 HCK
acrosomal vesicle 1 CATSPER3
endosome 2 JAK1, JAK3
plasma membrane 8 CATSPER3, HCK, JAK1, JAK3, MAPK9, PIK3CA, TNF, TRPM3
Membrane 6 AIMP2, CAT, EIF2AK3, JAK1, JAK3, TRPM3
axon 1 MAPK8
caveola 1 HCK
extracellular exosome 1 CAT
endoplasmic reticulum 3 CATSPER3, EIF2AK3, FOS
extracellular space 4 INS, TNF, TNR, XDH
perinuclear region of cytoplasm 2 EIF2AK3, PIK3CA
Schaffer collateral - CA1 synapse 2 MAPK9, TNR
intercalated disc 1 PIK3CA
mitochondrion 2 CAT, MAPK9
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 2 CAT, HCK
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 EIF2AK3, TYRP1
Secreted 1 INS
extracellular region 4 CAT, INS, TNF, TNR
cytoplasmic side of plasma membrane 3 HCK, JAK1, JAK3
mitochondrial matrix 1 CAT
transcription regulator complex 1 NR1I2
motile cilium 1 CATSPER3
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 1 TNR
cytoplasmic vesicle 1 HCK
Melanosome membrane 1 TYRP1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 2 TNF, TNR
Cell junction, focal adhesion 1 HCK
Cytoplasm, cytoskeleton 2 HCK, NR1I3
focal adhesion 3 CAT, HCK, JAK1
Peroxisome 2 CAT, XDH
intracellular vesicle 1 TYRP1
sarcoplasmic reticulum 1 XDH
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 TNR
nuclear speck 1 MAPK9
chromatin 3 FOS, NR1I2, NR1I3
cell projection 1 HCK
phagocytic cup 1 TNF
cytoskeleton 4 HCK, JAK1, JAK3, NR1I3
[Isoform 2]: Cell membrane 1 HCK
Endomembrane system 2 JAK1, JAK3
endosome lumen 1 INS
Membrane, caveola 1 HCK
Cell projection, cilium, flagellum membrane 1 CATSPER3
Melanosome 1 TYRP1
intermediate filament cytoskeleton 1 NR1I2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
nuclear matrix 1 FOS
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
transport vesicle 2 HCK, INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
perineuronal net 1 TNR
clathrin-coated endocytic vesicle membrane 1 TYRP1
extrinsic component of cytoplasmic side of plasma membrane 2 JAK1, JAK3
protein-DNA complex 1 FOS
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
extrinsic component of plasma membrane 1 JAK3
transcription factor AP-1 complex 1 FOS
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
tenascin complex 1 TNR
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
CatSper complex 1 CATSPER3
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Xuedan Cao, Xiao Guo, Xiugui Fang, Shuijiang Ru, Erhu Li. Effects of Poncirin, a Citrus Flavonoid and Its Aglycone, Isosakuranetin, on the Gut Microbial Diversity and Metabolomics in Mice. Molecules (Basel, Switzerland). 2022 Jun; 27(11):. doi: 10.3390/molecules27113641. [PMID: 35684581]
  • Steven J Kleene, Brian J Siroky, Julio A Landero-Figueroa, Bradley P Dixon, Nolan W Pachciarz, Lu Lu, Nancy K Kleene. The TRPP2-dependent channel of renal primary cilia also requires TRPM3. PloS one. 2019; 14(3):e0214053. doi: 10.1371/journal.pone.0214053. [PMID: 30883612]
  • Geum-Dan Kang, Dong-Hyun Kim. Ponciretin attenuates ethanol-induced gastric damage in mice by inhibiting inflammatory responses. International immunopharmacology. 2017 Feb; 43(?):179-186. doi: 10.1016/j.intimp.2016.12.021. [PMID: 28013186]
  • Shushan Jia, Yong Zhang, Jingui Yu. Antinociceptive Effects of Isosakuranetin in a Rat Model of Peripheral Neuropathy. Pharmacology. 2017; 100(3-4):201-207. doi: 10.1159/000478986. [PMID: 28715803]
  • Shyi-Neng Lou, Yi-Chun Lai, Ya-Siou Hsu, Chi-Tang Ho. Phenolic content, antioxidant activity and effective compounds of kumquat extracted by different solvents. Food chemistry. 2016 Apr; 197(Pt A):1-6. doi: 10.1016/j.foodchem.2015.10.096. [PMID: 26616917]
  • Jin-Song Liu, Ai-Min Chen, Ying-Sheng Xu, Gang Wang, Guo-Kai Wang. [Phenolic derivatives from Wisteria sinensis sweet caulis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2013 Sep; 36(9):1437-40. doi: . [PMID: 24620688]
  • Gaurav Swarnkar, Kunal Sharan, Jawed A Siddiqui, Jay Sharan Mishra, Kainat Khan, Mohd Parvez Khan, Varsha Gupta, Preeti Rawat, Rakesh Maurya, Anil K Dwivedi, Sabyasachi Sanyal, Naibedya Chattopadhyay. A naturally occurring naringenin derivative exerts potent bone anabolic effects by mimicking oestrogen action on osteoblasts. British journal of pharmacology. 2012 Mar; 165(5):1526-42. doi: 10.1111/j.1476-5381.2011.01637.x. [PMID: 21864313]
  • Jie Zhang, Linxi Li, Xiuhua Liu, Yong Wang, Dongbao Zhao. [Study on chemical constituents of Artemisia sphaerocephala]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Jan; 37(2):238-42. doi: . [PMID: 22737859]
  • Andresa Aparecida Berretta, Andresa Piacezzi Nascimento, Paula Carolina Pires Bueno, Mirela Mara de Oliveira Lima Leite Vaz, Juliana Maldonado Marchetti. Propolis standardized extract (EPP-AF®), an innovative chemically and biologically reproducible pharmaceutical compound for treating wounds. International journal of biological sciences. 2012; 8(4):512-21. doi: 10.7150/ijbs.3641. [PMID: 22457606]
  • Pascal Wafo, Ramsay S T Kamdem, Zulfiqar Ali, Shazia Anjum, Afshan Begum, Ogbole O Oluyemisi, Shamsun N Khan, Bonaventure T Ngadjui, Xavier F Etoa, Muhammed Iqbal Choudhary. Kaurane-type diterpenoids from Chromoleana odorata, their X-ray diffraction studies and potent α-glucosidase inhibition of 16-kauren-19-oic acid. Fitoterapia. 2011 Jun; 82(4):642-6. doi: 10.1016/j.fitote.2011.02.003. [PMID: 21316426]
  • Karina R Vega-Villa, Connie M Remsberg, Jody K Takemoto, Yusuke Ohgami, Jaime A Yáñez, Preston K Andrews, Neal M Davies. Stereospecific pharmacokinetics of racemic homoeriodictyol, isosakuranetin, and taxifolin in rats and their disposition in fruit. Chirality. 2011 Apr; 23(4):339-48. doi: 10.1002/chir.20926. [PMID: 21384439]
  • Xiaona Fan, Sheng Lin, Chenggen Zhu, Yang Liu, Jinfeng Hu, Xiaoguang Chen, Wenjie Wang, Naihong Chen, Jiangong Shi. [Aromatic constituents of Heteroplexis micocephal and their bioactivities]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Jan; 36(1):48-56. doi: . [PMID: 21473152]
  • João Paulo B de Sousa, Mateus F Leite, Renata F Jorge, Dimas O Resende, Ademar A da Silva Filho, Niege A J C Furtado, Ademilson E E Soares, Augusto C C Spadaro, Pedro Melillo de Magalhães, Jairo K Bastos. Seasonality Role on the Phenolics from Cultivated Baccharis dracunculifolia. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):464289. doi: 10.1093/ecam/nep077. [PMID: 19605554]
  • Marica Medić-Sarić, Vesna Rastija, Mirza Bojić, Zeljan Males. From functional food to medicinal product: systematic approach in analysis of polyphenolics from propolis and wine. Nutrition journal. 2009 Jul; 8(?):33. doi: 10.1186/1475-2891-8-33. [PMID: 19624827]
  • Karina R Vega-Villa, Connie M Remsberg, Kristy L Podelnyk, Neal M Davies. Stereospecific high-performance liquid chromatographic assay of isosakuranetin in rat urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Nov; 875(1):142-7. doi: 10.1016/j.jchromb.2008.05.018. [PMID: 18514595]
  • Bruno B Silva, Pedro L Rosalen, Jaime A Cury, Masaharu Ikegaki, Vinícius C Souza, Alessandro Esteves, Severino M Alencar. Chemical composition and botanical origin of red propolis, a new type of brazilian propolis. Evidence-based complementary and alternative medicine : eCAM. 2008 Sep; 5(3):313-6. doi: 10.1093/ecam/nem059. [PMID: 18830449]
  • W Wätjen, A K Suckow-Schnitker, R Rohrig, A Kulawik, J Addae-Kyereme, C W Wright, C M Passreiter. Prenylated flavonoid derivatives from the bark of Erythrina addisoniae. Journal of natural products. 2008 Apr; 71(4):735-8. doi: 10.1021/np070417j. [PMID: 18302333]
  • Ademar A da Silva Filho, Joo P B de Sousa, Sandra Soares, Niege A J C Furtado, Mircio L Andrade e Silva, Wilson R Cunha, Luís E Gregório, N P Dhammika Nanayakkara, Jairo K Bastos. Antimicrobial activity of the extract and isolated compounds from Baccharis dracunculifolia D. C. (Asteraceae). Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Jan; 63(1-2):40-6. doi: 10.1515/znc-2008-1-208. [PMID: 18386486]
  • Denise Crispim Tavares, Walclécio Morais Lira, Camila Bastianini Santini, Catarina Satie Takahashi, Jairo Kenupp Bastos. Effects of propolis crude hydroalcoholic extract on chromosomal aberrations induced by doxorubicin in rats. Planta medica. 2007 Dec; 73(15):1531-6. doi: 10.1055/s-2007-993737. [PMID: 17999350]
  • Fabiane Missima, Ademar A da Silva Filho, Gladston A Nunes, Paula C Pires Bueno, João Paulo B de Sousa, Jairo K Bastos, Jose M Sforcin. Effect of Baccharis dracunculifolia D.C. (Asteraceae) extracts and its isolated compounds on macrophage activation. The Journal of pharmacy and pharmacology. 2007 Mar; 59(3):463-8. doi: 10.1211/jpp.59.3.0017. [PMID: 17331351]
  • João Henrique G Lago, Clécio Sousa Ramos, Diego Campos C Casanova, Andreia de A Morandim, Debora Cristina B Bergamo, Alberto J Cavalheiro, Vanderlan da S Bolzani, Maysa Furlan, Elsie F Guimarães, Maria Claudia M Young, Massuo J Kato. Benzoic acid derivatives from Piper species and their fungitoxic activity against Cladosporium cladosporioides and C. sphaerospermum. Journal of natural products. 2004 Nov; 67(11):1783-8. doi: 10.1021/np030530j. [PMID: 15568762]
  • L M C Simões, L E Gregório, A A Da Silva Filho, M L de Souza, A E C S Azzolini, J K Bastos, Y M Lucisano-Valim. Effect of Brazilian green propolis on the production of reactive oxygen species by stimulated neutrophils. Journal of ethnopharmacology. 2004 Sep; 94(1):59-65. doi: 10.1016/j.jep.2004.04.026. [PMID: 15261964]
  • Ademar A da Silva Filho, Paula C Pires Bueno, Luís E Gregório, Márcio L Andrade e Silva, Sérgio Albuquerque, Jairo K Bastos. In-vitro trypanocidal activity evaluation of crude extract and isolated compounds from Baccharis dracunculifolia D.C. (Asteraceae). The Journal of pharmacy and pharmacology. 2004 Sep; 56(9):1195-9. doi: 10.1211/0022357044067. [PMID: 15324490]
  • Kazuo Shimizu, Hitoshi Ashida, Yukinaga Matsuura, Kazuki Kanazawa. Antioxidative bioavailability of artepillin C in Brazilian propolis. Archives of biochemistry and biophysics. 2004 Apr; 424(2):181-8. doi: 10.1016/j.abb.2004.02.021. [PMID: 15047190]