Quercetin 3-O-glucuronide (BioDeep_00000018679)

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite

代谢物信息卡片

6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

化学式: C21H18O13 (478.0747378)
中文名称: 槲皮素-3-O-葡萄糖醛酸苷
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O
InChI: InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)

描述信息

Quercetin 3-O-glucuronide is a cocoa and tea metabolite in plasma and urine.
Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid.
Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid.

同义名列表

11 个代谢物同义名

6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid; 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate; Quercetin-3-glucuronidequercetin glucuronide; quercetin 3-O-beta-D-glucopyranoside; quercetin 3-O-beta-glucopyranoside; Quercetin 3-o-glucopyranoside; quercetin 3-O-glucuronide; QUERCETIN-3-O-GLUCURONIDE; Quercetin 3-glucuronide; Querciturone; Miquelianin

数据库引用编号

8 个数据库交叉引用编号

PubChem: 12004528
HMDB: HMDB0029212
ChEMBL: CHEMBL1506682
foodb: FDB031347
chemspider: 10176995
CAS: 22688-79-5
PMhub: MS000010080
medchemexpress: HY-13930

分类词条

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)

87 个相关的物种来源信息

174649 Rumex crispus: 10.1016/0305-1978(93)90049-W
1006352 Rumex dentatus: 10.1016/0305-1978(93)90049-W
291098 Rumex pulcher: 10.1016/0305-1978(93)90049-W
436212 Arnica sachalinensis: 10.1016/0305-1978(90)90026-C
39354 Salvia abrotanoides: 10.1016/S0031-9422(01)00415-0
1685717 Salvia syriaca: 10.1016/S0031-9422(01)00415-0
1933716 Salvia cyanescens: 10.1016/S0031-9422(01)00415-0
2039553 Salvia xalapensis: 10.1016/S0031-9422(01)00415-0
57936 Rubus chamaemorus: 10.1021/JF049450R
3746 Fragaria:
32247 Rubus idaeus:
29760 Vitis vinifera:
1053357 Hypericum undulatum: 10.1007/BF00630668
1647799 Mycoacia fuscoatra: 10.1055/S-2000-8633
43069 Centella erecta: 10.1055/S-0029-1240864
48106 Centella asiatica: 10.1055/S-0029-1240864
282542 Hypericum japonicum: 10.1016/J.PHYTOCHEM.2006.11.026
673928 Hypericum hirsutum: 10.1016/J.PHYTOCHEM.2006.11.026
1137007 Hypericum papuanum: 10.1016/J.PHYTOCHEM.2006.11.026
1136989 Hypericum laricifolium: 10.1016/J.PHYTOCHEM.2006.11.026
57926 Potentilla anserina: 10.1080/10286020.2010.489826
74647 Rosa multiflora: 10.1248/CPB.40.2080
41608 Mutisia acuminata:
3916 Vigna radiata var. radiata: 10.1007/BF00633405
668956 Persicaria thunbergii:
371026 Bistorta vivipara:
487741 Bistorta affinis:
46901 Persicaria hydropiper: 10.1021/NP9900674
137693 Polygonum aviculare:
371028 Persicaria perfoliata:
1331743 Ostericum citriodorum: 10.1016/0305-1978(86)90090-6
1129971 Euphorbia ampliphylla: 10.1016/S0031-9422(00)83562-1
4337 Anagallis arvensis: 10.1016/S0305-1978(98)00008-8
3505 Betula pendula:
38787 Betula pubescens: 10.1016/S0021-9673(97)00900-X
254780 Persicaria amphibia: 10.1016/S0031-9422(02)00504-6
580470 Persicaria decipiens: 10.1016/S0031-9422(02)00504-6
76025 Fallopia multiflora: 10.1007/BF02975130
3504 Betula: 10.1007/BF02260782
55963 Hypericum calycinum: 10.1073/PNAS.231471698
63791 Corsinia coriandrina: 10.1016/0305-1978(80)90019-8
482945 Populus grandidentata: 10.1021/JO01040A542
174649 Rumex crispus: 10.1016/0305-1978(93)90049-W
1006352 Rumex dentatus: 10.1016/0305-1978(93)90049-W
291098 Rumex pulcher: 10.1016/0305-1978(93)90049-W
436212 Arnica sachalinensis: 10.1016/0305-1978(90)90026-C
39354 Salvia abrotanoides: 10.1016/S0031-9422(01)00415-0
1685717 Salvia syriaca: 10.1016/S0031-9422(01)00415-0
1933716 Salvia cyanescens: 10.1016/S0031-9422(01)00415-0
2039553 Salvia xalapensis: 10.1016/S0031-9422(01)00415-0
57936 Rubus chamaemorus: 10.1021/JF049450R
3746 Fragaria:
32247 Rubus idaeus:
29760 Vitis vinifera:
1053357 Hypericum undulatum: 10.1007/BF00630668
1647799 Mycoacia fuscoatra: 10.1055/S-2000-8633
43069 Centella erecta: 10.1055/S-0029-1240864
48106 Centella asiatica: 10.1055/S-0029-1240864
282542 Hypericum japonicum: 10.1016/J.PHYTOCHEM.2006.11.026
673928 Hypericum hirsutum: 10.1016/J.PHYTOCHEM.2006.11.026
1137007 Hypericum papuanum: 10.1016/J.PHYTOCHEM.2006.11.026
1136989 Hypericum laricifolium: 10.1016/J.PHYTOCHEM.2006.11.026
57926 Potentilla anserina: 10.1080/10286020.2010.489826
74647 Rosa multiflora: 10.1248/CPB.40.2080
41608 Mutisia acuminata:
3916 Vigna radiata var. radiata: 10.1007/BF00633405
668956 Persicaria thunbergii:
371026 Bistorta vivipara:
487741 Bistorta affinis:
46901 Persicaria hydropiper: 10.1021/NP9900674
137693 Polygonum aviculare:
371028 Persicaria perfoliata:
1331743 Ostericum citriodorum: 10.1016/0305-1978(86)90090-6
1129971 Euphorbia ampliphylla: 10.1016/S0031-9422(00)83562-1
4337 Anagallis arvensis: 10.1016/S0305-1978(98)00008-8
3505 Betula pendula:
38787 Betula pubescens: 10.1016/S0021-9673(97)00900-X
254780 Persicaria amphibia: 10.1016/S0031-9422(02)00504-6
580470 Persicaria decipiens: 10.1016/S0031-9422(02)00504-6
76025 Fallopia multiflora: 10.1007/BF02975130
3504 Betula: 10.1007/BF02260782
55963 Hypericum calycinum: 10.1073/PNAS.231471698
63791 Corsinia coriandrina: 10.1016/0305-1978(80)90019-8
482945 Populus grandidentata: 10.1021/JO01040A542
9606 Homo sapiens: -
16906 Cornus Officinalis Sieb. Et Zucc.: -
33090 Plants: -

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。

文献列表

Zhenyu Wang, Tian Yang, Maomao Zeng, Zhaojun Wang, Qiuming Chen, Jie Chen, Mark Christian, Zhiyong He. Mitophagy suppression by miquelianin-rich lotus leaf extract induces 'beiging' of white fat via AMPK/DRP1-PINK1/PARKIN signaling axis. Journal of the science of food and agriculture. 2023 Nov; ?(?):. doi: 10.1002/jsfa.13143. [PMID: 37991930]
Zhenyu Wang, Tian Yang, Maomao Zeng, Zhaojun Wang, Qiuming Chen, Jie Chen, Mark Christian, Zhiyong He. Miquelianin in Folium Nelumbinis extract promotes white-to-beige fat conversion via blocking AMPK/DRP1/mitophagy and modulating gut microbiota in HFD-fed mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2023 Oct; 181(?):114089. doi: 10.1016/j.fct.2023.114089. [PMID: 37804915]
Marí C Santos, Mariana Koetz, Andreas S L Mendez, Amélia T Henriques. Ultrasound-assisted extraction optimization and validation of ultra-performance liquid chromatographic method for the quantification of miquelianin in Cuphea glutinosa leaves. Talanta. 2020 Aug; 216(?):120988. doi: 10.1016/j.talanta.2020.120988. [PMID: 32456919]
Sameh R Hussein, Mona M Marzouk, Mona E S Kassem, Rasha R Abdel Latif, Reda S Mohammed. Chemosystematic significance of flavonoids isolated from Diplotaxis acris (Brassicaceae) and related taxa. Natural product research. 2017 Feb; 31(3):347-350. doi: 10.1080/14786419.2016.1226831. [PMID: 27589908]
Yu Geon Lee, Jeong-Yong Cho, Young-Min Kim, Jae-Hak Moon. Change in Flavonoid Composition and Antioxidative Activity during Fermentation of Onion (Allium cepa L.) by Leuconostoc mesenteroides with Different Salt Concentrations. Journal of food science. 2016 Jun; 81(6):C1385-93. doi: 10.1111/1750-3841.13329. [PMID: 27175820]
Shujing Jiang, Qi Liu, Yixi Xie, Hualiang Zeng, Li Zhang, Xinyu Jiang, Xiaoqing Chen. Separation of five flavonoids from tartary buckwheat (Fagopyrum tataricum (L.) Gaertn) grains via off-line two dimensional high-speed counter-current chromatography. Food chemistry. 2015 Nov; 186(?):153-9. doi: 10.1016/j.foodchem.2014.08.120. [PMID: 25976805]
Flora Tolentino, Priscila Alves de Araújo, Eduardo de Souza Marques, Marcel Petreanu, Sérgio Faloni de Andrade, Rivaldo Niero, Fábio F Perazzo, Paulo César Pires Rosa, Edson Luis Maistro. In vivo evaluation of the genetic toxicity of Rubus niveus Thunb. (Rosaceae) extract and initial screening of its potential chemoprevention against doxorubicin-induced DNA damage. Journal of ethnopharmacology. 2015 Apr; 164(?):89-95. doi: 10.1016/j.jep.2015.02.013. [PMID: 25681544]
Chao-Zhan Lin, Zhong-Xiang Zhao, Si-Min Xie, Ju-Hua Mao, Chen-Chen Zhu, Xiao-Hui Li, Bairi Zeren-dawa, Kangsa Suolang-qimei, Dun Zhu, Tian-Qin Xiong, Ai-Zhi Wu. Diterpenoid alkaloids and flavonoids from Delphinium trichophorum. Phytochemistry. 2014 Jan; 97(?):88-95. doi: 10.1016/j.phytochem.2013.10.011. [PMID: 24256579]
Khem Raj Joshi, Hari Prasad Devkota, Takashi Watanabe, Shoji Yahara. Phenolic compounds from the flowers of Nepalese medicinal plant Aconogonon molle and their DPPH free radical-scavenging activities. Natural product research. 2014; 28(23):2208-10. doi: 10.1080/14786419.2014.915829. [PMID: 24825068]
R S Mohammed, A H Abou Zeid, E A El-Kashoury, A A Sleem, D A Waly. A new flavonol glycoside and biological activities of Adenanthera pavonina L. leaves. Natural product research. 2014; 28(5):282-9. doi: 10.1080/14786419.2013.856903. [PMID: 24289202]
Mariela Beatriz Vera Saltos, Blanca Fabiola Naranjo Puente, Nicola Malafronte, Alessandra Braca. A new monoterpene glycoside from Siparuna thecaphora. Natural product research. 2014; 28(1):57-60. doi: 10.1080/14786419.2013.843179. [PMID: 24087860]
Xin Yao, Guisheng Zhou, Yuping Tang, Zhenhao Li, Shulan Su, Dawei Qian, Jin-Ao Duan. A UPLC-MS/MS method for qualification of quercetin-3-O-β-D-glucopyranoside-(4→1)-α-L-rhamnoside in rat plasma and application to pharmacokinetic studies. Molecules (Basel, Switzerland). 2013 Mar; 18(3):3050-9. doi: 10.3390/molecules18033050. [PMID: 23470334]
Anh Pham, Anthony Bortolazzo, J Brandon White. Rapid dimerization of quercetin through an oxidative mechanism in the presence of serum albumin decreases its ability to induce cytotoxicity in MDA-MB-231 cells. Biochemical and biophysical research communications. 2012 Oct; 427(2):415-20. doi: 10.1016/j.bbrc.2012.09.080. [PMID: 23000408]
W Nantitanon, S Okonogi. Comparison of antioxidant activity of compounds isolated from guava leaves and a stability study of the most active compound. Drug discoveries & therapeutics. 2012 Feb; 6(1):38-43. doi: 10.5582/ddt.2012.v6.1.38. [PMID: 22460427]
Hiroshi Shimoda, Seiko Nakamura, Makoto Morioka, Junji Tanaka, Hisashi Matsuda, Masayuki Yoshikawa. Effect of cinnamoyl and flavonol glucosides derived from cherry blossom flowers on the production of advanced glycation end products (AGEs) and AGE-induced fibroblast apoptosis. Phytotherapy research : PTR. 2011 Sep; 25(9):1328-35. doi: 10.1002/ptr.3423. [PMID: 21308824]
Hong-Li Liu, Bai-Lian Liu, Guo-Cai Wang, Yi Dai, Wen-Cai Ye, Yao-Lan Li. [Studies on the chemical constituents from Conyza canadensis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 May; 34(5):718-20. doi: . [PMID: 21954558]
Yan Yi, Xin Wu, Ying Wang, Wen-Cai Ye, Qing-Wen Zhang. [Studies on the flavonoids from the flowers of Hylocereus undatus]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 May; 34(5):712-6. doi: ". [PMID: 21954556]
Joo Hee Kwon, Jee Hun Kim, Sun Eun Choi, Kwan Hee Park, Min Won Lee. Inhibitory effects of phenolic compounds from needles of Pinus densiflora on nitric oxide and PGE2 production. Archives of pharmacal research. 2010 Dec; 33(12):2011-6. doi: 10.1007/s12272-010-1217-y. [PMID: 21191767]
Yong-hai Meng, Qiu-hong Wang, Hai Jiang, Bing-you Yang, Hai-xue Kuang. [Study on chemical constituents of Herba Cirsii]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Jan; 32(1):58-61. doi: . [PMID: 19445122]
Li-Guang Zhou, Xue-Song Feng, Kai-Yi Huang, Le He, Xu-Ming Deng, Da-Cheng Wang. [Studies on chemical constituents of Syringa veutina]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 May; 31(5):679-81. doi: . [PMID: 18826143]
Silvia Martini, Claudia Bonechi, Claudio Rossi. Interaction of quercetin and its conjugate quercetin 3-O-beta-D-glucopyranoside with albumin as determined by NMR relaxation data. Journal of natural products. 2008 Feb; 71(2):175-8. doi: 10.1021/np070285u. [PMID: 18197600]
Guido Juergenliemk, Kerstin Boje, Sabine Huewel, Christina Lohmann, Hans-Joachim Galla, Adolf Nahrstedt. In vitro studies indicate that miquelianin (quercetin 3-O-beta-D-glucuronopyranoside) is able to reach the CNS from the small intestine. Planta medica. 2003 Nov; 69(11):1013-7. doi: 10.1055/s-2003-45148. [PMID: 14735439]
H Lou, H Yuan, Y Yamazaki, T Sasaki, S Oka. Alkaloids and flavonoids from peanut skins. Planta medica. 2001 Jun; 67(4):345-9. doi: 10.1055/s-2001-14319. [PMID: 11458452]
E Luiz da Silva, T Tsushida, J Terao. Inhibition of mammalian 15-lipoxygenase-dependent lipid peroxidation in low-density lipoprotein by quercetin and quercetin monoglucosides. Archives of biochemistry and biophysics. 1998 Jan; 349(2):313-20. doi: 10.1006/abbi.1997.0455. [PMID: 9448720]