3'-Hydroxygenistein (BioDeep_00000004323)

 

Secondary id: BioDeep_00000270595

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-Benzopyran-4-one, 3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-

化学式: C15H10O6 (286.0477)
中文名称: 奥洛波尔, 3',4',5,7-四羟基异黄酮
谱图信息: 最多检出来源 Chinese Herbal Medicine(urine) 37.82%

分子结构信息

SMILES: c1(cc(c2c(c1)occ(c2=O)c1ccc(c(c1)O)O)O)O
InChI: InChI=1S/C15H10O6/c16-8-4-12(19)14-13(5-8)21-6-9(15(14)20)7-1-2-10(17)11(18)3-7/h1-6,16-19H

描述信息

Orobol is a member of the class of 7-hydroxyisoflavones which consists of isoflavone substituted by hydroxy groups at positions 5, 7, 3 and 4. It has been isolated from the mycelia of Cordyceps sinensis. It has a role as an anti-inflammatory agent, a radical scavenger, a plant metabolite and a fungal metabolite. It is functionally related to an isoflavone.
Orobol is a natural product found in Tritirachium, Ammopiptanthus mongolicus, and other organisms with data available.
A member of the class of 7-hydroxyisoflavones which consists of isoflavone substituted by hydroxy groups at positions 5, 7, 3 and 4. It has been isolated from the mycelia of Cordyceps sinensis.
3-Hydroxygenistein is a polyphenol metabolite detected in biological fluids (PMID: 20428313).
A polyphenol metabolite detected in biological fluids [PhenolExplorer]

同义名列表

24 个代谢物同义名

4H-1-Benzopyran-4-one, 3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(3,4-dihydroxyphenyl)-; 5,7-Dihydroxy-3-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one; 3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one; 5,7-dihydroxy-3-(3,4-dihydroxyphenyl)-4-1H-benzopyran-4-one; 3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one; 3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one; 3-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one; 5-18-05-00318 (Beilstein Handbook Reference); 5-HYDROXY-1H-INDAZOLE-3-CARBOXYLICACID; Isoflavone, 3,4,5,7-tetrahydroxy-; 5,7,3,4-Tetrahydroxyisoflavone; 3,4,5,7-Tetrahydroxyisoflavone; 5,3,4-Tetrahydroxyisoflavone; 3-hydroxy-genistein; 3-hydroxygenistein; UNII-LU8UZM1T51; isoluteolin; LU8UZM1T51; Norsantal; Quercitin; Orobol; Santol; Orobol



数据库引用编号

23 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)

27 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 7 AIMP2, CSNK1E, EIF4EBP1, IL13, NFKBIA, TH, TYR
Peripheral membrane protein 2 ACHE, CYP1B1
Endosome membrane 1 ATR
Endoplasmic reticulum membrane 2 CYP1B1, POR
Nucleus 9 ACHE, AIMP2, ATR, CSNK1E, EIF4EBP1, KRT16, NFKBIA, PBK, TH
cytosol 7 AIMP2, CSNK1E, EIF4EBP1, KRT16, NFKBIA, POR, TH
dendrite 1 TH
nucleoplasm 3 ATR, CSNK1E, NFKBIA
Cell membrane 2 ACHE, ATR
Cytoplasmic side 1 POR
Cell projection, axon 1 TH
Synapse 1 ACHE
cell surface 2 ACHE, ATR
Golgi apparatus 2 ACHE, ATR
Golgi membrane 1 INS
growth cone 1 CSNK1E
neuromuscular junction 1 ACHE
neuronal cell body 1 CSNK1E
smooth endoplasmic reticulum 1 TH
synaptic vesicle 1 TH
Cytoplasm, cytosol 1 AIMP2
Lysosome 1 TYR
plasma membrane 5 ACHE, ATR, IFNLR1, IGHE, NFKBIA
terminal bouton 1 TH
Membrane 6 ACHE, AIMP2, CSNK1E, CYP1B1, IFNLR1, POR
axon 1 TH
extracellular exosome 1 KRT16
endoplasmic reticulum 2 ATR, POR
extracellular space 9 ACHE, ATR, CCL17, IGHE, IL13, IL4, IL5, IL6, INS
perinuclear region of cytoplasm 3 ACHE, TH, TYR
mitochondrion 2 CYP1B1, TH
intracellular membrane-bounded organelle 3 CYP1B1, POR, TYR
Microsome membrane 1 CYP1B1
Single-pass type I membrane protein 4 ATR, IFNLR1, IGHE, TYR
Secreted 7 ACHE, CCL17, IL13, IL4, IL5, IL6, INS
extracellular region 8 ACHE, CCL17, IGHE, IL13, IL4, IL5, IL6, INS
cytoplasmic side of plasma membrane 1 TH
Single-pass membrane protein 1 POR
Extracellular side 1 ACHE
external side of plasma membrane 2 ATR, IL13
perikaryon 1 TH
cytoplasmic vesicle 1 TH
Melanosome membrane 2 TH, TYR
Golgi-associated vesicle 1 TYR
Cytoplasm, perinuclear region 1 TH
basement membrane 1 ACHE
PML body 1 ATR
intermediate filament 1 KRT16
neuron projection 1 TH
IgE immunoglobulin complex 1 IGHE
Chromosome 1 ATR
cytoskeleton 1 KRT16
Lipid-anchor, GPI-anchor 1 ACHE
[Isoform 2]: Cell membrane 1 IGHE
nuclear envelope 1 ATR
Nucleus envelope 1 ATR
endosome lumen 1 INS
Cornified envelope 1 KRT16
Melanosome 1 TYR
side of membrane 1 ACHE
filopodium membrane 1 ATR
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 IL6, INS
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
ribonucleoprotein complex 1 CSNK1E
synaptic cleft 1 ACHE
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
keratin filament 1 KRT16
site of DNA damage 1 ATR
Cell projection, filopodium membrane 1 ATR
[Isoform 3]: Cell membrane 1 IGHE
lamellipodium membrane 1 ATR
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
Cell projection, lamellipodium membrane 1 ATR
interleukin-6 receptor complex 1 IL6
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
I-kappaB/NF-kappaB complex 1 NFKBIA
[Isoform H]: Cell membrane 1 ACHE
interleukin-28 receptor complex 1 IFNLR1
ATR-ATRIP complex 1 ATR


文献列表

  • Hee Yang, Sang-Hyuk Lee, Hae Ji, Jong-Eun Kim, Ra Yoo, Jong Hun Kim, Sujin Suk, Chul Sung Huh, Jung Han Yoon Park, Yong-Seok Heo, Han-Seoung Shin, Byung-Gee Kim, Ki Won Lee. Orobol, an Enzyme-Convertible Product of Genistein, exerts Anti-Obesity Effects by Targeting Casein Kinase 1 Epsilon. Scientific reports. 2019 06; 9(1):8942. doi: 10.1038/s41598-019-43950-9. [PMID: 31222064]
  • Pyung-Gang Lee, Sang-Hyuk Lee, Eun Young Hong, Stefan Lutz, Byung-Gee Kim. Circular permutation of a bacterial tyrosinase enables efficient polyphenol-specific oxidation and quantitative preparation of orobol. Biotechnology and bioengineering. 2019 01; 116(1):19-27. doi: 10.1002/bit.26795. [PMID: 30011063]
  • Wei-Ping Lee, Keng-Li Lan, Shi-Xian Liao, Yi-Hsiang Huang, Ming-Chih Hou, Keng-Hsin Lan. Inhibitory Effects of Amentoflavone and Orobol on Daclatasvir-Induced Resistance-Associated Variants of Hepatitis C Virus. The American journal of Chinese medicine. 2018; 46(4):835-852. doi: 10.1142/s0192415x18500441. [PMID: 29737209]
  • Wenzhong Shi, Lili Liu, Jian Li, Lu Qu, Xu Pang, Haiyang Yu, Yi Zhang, Tao Wang. Bioactive flavonoids from Flos Sophorae. Journal of natural medicines. 2017 Jul; 71(3):513-522. doi: 10.1007/s11418-017-1084-7. [PMID: 28357634]
  • Chul Lee, Jin Woo Lee, Qinghao Jin, Dae Sik Jang, Sung-Joon Lee, Dongho Lee, Jin Tae Hong, Youngsoo Kim, Mi Kyeong Lee, Bang Yeon Hwang. Inhibitory constituents of the heartwood of Dalbergia odorifera on nitric oxide production in RAW 264.7 macrophages. Bioorganic & medicinal chemistry letters. 2013 Jul; 23(14):4263-6. doi: 10.1016/j.bmcl.2013.04.032. [PMID: 23743282]
  • Supinya Tewtrakul, Sanan Subhadhirasakul, Pimpimon Tansakul, Sarot Cheenpracha, Chatchanok Karalai. Antiinflammatory constituents from Eclipta prostrata using RAW264.7 macrophage cells. Phytotherapy research : PTR. 2011 Sep; 25(9):1313-6. doi: 10.1002/ptr.3383. [PMID: 21312307]
  • Monika Mueller, Stefanie Hobiger, Alois Jungbauer. Red clover extract: a source for substances that activate peroxisome proliferator-activated receptor alpha and ameliorate the cytokine secretion profile of lipopolysaccharide-stimulated macrophages. Menopause (New York, N.Y.). 2010 Mar; 17(2):379-87. doi: 10.1097/gme.0b013e3181c94617. [PMID: 20142789]
  • Quan Cheng Chen, Wei Yun Zhang, Wenyi Jin, Ik Soo Lee, Byung-Sun Min, Hyun-Ju Jung, Minkyun Na, Sangmyung Lee, Kihwan Bae. Flavonoids and isoflavonoids from Sophorae Flos improve glucose uptake in vitro. Planta medica. 2010 Jan; 76(1):79-81. doi: 10.1055/s-0029-1185944. [PMID: 19637114]
  • Yuzhen Guan, Zhiqi Yin, Lian Guo, Xiaojun Huang, Wencai Ye, Wenbin Shen. [Studies on chemical constituents from stems of Cudrania tricuspidata]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 May; 34(9):1108-10. doi: . [PMID: 19685745]
  • Monika Mueller, Alois Jungbauer. Red clover extract: a putative source for simultaneous treatment of menopausal disorders and the metabolic syndrome. Menopause (New York, N.Y.). 2008 Nov; 15(6):1120-31. doi: 10.1097/gme.0b013e31817062ce. [PMID: 18724264]
  • Angelika Pfitscher, Evelyne Reiter, Alois Jungbauer. Receptor binding and transactivation activities of red clover isoflavones and their metabolites. The Journal of steroid biochemistry and molecular biology. 2008 Nov; 112(1-3):87-94. doi: 10.1016/j.jsbmb.2008.08.007. [PMID: 18809497]
  • Supinya Tewtrakul, Sanan Subhadhirasakul, Sarot Cheenpracha, Chatchanok Karalai. HIV-1 protease and HIV-1 integrase inhibitory substances from Eclipta prostrata. Phytotherapy research : PTR. 2007 Nov; 21(11):1092-5. doi: 10.1002/ptr.2252. [PMID: 17696192]
  • Hisashi Matsuda, Kazutoshi Yoshida, Katsutoshi Miyagawa, Yasunobu Asao, Saya Takayama, Souichi Nakashima, Fengming Xu, Masayuki Yoshikawa. Rotenoids and flavonoids with anti-invasion of HT1080, anti-proliferation of U937, and differentiation-inducing activity in HL-60 from Erycibe expansa. Bioorganic & medicinal chemistry. 2007 Feb; 15(3):1539-46. doi: 10.1016/j.bmc.2006.09.024. [PMID: 17158054]
  • Rong Tsao, Yousef Papadopoulos, Raymond Yang, J Chris Young, Ken McRae. Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages. Journal of agricultural and food chemistry. 2006 Aug; 54(16):5797-805. doi: 10.1021/jf0614589. [PMID: 16881680]
  • Hyun Ah Jung, Hae Young Chung, Sam Sik Kang, Sook Kyung Hyun, Hye Sook Kang, Jae Sue Choi. A phenolic glucoside isolated from Prunus serrulata var. spontanea and its peroxynitrite scavenging activity. Archives of pharmacal research. 2005 Oct; 28(10):1127-30. doi: 10.1007/bf02972973. [PMID: 16276966]
  • A S Saratikov, V S Chuchalin, A V Rat'kin, E V Rat'kin, S A Fedoreev, V P Bulgakov. [Hepatoprotector properties of polyphenolic complexes from wood and cell culture of Maackia amurensis]. Eksperimental'naia i klinicheskaia farmakologiia. 2005 Mar; 68(2):51-4. doi: . [PMID: 15934369]
  • Hisashi Matsuda, Toshio Morikawa, Fengming Xu, Kiyofumi Ninomiya, Masayuki Yoshikawa. New isoflavones and pterocarpane with hepatoprotective activity from the stems of Erycibe expansa. Planta medica. 2004 Dec; 70(12):1201-9. doi: 10.1055/s-2004-835852. [PMID: 15643558]
  • Vibeke M Breinholt, Salka E Rasmussen, Kim Brøsen, Thomas H Friedberg. In vitro metabolism of genistein and tangeretin by human and murine cytochrome P450s. Pharmacology & toxicology. 2003 Jul; 93(1):14-22. doi: 10.1034/j.1600-0773.2003.930102.x. [PMID: 12828569]
  • S E Kulling, D M Honig, M Metzler. Oxidative metabolism of the soy isoflavones daidzein and genistein in humans in vitro and in vivo. Journal of agricultural and food chemistry. 2001 Jun; 49(6):3024-33. doi: 10.1021/jf0012695. [PMID: 11410004]
  • B Min, S R Oh, H K Lee, K Takatsu, I M Chang, K R Min, Y Kim. Sophoricoside analogs as the IL-5 inhibitors from Sophora japonica. Planta medica. 1999 Jun; 65(5):408-12. doi: 10.1055/s-1999-14016. [PMID: 10418325]