7,4'-Dihydroxyflavone (BioDeep_00000003616)

human metabolite PANOMIX_OTCML-2023 blood metabolite

代谢物信息卡片

7-Hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

化学式: C15H10O4 (254.057906)
中文名称: 7,4-二羟基黄酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(ccc2c(c1)oc(cc2=O)c1ccc(cc1)O)O
InChI: InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-8,16-17H

描述信息

7,4-dihydroxyflavone, also known as 7-hydroxy-2-(4-hydroxyphenyl)-4h-chromen-4-one, is a member of the class of compounds known as flavones. Flavones are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, 7,4-dihydroxyflavone is considered to be a flavonoid lipid molecule. 7,4-dihydroxyflavone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 7,4-dihydroxyflavone can be found in alfalfa, broad bean, and fenugreek, which makes 7,4-dihydroxyflavone a potential biomarker for the consumption of these food products. Like many other flavonoids, 4,7-dihydroxyflavone has been found to possess activity at the opioid receptors. Specifically, it acts as an antagonist of the μ-opioid receptor and, with lower affinity, of the κ- and δ-opioid receptors .
7,4'-Dihydroxyflavone (7,4'-DHF) is a flavonoid isolated from Glycyrrhiza uralensis, the eotaxin/CCL11 inhibitor, has the ability to consistently suppress eotaxin production and prevent dexamethasone (Dex)‐paradoxical adverse effects on eotaxin production[1]. 7,4'-Dihydroxyflavone (7,4'-DHF) inhibits MUC5AC gene expression, mucus production and secretion via regulation of NF-κB, STAT6 and HDAC2. 7,4'-Dihydroxyflavone (7,4'-DHF) decreases phorbol 12-myristate 13-acetate (PMA) stimulated NCI-H292 human airway epithelial cell MUC5AC gene expression and mucus production with IC50 value of 1.4 μM[1].
7,4'-Dihydroxyflavone (7,4'-DHF) is a flavonoid isolated from Glycyrrhiza uralensis, the eotaxin/CCL11 inhibitor, has the ability to consistently suppress eotaxin production and prevent dexamethasone (Dex)‐paradoxical adverse effects on eotaxin production[1]. 7,4'-Dihydroxyflavone (7,4'-DHF) inhibits MUC5AC gene expression, mucus production and secretion via regulation of NF-κB, STAT6 and HDAC2. 7,4'-Dihydroxyflavone (7,4'-DHF) decreases phorbol 12-myristate 13-acetate (PMA) stimulated NCI-H292 human airway epithelial cell MUC5AC gene expression and mucus production with IC50 value of 1.4 μM[1].

同义名列表

6 个代谢物同义名

7-Hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one; 7,4-dihydroxyflavone 7-O-glucoside; 4,7-Dihydroxyflavone; 7,4-Dihydroxyflavone; 7,4-DHF; 7,4'-Dihydroxyflavone

数据库引用编号

18 个数据库交叉引用编号

ChEBI: CHEBI:29503
KEGG: C12123
PubChem: 5282073
HMDB: HMDB0247290
Metlin: METLIN48471
ChEMBL: CHEMBL294878
Wikipedia: 4,7-Dihydroxyflavone
LipidMAPS: LMPK12110035
KNApSAcK: C00003800
foodb: FDB001536
chemspider: 4445298
CAS: 2196-14-7
PMhub: MS000010416
PubChem: 14270
3DMET: B04424
NIKKAJI: J78.045F
RefMet: 7,4'-Dihydroxyflavone
medchemexpress: HY-N2609

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)

89 个相关的物种来源信息

557660 Inula salsoloides: 10.1002/HLCA.201000195
3906 Vicia faba: 10.1021/JF00002A006
3900 Trifolium subterraneum: 10.1016/S0031-9422(00)85667-8
3899 Trifolium repens: 10.1016/S0031-9422(00)85667-8
2715301 Oxytropis trichophysa: 10.1007/BF00630449
489316 Entada phaseoloides: 10.1002/CBDV.201100002
3879 Medicago sativa: 10.1016/0031-9422(93)85025-M
3880 Medicago truncatula:
70607 Sophora microphylla:
76398 Sophora prostrata:
171561 Sophora chrysophylla:
1196212 Sophora viciifolia:
49839 Sophora davidii:
1210111 Trigonella maritima: 10.1016/0305-1978(82)90048-5
390135 Trigonella anguina: 10.1016/0305-1978(82)90048-5
78534 Trigonella foenum-graecum: 10.1016/0305-1978(82)90048-5
70968 Medicago radiata: 10.1016/0305-1978(82)90048-5
200964 Trigonella coerulescens: 10.1016/0305-1978(82)90048-5
119386 Trigonella spicata: 10.1016/0305-1978(82)90048-5
1142948 Dracaena cinnabari: 10.1016/0031-9422(94)00738-F
74614 Glycyrrhiza inflata:
372983 Glycyrrhiza eurycarpa:
46348 Glycyrrhiza echinata:
74859 Glycyrrhiza pallidiflora:
49827 Glycyrrhiza glabra:
74613 Glycyrrhiza uralensis:
912971 Glycyrrhiza yunnanensis:
3830 Crotalaria pallida: 10.1016/J.BMCL.2003.11.074
149633 Baptisia australis:
1969223 Baptisia megacarpa:
1871516 Baptisia perfoliata:
1969224 Baptisia simplicifolia:
1969221 Baptisia lanceolata:
313912 Baptisia bracteata:
1969220 Baptisia calycosa:
313914 Baptisia sphaerocarpa:
313913 Baptisia cinerea:
1969222 Baptisia lecontei:
1835378 Brosimum acutifolium:
114325 Thermopsis villosa: 10.1016/S0031-9422(00)88458-7
2805045 Thermopsis mollis: 10.1016/S0031-9422(00)88458-7
114322 Thermopsis macrophylla: 10.1016/S0031-9422(00)88458-7
61122 Thermopsis rhombifolia: 10.1016/S0031-9422(00)88458-7
557660 Inula salsoloides: 10.1002/HLCA.201000195
3906 Vicia faba: 10.1021/JF00002A006
3900 Trifolium subterraneum: 10.1016/S0031-9422(00)85667-8
3899 Trifolium repens: 10.1016/S0031-9422(00)85667-8
2715301 Oxytropis trichophysa: 10.1007/BF00630449
489316 Entada phaseoloides: 10.1002/CBDV.201100002
3879 Medicago sativa: 10.1016/0031-9422(93)85025-M
3880 Medicago truncatula:
70607 Sophora microphylla:
76398 Sophora prostrata:
171561 Sophora chrysophylla:
1196212 Sophora viciifolia:
49839 Sophora davidii:
1210111 Trigonella maritima: 10.1016/0305-1978(82)90048-5
390135 Trigonella anguina: 10.1016/0305-1978(82)90048-5
78534 Trigonella foenum-graecum: 10.1016/0305-1978(82)90048-5
70968 Medicago radiata: 10.1016/0305-1978(82)90048-5
200964 Trigonella coerulescens: 10.1016/0305-1978(82)90048-5
119386 Trigonella spicata: 10.1016/0305-1978(82)90048-5
1142948 Dracaena cinnabari: 10.1016/0031-9422(94)00738-F
74614 Glycyrrhiza inflata:
372983 Glycyrrhiza eurycarpa:
46348 Glycyrrhiza echinata:
74859 Glycyrrhiza pallidiflora:
49827 Glycyrrhiza glabra:
74613 Glycyrrhiza uralensis:
912971 Glycyrrhiza yunnanensis:
3830 Crotalaria pallida: 10.1016/J.BMCL.2003.11.074
149633 Baptisia australis:
1969223 Baptisia megacarpa:
1871516 Baptisia perfoliata:
1969224 Baptisia simplicifolia:
1969221 Baptisia lanceolata:
313912 Baptisia bracteata:
1969220 Baptisia calycosa:
313914 Baptisia sphaerocarpa:
313913 Baptisia cinerea:
1969222 Baptisia lecontei:
1835378 Brosimum acutifolium:
114325 Thermopsis villosa: 10.1016/S0031-9422(00)88458-7
2805045 Thermopsis mollis: 10.1016/S0031-9422(00)88458-7
114322 Thermopsis macrophylla: 10.1016/S0031-9422(00)88458-7
61122 Thermopsis rhombifolia: 10.1016/S0031-9422(00)88458-7
9606 Homo sapiens: -
1196212 Sophora viciifolia: -
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

Safa M Shams Eldin, Mohamed M Radwan, Amira S Wanas, Abdel-Azim M Habib, Fahima F Kassem, Hala M Hammoda, Shabana I Khan, Michael L Klein, Khaled M Elokely, Mahmoud A ElSohly. Bioactivity-Guided Isolation of Potential Antidiabetic and Antihyperlipidemic Compounds from Trigonella stellata. Journal of natural products. 2018 05; 81(5):1154-1161. doi: 10.1021/acs.jnatprod.7b00707. [PMID: 29676912]
Yan Lin, Yi Kuang, Kai Li, Shuang Wang, Shuai Ji, Kuan Chen, Wei Song, Xue Qiao, Min Ye. Nrf2 activators from Glycyrrhiza inflata and their hepatoprotective activities against CCl4-induced liver injury in mice. Bioorganic & medicinal chemistry. 2017 10; 25(20):5522-5530. doi: 10.1016/j.bmc.2017.08.018. [PMID: 28835349]
Yan Lin, Yi Kuang, Kai Li, Shuang Wang, Wei Song, Xue Qiao, Gulnar Sabir, Min Ye. Screening for bioactive natural products from a 67-compound library of Glycyrrhiza inflata. Bioorganic & medicinal chemistry. 2017 07; 25(14):3706-3713. doi: 10.1016/j.bmc.2017.05.009. [PMID: 28522265]
Jiachun Li, Dongpo Li, Youzhi Pan, Jun-Hua Hu, Wenzhe Huang, Zhen-Zhong Wang, Wei Xiao, Yu Wang. Simultaneous determination of ten bioactive constituents of Sanjie Zhentong Capsule in rat plasma by ultra-high-performance liquid chromatography tandem mass spectrometry and its application to a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Jun; 1054(?):20-26. doi: 10.1016/j.jchromb.2017.03.001. [PMID: 28415020]
Yelin Kang, Bong-Gyu Kim, Sunghoon Kim, Youngshim Lee, Youngdae Yoon. Inhibitory potential of flavonoids on PtdIns(3,4,5)P3 binding with the phosphoinositide-dependent kinase 1 pleckstrin homology domain. Bioorganic & medicinal chemistry letters. 2017 02; 27(3):420-426. doi: 10.1016/j.bmcl.2016.12.051. [PMID: 28049590]
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]
Yun Li, Wei Xiao, Jianping Qin, Ying Guo, Qianqian Zhu. [Simultaneous determination of five active components in resina draconis and its extract by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Apr; 37(7):929-33. doi: . [PMID: 22792791]
Ao-Xue Wang, Ying Hu, Hui-Xin Liu, Xiao-Yi Qi, Yong Liu, Cai-Xia Tu, Ling Yang. C5-hydroxylation of liquiritigenin is catalyzed selectively by CYP1A2. Xenobiotica; the fate of foreign compounds in biological systems. 2011 May; 41(5):349-57. doi: 10.3109/00498254.2010.546014. [PMID: 21210738]
Judith Fliegmann, Katarina Furtwängler, Georg Malterer, Corrado Cantarello, Göde Schüler, Jürgen Ebel, Axel Mithöfer. Flavone synthase II (CYP93B16) from soybean (Glycine max L.). Phytochemistry. 2010 Apr; 71(5-6):508-14. doi: 10.1016/j.phytochem.2010.01.007. [PMID: 20132953]
Bolleddula Jayaprakasam, Srinivasulu Doddaga, Rong Wang, Daniel Holmes, Joseph Goldfarb, Xiu-Min Li. Licorice flavonoids inhibit eotaxin-1 secretion by human fetal lung fibroblasts in vitro. Journal of agricultural and food chemistry. 2009 Feb; 57(3):820-5. doi: 10.1021/jf802601j. [PMID: 19132888]
Juan Zhang, Senthil Subramanian, Gary Stacey, Oliver Yu. Flavones and flavonols play distinct critical roles during nodulation of Medicago truncatula by Sinorhizobium meliloti. The Plant journal : for cell and molecular biology. 2009 Jan; 57(1):171-83. doi: 10.1111/j.1365-313x.2008.03676.x. [PMID: 18786000]
René Kupfer, Leah Swanson, Sylvia Chow, Richard E Staub, Yan Ling Zhang, Isaac Cohen, Uwe Christians. Oxidative in vitro metabolism of liquiritigenin, a bioactive compound isolated from the Chinese herbal selective estrogen beta-receptor agonist MF101. Drug metabolism and disposition: the biological fate of chemicals. 2008 Nov; 36(11):2261-9. doi: 10.1124/dmd.108.021402. [PMID: 18669586]
Xiang Li, Zhi Liu, Xin-feng Zhang, Li-juan Wang, Yi-nan Zheng, Chang-chun Yuan, Guang-zhi Sun. Isolation and characterization of phenolic compounds from the leaves of Salix matsudana. Molecules (Basel, Switzerland). 2008 Aug; 13(8):1530-7. doi: 10.3390/molecules13081530. [PMID: 18794770]
Peter L Katavic, Kenneth Lamb, Hernan Navarro, Thomas E Prisinzano. Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships. Journal of natural products. 2007 Aug; 70(8):1278-82. doi: 10.1021/np070194x. [PMID: 17685652]
Q-A Zheng, Y-J Zhang, C-R Yang. A new meta-homoisoflavane from the fresh stems of dracaena cochinchinensis. Journal of Asian natural products research. 2006 Sep; 8(6):571-7. doi: 10.1080/1028602042000204126. [PMID: 16931435]
Hun Sung Yoo, Ji Suk Lee, Chul Young Kim, Jinwoong Kim. Flavonoids of Crotalaria sessiliflora. Archives of pharmacal research. 2004 May; 27(5):544-6. doi: 10.1007/bf02980129. [PMID: 15202561]
Horng-Huey Ko, Jing-Ru Weng, Lo-Ti Tsao, Ming-Hong Yen, Jih-Pyang Wang, Chun-Nan Lin. Anti-inflammatory flavonoids and pterocarpanoid from Crotalaria pallida and C. assamica. Bioorganic & medicinal chemistry letters. 2004 Feb; 14(4):1011-4. doi: 10.1016/j.bmcl.2003.11.074. [PMID: 15013012]
Katja Schwalm, Roni Aloni, Markus Langhans, Werner Heller, Susanne Stich, Cornelia I Ullrich. Flavonoid-related regulation of auxin accumulation in Agrobacterium tumefaciens-induced plant tumors. Planta. 2003 Dec; 218(2):163-78. doi: 10.1007/s00425-003-1104-6. [PMID: 14523649]
Jeong An Park, Hyoung Ja Kim, Changbae Jin, Kyung-Tae Lee, Yong Sup Lee. A new pterocarpan, (-)-maackiain sulfate, from the roots of Sophora subprostrata. Archives of pharmacal research. 2003 Dec; 26(12):1009-13. doi: 10.1007/bf02994750. [PMID: 14723332]
U Mathesius. Flavonoids induced in cells undergoing nodule organogenesis in white clover are regulators of auxin breakdown by peroxidase. Journal of experimental botany. 2001 Mar; 52(Spec Issue):419-26. doi: 10.1093/jexbot/52.suppl_1.419. [PMID: 11326048]
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]
G Lewin, Y Rolland, S Privat, C Breugnot, A Lenaers, J P Vilaine, J P Baltaze, J Poisson. Synthesis and evaluation of 3',5'-di-tert-butyl-4'-hydroxyflavones as potential inhibitors of low density lipoprotein (LDL) oxidation. Journal of natural products. 1995 Dec; 58(12):1840-7. doi: 10.1021/np50126a006. [PMID: 8691205]
M L Braysher. The excretion of hyperosmotic urine and other aspects of the electrolyte balance of the lizard Amphibolurus maculosus. Comparative biochemistry and physiology. A, Comparative physiology. 1976; 54(3):341-5. doi: 10.1016/s0300-9629(76)80123-5. [PMID: 5226]