Apigenin (BioDeep_00000017281)

Secondary id: BioDeep_00000018745, BioDeep_00000169825, BioDeep_00000402810, BioDeep_00000602558

human metabolite PANOMIX_OTCML-2023 blood metabolite

代谢物信息卡片

(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-((5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid

化学式: C21H18O11 (446.0849078)
中文名称: 芹菜素-7-O-葡萄糖醛酸苷, 芹菜素-7-葡萄糖醛酸
谱图信息: 最多检出来源 Homo sapiens(urine) 31.08%

分子结构信息

SMILES: C1(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(=O)O)O2)=CC2OC(C3C=CC(O)=CC=3)=CC(=O)C=2C(O)=C1
InChI: InChI=1S/C21H18O11/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21-23,25-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1

描述信息

Apigenin 7-glucuronide is a member of flavonoids and a glucosiduronic acid.
Apigenin 7-glucuronide is a natural product found in Galeopsis tetrahit, Galeopsis ladanum, and other organisms with data available.
Apigenin-7-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively.
Apigenin-7-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively.

同义名列表

28 个代谢物同义名

(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-((5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid; BENZOPYRAN-7-YL, .BETA.-D- (8CI) 5-HYDROXY-2-(4-HYDROXYPHENYL)-4-OXO-4H-1-BENZOPYRAN-7-YL .BETA.-D-GLUCOPYRANOSIDURONIC ACID; (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-carboxylic acid; (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid; GLUCOPYRANOSIDURONIC ACID, 5-HYDROXY-2-(P-HYDROXYPHENYL)-4-OXO-4H-1-BENZOPYRAN-7-YL, .BETA.-D-; beta-D-Glucopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl); beta-D-Glucopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl; 4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranuronosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-; Apigenin 7-O-glucuronide, primary pharmaceutical reference standard; Apigenin 7-glucuronide, >=95\\% (LC/MS-ELSD); Apigenin 7-O-beta-D-glucuronopyranoside; apigenin-7-O-betaD-glucuronic acid; Apigenin-7-O-beta-D-glucuronoside; Apigenin 7-O-.beta.-D-glucuronide; Apigenin 7-O-beta-D-glucuronide; apigenin-7-O-beta-D-glucuronide; Apigenin 7-beta-glucuronide; apigenin-7-o-glucuronide; Apigenin 7-O-glucuronide; APIGENIN-7-O-GLUCRONIDE; Apigenin 7-glucuronide; Apigenin-7-glucuronide; UNII-2CQ5KB3CH0; Scutellarin A; MEGxp0_000795; ACon1_001025; 2CQ5KB3CH0; Apigenin

数据库引用编号

10 个数据库交叉引用编号

ChEBI: CHEBI:181620
PubChem: 5319484
HMDB: HMDB0240480
ChEMBL: CHEMBL254213
LipidMAPS: LMPK12110344
MeSH: apigenin-7-O-glucuronide
ChemIDplus: 0029741091
chemspider: 24534146
CAS: 29741-09-1
medchemexpress: HY-N1454

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)

133 个相关的物种来源信息

33090 苦碟子: -
172644 Broussonetia papyrifera: 10.3724/SP.J.1009.2013.00260
99037 Chamaemelum nobile: 10.1515/ZNC-2003-1-202
41507 Centaurea aspera: 10.1016/S0031-9422(00)84956-0
1907919 Scutellaria albida: 10.1055/S-2007-987153
40891 Torilis nodosa: 10.1016/S0031-9422(00)84026-1
79184 Torilis arvensis: 10.1016/S0031-9422(00)84026-1
79189 Torilis tenella: 10.1016/S0031-9422(00)84026-1
1477590 Daphne genkwa: 10.38212/2224-6614.2810
91248 Erigeron annuus:
253483 Fuchsia excorticata: 10.1016/0031-9422(83)80021-1
85206 Fuchsia procumbens: 10.1016/0031-9422(83)80021-1
672825 Meehania urticifolia: 10.1007/S11418-010-0501-Y
233892 Scutellaria indica: 10.1248/CPB.37.794
351340 Centaurea jacea: 10.1016/S0031-9422(01)00066-8
1033235 Centaurea bracteata: 10.1016/S0031-9422(01)00066-8
127999 Tanacetum parthenium:
128002 Tanacetum vulgare: 10.1016/S0031-9422(99)00021-7
53167 Scutellaria alpina: 10.1248/CPB.39.199
268920 Salvia palaestina: 10.1021/NP50030A007
53169 Scutellaria galericulata: 10.1007/BF00567050
751816 Clinopodium umbrosum: 10.1002/JCCS.199300014
59895 Cynara cardunculus var. scolymus: 10.1016/J.FOODCHEM.2005.01.013
41492 Bellis perennis:
241842 Acanthus ebracteatus: 10.1016/S0031-9422(01)00306-5
388205 Penstemon serrulatus: 10.1515/ZNC-1997-7-803
182387 Monarda punctata: 10.1016/J.PHYTOCHEM.2010.08.009
3880 Medicago truncatula: 10.1021/JF063635B
3879 Medicago sativa:
70968 Medicago radiata: 10.1016/0305-1978(82)90048-5
70936 Medicago arabica: 10.1016/0305-1978(82)90048-5
47084 Medicago polymorpha: 10.1016/0305-1978(82)90048-5
268906 Salvia fruticosa: 10.1016/0031-9422(83)80044-2
297478 Onopordum illyricum: 10.1021/NP990098Z
36622 Chaenomeles sinensis:
28509 Glechoma hederacea: 10.1248/CPB.55.346
947972 Aster koraiensis: 10.5012/BKCS.2010.31.01.227
204149 Ocimum tenuiflorum: 10.1021/NP0700164
2867398 Cymbaria daurica: 10.1007/S10600-019-02770-Z
39324 Hyssopus officinalis: 10.1080/10286020.2010.533120
57912 Agrimonia eupatoria: 10.1271/BBB.100200
39352 Origanum vulgare: 10.1002/JCCS.200300153
1081551 Galeopsis pyrenaica: 10.1016/0031-9422(91)83199-U
1000418 Galeopsis tetrahit: 10.1016/0031-9422(91)83199-U
457138 Galeopsis angustifolia: 10.1016/0031-9422(91)83199-U
1030043 Galeopsis ladanum: 10.1016/0031-9422(91)83199-U
1081552 Galeopsis segetum: 10.1016/0031-9422(91)83199-U
457140 Galeopsis speciosa: 10.1016/0031-9422(91)83199-U
457139 Galeopsis pubescens: 10.1016/0031-9422(91)83199-U
572113 Galeopsis bifida: 10.1016/0031-9422(91)83199-U
255872 Picria fel-terrae: 10.1016/S0031-9422(99)00242-3
255872 Picria felterrae: 10.1016/S0031-9422(99)00242-3
1620142 Lycopus virginicus: 10.1055/S-2006-958111
1611021 Meehania fargesii: 10.1248/CPB.58.696
24051 Strobilanthes: 10.1248/CPB.39.927
4151 Antirrhinum majus:
1818589 Fernandoa adenophylla: 10.1016/S0031-9422(01)00212-6
572133 Phlomoides tuberosa: 10.1007/BF00563331
328098 Acanthus ilicifolius: 10.1016/S0031-9422(00)00362-9
185774 Jacaranda mimosifolia: 10.21608/BFSA.2002.65695
326831 Pedicularis longiflora: 10.1055/S-2006-959387
165318 Veronica spicata: 10.1007/BF00569605
680227 Millingtonia hortensis: 10.1016/0031-9422(95)00206-M
244311 Erigeron breviscapus: 10.1016/S0021-9673(01)01111-6
99072 Leucanthemum vulgare: 10.1007/BF00576106
172644 Broussonetia papyrifera: 10.3724/SP.J.1009.2013.00260
99037 Chamaemelum nobile: 10.1515/ZNC-2003-1-202
41507 Centaurea aspera: 10.1016/S0031-9422(00)84956-0
1907919 Scutellaria albida: 10.1055/S-2007-987153
40891 Torilis nodosa: 10.1016/S0031-9422(00)84026-1
79184 Torilis arvensis: 10.1016/S0031-9422(00)84026-1
79189 Torilis tenella: 10.1016/S0031-9422(00)84026-1
1477590 Daphne genkwa: 10.38212/2224-6614.2810
91248 Erigeron annuus:
253483 Fuchsia excorticata: 10.1016/0031-9422(83)80021-1
85206 Fuchsia procumbens: 10.1016/0031-9422(83)80021-1
672825 Meehania urticifolia: 10.1007/S11418-010-0501-Y
233892 Scutellaria indica: 10.1248/CPB.37.794
351340 Centaurea jacea: 10.1016/S0031-9422(01)00066-8
1033235 Centaurea bracteata: 10.1016/S0031-9422(01)00066-8
127999 Tanacetum parthenium:
128002 Tanacetum vulgare: 10.1016/S0031-9422(99)00021-7
53167 Scutellaria alpina: 10.1248/CPB.39.199
268920 Salvia palaestina: 10.1021/NP50030A007
53169 Scutellaria galericulata: 10.1007/BF00567050
751816 Clinopodium umbrosum: 10.1002/JCCS.199300014
59895 Cynara cardunculus var. scolymus: 10.1016/J.FOODCHEM.2005.01.013
41492 Bellis perennis:
241842 Acanthus ebracteatus: 10.1016/S0031-9422(01)00306-5
388205 Penstemon serrulatus: 10.1515/ZNC-1997-7-803
182387 Monarda punctata: 10.1016/J.PHYTOCHEM.2010.08.009
3880 Medicago truncatula: 10.1021/JF063635B
3879 Medicago sativa:
70968 Medicago radiata: 10.1016/0305-1978(82)90048-5
70936 Medicago arabica: 10.1016/0305-1978(82)90048-5
47084 Medicago polymorpha: 10.1016/0305-1978(82)90048-5
268906 Salvia fruticosa: 10.1016/0031-9422(83)80044-2
297478 Onopordum illyricum: 10.1021/NP990098Z
36622 Chaenomeles sinensis:
28509 Glechoma hederacea: 10.1248/CPB.55.346
947972 Aster koraiensis: 10.5012/BKCS.2010.31.01.227
204149 Ocimum tenuiflorum: 10.1021/NP0700164
2867398 Cymbaria daurica: 10.1007/S10600-019-02770-Z
39324 Hyssopus officinalis: 10.1080/10286020.2010.533120
57912 Agrimonia eupatoria: 10.1271/BBB.100200
39352 Origanum vulgare: 10.1002/JCCS.200300153
1081551 Galeopsis pyrenaica: 10.1016/0031-9422(91)83199-U
1000418 Galeopsis tetrahit: 10.1016/0031-9422(91)83199-U
457138 Galeopsis angustifolia: 10.1016/0031-9422(91)83199-U
1030043 Galeopsis ladanum: 10.1016/0031-9422(91)83199-U
1081552 Galeopsis segetum: 10.1016/0031-9422(91)83199-U
457140 Galeopsis speciosa: 10.1016/0031-9422(91)83199-U
457139 Galeopsis pubescens: 10.1016/0031-9422(91)83199-U
572113 Galeopsis bifida: 10.1016/0031-9422(91)83199-U
255872 Picria fel-terrae: 10.1016/S0031-9422(99)00242-3
255872 Picria felterrae: 10.1016/S0031-9422(99)00242-3
1620142 Lycopus virginicus: 10.1055/S-2006-958111
1611021 Meehania fargesii: 10.1248/CPB.58.696
24051 Strobilanthes: 10.1248/CPB.39.927
4151 Antirrhinum majus:
1818589 Fernandoa adenophylla: 10.1016/S0031-9422(01)00212-6
572133 Phlomoides tuberosa: 10.1007/BF00563331
328098 Acanthus ilicifolius: 10.1016/S0031-9422(00)00362-9
185774 Jacaranda mimosifolia: 10.21608/BFSA.2002.65695
326831 Pedicularis longiflora: 10.1055/S-2006-959387
165318 Veronica spicata: 10.1007/BF00569605
680227 Millingtonia hortensis: 10.1016/0031-9422(95)00206-M
244311 Erigeron breviscapus: 10.1016/S0021-9673(01)01111-6
99072 Leucanthemum vulgare: 10.1007/BF00576106
9606 Homo sapiens: -
536997 Callicarpa macrophylla Vahl: -
92921 Silybum marianum (L.) Gaertn.: -
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

Jin Seok Lee, Yu Ran Nam, Hyun Jong Kim, Woo Kyung Kim. Quantification and Validation of an HPLC Method for Low Concentrations of Apigenin-7-O-Glucuronide in Agrimonia pilosa Aqueous Ethanol Extract Topical Cream by Liquid-Liquid Extraction. Molecules (Basel, Switzerland). 2023 Jan; 28(2):. doi: 10.3390/molecules28020713. [PMID: 36677776]
Jun Gu Kim, Jin Woo Lee, Thi Phuong Linh Le, Jae Sang Han, Yong Beom Cho, Haeun Kwon, Dongho Lee, Mi Kyeong Lee, Bang Yeon Hwang. Sesquiterpenoids from Chrysanthemum indicum with Inhibitory Effects on NO Production. Journal of natural products. 2021 03; 84(3):562-569. doi: 10.1021/acs.jnatprod.0c01121. [PMID: 33667099]
Ankur Kumar Tanwar, Neha Dhiman, Amit Kumar, Vikas Jaitak. Engagement of phytoestrogens in breast cancer suppression: Structural classification and mechanistic approach. European journal of medicinal chemistry. 2021 Mar; 213(?):113037. doi: 10.1016/j.ejmech.2020.113037. [PMID: 33257172]
Jinxin Shi, Chengpeng Sun, Huilian Huang, Wenhui Lin, Jian Gao, Yanhe Lin, Zhanjun Zhang, Xiaokui Huo, Xiangge Tian, Zhenlong Yu, Baojing Zhang, Xiaochi Ma. β-Glucuronidase- and OATP2B1-mediated drug interaction of scutellarin in Dengzhan Xixin Injection: A formulation aspect. Drug development research. 2020 08; 81(5):609-619. doi: 10.1002/ddr.21661. [PMID: 32220026]
Xiaonan Liu, Jian Cheng, Guanghui Zhang, Wentao Ding, Lijin Duan, Jing Yang, Ling Kui, Xiaozhi Cheng, Jiangxing Ruan, Wei Fan, Junwen Chen, Guangqiang Long, Yan Zhao, Jing Cai, Wen Wang, Yanhe Ma, Yang Dong, Shengchao Yang, Huifeng Jiang. Engineering yeast for the production of breviscapine by genomic analysis and synthetic biology approaches. Nature communications. 2018 01; 9(1):448. doi: 10.1038/s41467-018-02883-z. [PMID: 29386648]
Rudi Hendra, Paul A Keller. Phytochemical Studies on Two Australian Anigozanthos Plant Species. Journal of natural products. 2017 07; 80(7):2141-2145. doi: 10.1021/acs.jnatprod.7b00063. [PMID: 28682615]
Jia Hou, Jian-Chun Hu, Yue-Ting Li, Ting Liu, Yong Huang, Ai-Min Wang. [Absorption characteristics of 5 components of Xinshao extract in Caco-2 cells]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2016 Jun; 41(11):2137-2143. doi: 10.4268/cjcmm20161126. [PMID: 28901113]
Weicheng Hu, Xinfeng Wang, Lei Wu, Ting Shen, Lilian Ji, Xihong Zhao, Chuan-Ling Si, Yunyao Jiang, Gongcheng Wang. Apigenin-7-O-β-D-glucuronide inhibits LPS-induced inflammation through the inactivation of AP-1 and MAPK signaling pathways in RAW 264.7 macrophages and protects mice against endotoxin shock. Food & function. 2016 Feb; 7(2):1002-13. doi: 10.1039/c5fo01212k. [PMID: 26750400]
Alessandro Venditti, Laura Guarcini, Armandodoriano Bianco, Sergio Rosselli, Maurizio Bruno, Felice Senatore. Phytochemical analysis of Achillea ligustica All. from Lipari Island (Aeolian Islands). Natural product research. 2016; 30(8):912-9. doi: 10.1080/14786419.2015.1079188. [PMID: 26327332]
Carla Pereira, Lillian Barros, Ana Maria Carvalho, Celestino Santos-Buelga, Isabel C F R Ferreira. Infusions of artichoke and milk thistle represent a good source of phenolic acids and flavonoids. Food & function. 2015 Jan; 6(1):56-62. doi: 10.1039/c4fo00834k. [PMID: 25367590]
Nabila Zaabat, Anne-Emmanuelle Hay, Serge Michalet, Nicole Darbour, Christine Bayet, Inès Skandrani, Leila Chekir-Ghedira, Salah Akkal, Marie-Geneviève Dijoux-Franca. Antioxidant and antigenotoxic properties of compounds isolated from Marrubium deserti de Noé. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Dec; 49(12):3328-35. doi: 10.1016/j.fct.2011.08.026. [PMID: 21924316]
Ozlem Baris, Mehmet Karadayi, Derya Yanmis, Zuhal Guvenalp, Tugba Bal, Medine Gulluce. Isolation of 3 flavonoids from Mentha longifolia (L.) Hudson subsp. longifolia and determination of their genotoxic potentials by using the E. coli WP2 test system. Journal of food science. 2011 Nov; 76(9):T212-7. doi: 10.1111/j.1750-3841.2011.02405.x. [PMID: 22416730]
Zhifeng Zhang, Wenxia Sun, Pei Luo, Liping Wu, Limin Ye, Hao Zhang. Simultaneous determination of five main active constituents of Erigeron multiradiatus by HPLC-DAD-MS. Journal of pharmaceutical and biomedical analysis. 2008 Nov; 48(3):980-5. doi: 10.1016/j.jpba.2008.06.010. [PMID: 18678455]
Pei Luo, Zhifeng Zhang, Tao Yi, Hao Zhang, Xinfu Liu, Zhengji Mo. Anti-inflammatory activity of the extracts and fractions from Erigeron multiradiatus through bioassay-guided procedures. Journal of ethnopharmacology. 2008 Sep; 119(2):232-7. doi: 10.1016/j.jep.2008.06.035. [PMID: 18678238]
Prasoon Gupta, Dinesh Kumar Yadav, Kiran Babu Siripurapu, Guatam Palit, Rakesh Maurya. Constituents of Ocimum sanctum with antistress activity. Journal of natural products. 2007 Sep; 70(9):1410-6. doi: 10.1021/np0700164. [PMID: 17850106]
Y S Min, S H Yim, K L Bai, H J Choi, J H Jeong, H J Song, S Y Park, I Ham, W K Whang, U D Sohn. The effects of apigenin-7-O-beta-D-glucuronopyranoside on reflux oesophagitis and gastritis in rats. Autonomic & autacoid pharmacology. 2005 Jul; 25(3):85-91. doi: 10.1111/j.1474-8673.2005.00332.x. [PMID: 15955027]
Ji Sun Lee, Hyoung Ja Kim, Yong Sup Lee. A new anti-HIV flavonoid glucuronide from Chrysanthemum morifolium. Planta medica. 2003 Sep; 69(9):859-61. doi: 10.1055/s-2003-43207. [PMID: 14598216]
Gerd Vanhoenacker, Philippe Van Rompaey, Denis De Keukeleire, Pat Sandra. Chemotaxonomic features associated with flavonoids of cannabinoid-free cannabis (Cannabis sativa subsp. sativa L.) in relation to hops (Humulus lupulus L.). Natural product letters. 2002 Feb; 16(1):57-63. doi: 10.1080/1057563029001/4863. [PMID: 11942684]