(-)-Epicatechin 3-O-gallate (BioDeep_00000017213)

Secondary id: BioDeep_00000033794, BioDeep_00000267569, BioDeep_00000402890, BioDeep_00000406553, BioDeep_00000407825, BioDeep_00000864020, BioDeep_00000865240

human metabolite PANOMIX_OTCML-2023 blood metabolite

代谢物信息卡片

Benzoic acid, 3,4,5-trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester, (2R-cis)-

化学式: C22H18O10 (442.0899928)
中文名称: (-)-表儿茶素没食子酸酯, 表儿茶素没食子酸酯, 表儿茶精没食子酸酯, 表儿茶素没食子酸酯
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.06%

分子结构信息

SMILES: c1(cc(c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(c(c(c1)O)O)O)c1ccc(c(c1)O)O)O)O
InChI: InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1

描述信息

(-)-epicatechin-3-O-gallate is a gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida. It has a role as a metabolite, an EC 3.2.1.1 (alpha-amylase) inhibitor and an EC 3.2.1.20 (alpha-glucosidase) inhibitor. It is a catechin, a gallate ester and a polyphenol. It is functionally related to a (-)-epicatechin and a gallic acid.
(-)-Epicatechin gallate is a natural product found in Scurrula atropurpurea, Acacia omalophylla, and other organisms with data available.
Isolated from tea and numerous other plant subspecies inc. rhubarb and grapes. Epicatechin 3-gallate is found in many foods, some of which are cucumber, muskmelon, black raspberry, and cashew nut.
A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.
(-)-Epicatechin 3-O-gallate is found in almond. (-)-Epicatechin 3-O-gallate is isolated from tea and numerous other plant species including rhubarb and grapes.
D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors
D020011 - Protective Agents > D000975 - Antioxidants
D000970 - Antineoplastic Agents
(-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.
(-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.
(-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.
(-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.

同义名列表

61 个代谢物同义名

数据库引用编号

15 个数据库交叉引用编号

ChEBI: CHEBI:70255
PubChem: 107905
HMDB: HMDB0037944
ChEMBL: CHEMBL36327
Wikipedia: Epicatechin_gallate
LipidMAPS: LMPK12020090
MeSH: epicatechin gallate
ChemIDplus: 0001257085
KNApSAcK: C00008866
foodb: FDB017114
chemspider: 97034
CAS: 1257-08-5
medchemexpress: HY-N0002
MetaboLights: MTBLC70255
KEGG: C22594

分类词条

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

galloylated catechin biosynthesis: (-)-epicatechin + 1-O-galloyl-β-D-glucose ⟶ (-)-epicatechin-3-O-gallate + D-glucopyranose

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

galloylated catechin biosynthesis: UDP-α-D-glucose + gallate ⟶ 1-O-galloyl-β-D-glucose + UDP
galloylated catechin biosynthesis: (-)-epicatechin + 1-O-galloyl-β-D-glucose ⟶ (-)-epicatechin-3-O-gallate + D-glucopyranose

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

224 个相关的物种来源信息

33090 茶: -
880079 Rhododendron dauricum: 10.1007/S10600-010-9649-7
4329 Macadamia: 10.1021/JF061478A
3818 Arachis hypogaea: 10.1021/JF061478A
3625 Actinidia chinensis:
3435 Persea americana:
13450 Corylus: 10.1021/JF061478A
4640 Musa:
4615 Ananas comosus:
32201 Carya illinoinensis: 10.1021/JF061478A
55513 Pistacia vera: 10.1021/JF061478A
3755 Prunus dulcis: 10.1021/JF061478A
3645 Bertholletia excelsa: 10.1021/JF061478A
3337 Pinus: 10.1021/JF061478A
171929 Anacardium occidentale: 10.1021/JF061478A
51240 Juglans regia: 10.1021/JF061478A
40716 Paeonia obovata: 10.1248/CPB.48.201
29760 Vitis vinifera:
4442 Camellia sinensis:
3708 Brassica napus: 10.3389/FNUT.2022.822033
4530 Oryza sativa: 10.3390/MOLECULES16031917
119949 Myrtus communis: 10.1007/BF02467181
1407748 Camellia crassicolumna: 10.1021/JF802974M
2516462 Archidendron bubalinum: 10.1016/0031-9422(92)80375-O
666566 Rhodiola semenovii:
289766 Sclerocarya birrea: 10.1021/JF030374M
2726413 Sedum crassularia: 10.1016/0031-9422(93)85416-O
28519 Sedum sediforme: 10.1016/0031-9422(93)85416-O
508984 Schnella guianensis: 10.1016/0031-9422(88)80455-2
2291126 Fagopyrum acutatum: 10.1016/J.JEP.2005.02.029
516549 Fagopyrum dibotrys: 10.1016/J.JEP.2005.02.029
35925 Diospyros kaki:
171204 Acer barbinerve: 10.1007/S10600-011-0016-0
39993 Terminalia catappa: 10.1002/JCCS.199900085
296036 Phyllanthus emblica: 10.1021/NP000135I
296034 Phyllanthus niruri: 10.1016/0031-9422(92)80352-F
1387640 Mezoneuron benthamianum: 10.1076/1388-0209(200009)3841-AFT284
327901 Detarium microcarpum: 10.1016/0166-3542(93)90095-Z
1173659 Acacia omalophylla: 10.1016/S0031-9422(00)85959-2
1174874 Acacia pubifolia: 10.1016/S0031-9422(00)85959-2
139006 Acacia calamifolia: 10.1016/S0031-9422(00)85959-2
694541 Acacia doratoxylon: 10.1016/S0031-9422(00)85959-2
204988 Acacia adunca: 10.1016/S0031-9422(00)85959-2
1174755 Acacia clunies-rossiae: 10.1016/S0031-9422(00)85959-2
139013 Acacia oswaldii: 10.1016/S0031-9422(00)85959-2
138511 Acacia aulacocarpa: 10.1016/S0031-9422(00)85959-2
880440 Acacia pycnantha: 10.1016/S0031-9422(00)85959-2
1174758 Acacia complanata: 10.1016/S0031-9422(00)85959-2
1378425 Acacia trineura: 10.1016/S0031-9422(00)85959-2
224085 Acacia mangium: 10.1016/S0031-9422(00)85959-2
1174742 Acacia binervia: 10.1016/S0031-9422(00)85959-2
98504 Matricaria chamomilla: 10.1111/J.1365-2621.2005.TB08304.X
4400 Liquidambar styraciflua: 10.1016/0031-9422(93)85229-K
260143 Syzygium samarangense: 10.1248/CPB.40.2671
326968 Ziziphus jujuba: 10.1007/BF02291535
38942 Quercus robur: 10.1007/BF02249631
3760 Prunus persica:
1146880 Scurrula atropurpurea: 10.1248/CPB.51.343
41241 Rumex acetosa: 10.1016/J.FITOTE.2009.08.015
148713 Parapiptadenia rigida: 10.1021/NP100523S
29747 Mallotus japonicus: 10.1016/S0031-9422(00)98001-4
32239 Dasiphora fruticosa: 10.1007/BF00565058
208863 Myriophyllum aquaticum: 10.1021/NP50066A004
318062 Euphorbia hirta:
3888 Pisum sativum: 10.1021/JF000549H
36596 Prunus armeniaca: 10.1021/JF000549H
4236 Lactuca sativa: 10.1021/JF000549H
3758 Prunus domestica: 10.1021/JF000549H
42229 Prunus avium: 10.1021/JF000549H
3663 Cucurbita pepo: 10.1021/JF000549H
3494 Ficus carica: 10.1021/JF000549H
3750 Malus domestica: 10.1021/JF000549H
283210 Malus pumila: 10.1021/JF000549H
36609 Cydonia: 10.1021/JF000549H
4565 Triticum aestivum: 10.1021/JF000549H
3746 Fragaria: 10.1021/JF000549H
4039 Daucus carota: 10.1021/JF000549H
36616 Mespilus germanica: 10.1021/JF000549H
3827 Cicer arietinum: 10.1021/JF000549H
3885 Phaseolus vulgaris: 10.1021/JF000549H
21019 Castanea: 10.1021/JF000549H
3864 Lens culinaris: 10.1021/JF000549H
3906 Vicia faba: 10.1021/JF000549H
23211 Pyrus communis: 10.1021/JF000549H
175228 Ribes rubrum: 10.1021/JF000549H
23216 Rubus: 10.1021/JF000549H
301862 Annona reticulata: 10.1021/JF000549H
4072 Capsicum annuum: 10.1021/JF000549H
4111 Solanum melongena: 10.1021/JF000549H
22663 Punica granatum: 10.1021/JF000549H
4081 Solanum lycopersicum: 10.1021/JF000549H
229543 Hibiscus cannabinus: 10.1007/BF00574392
138017 Senegalia catechu: 10.1021/JF0531499
875646 Senegalia polyacantha: 10.1021/JF0531499
28974 Averrhoa carambola: 10.1007/S11418-008-0239-Y
29780 Mangifera indica: 10.1248/CPB.32.2676
122832 Platanus orientalis: 10.1023/B:CONC.0000025479.07578.5D
3617 Fagopyrum esculentum:
642531 Pyrola incarnata: 10.1016/0031-9422(89)80060-3
13442 Coffea: 10.1021/JF000026+
889930 Parkia biglobosa: 10.1016/S0367-326X(99)00137-9
46901 Persicaria hydropiper: 10.1016/S0031-9422(98)00426-9
255348 Rhus typhina: 10.1007/BF00633406
714442 Ampelopsis japonica: 10.1007/S11418-006-0119-2
91113 Orostachys fimbriata: 10.1016/J.FITOTE.2008.10.003
137220 Rheum officinale: 10.1016/S0944-7113(97)80075-X
182070 Saxifraga stolonifera: 10.5511/PLANTBIOTECHNOLOGY.16.129
880079 Rhododendron dauricum: 10.1007/S10600-010-9649-7
4329 Macadamia: 10.1021/JF061478A
3818 Arachis hypogaea: 10.1021/JF061478A
3625 Actinidia chinensis:
3435 Persea americana:
13450 Corylus: 10.1021/JF061478A
4640 Musa:
4615 Ananas comosus:
32201 Carya illinoinensis: 10.1021/JF061478A
55513 Pistacia vera: 10.1021/JF061478A
3755 Prunus dulcis: 10.1021/JF061478A
3645 Bertholletia excelsa: 10.1021/JF061478A
3337 Pinus: 10.1021/JF061478A
171929 Anacardium occidentale: 10.1021/JF061478A
51240 Juglans regia: 10.1021/JF061478A
40716 Paeonia obovata: 10.1248/CPB.48.201
29760 Vitis vinifera:
4442 Camellia sinensis:
3708 Brassica napus: 10.3389/FNUT.2022.822033
4530 Oryza sativa: 10.3390/MOLECULES16031917
119949 Myrtus communis: 10.1007/BF02467181
1407748 Camellia crassicolumna: 10.1021/JF802974M
2516462 Archidendron bubalinum: 10.1016/0031-9422(92)80375-O
666566 Rhodiola semenovii:
289766 Sclerocarya birrea: 10.1021/JF030374M
2726413 Sedum crassularia: 10.1016/0031-9422(93)85416-O
28519 Sedum sediforme: 10.1016/0031-9422(93)85416-O
508984 Schnella guianensis: 10.1016/0031-9422(88)80455-2
2291126 Fagopyrum acutatum: 10.1016/J.JEP.2005.02.029
516549 Fagopyrum dibotrys: 10.1016/J.JEP.2005.02.029
35925 Diospyros kaki:
171204 Acer barbinerve: 10.1007/S10600-011-0016-0
39993 Terminalia catappa: 10.1002/JCCS.199900085
296036 Phyllanthus emblica: 10.1021/NP000135I
296034 Phyllanthus niruri: 10.1016/0031-9422(92)80352-F
1387640 Mezoneuron benthamianum: 10.1076/1388-0209(200009)3841-AFT284
327901 Detarium microcarpum: 10.1016/0166-3542(93)90095-Z
1173659 Acacia omalophylla: 10.1016/S0031-9422(00)85959-2
1174874 Acacia pubifolia: 10.1016/S0031-9422(00)85959-2
139006 Acacia calamifolia: 10.1016/S0031-9422(00)85959-2
694541 Acacia doratoxylon: 10.1016/S0031-9422(00)85959-2
204988 Acacia adunca: 10.1016/S0031-9422(00)85959-2
1174755 Acacia clunies-rossiae: 10.1016/S0031-9422(00)85959-2
139013 Acacia oswaldii: 10.1016/S0031-9422(00)85959-2
138511 Acacia aulacocarpa: 10.1016/S0031-9422(00)85959-2
880440 Acacia pycnantha: 10.1016/S0031-9422(00)85959-2
1174758 Acacia complanata: 10.1016/S0031-9422(00)85959-2
1378425 Acacia trineura: 10.1016/S0031-9422(00)85959-2
224085 Acacia mangium: 10.1016/S0031-9422(00)85959-2
1174742 Acacia binervia: 10.1016/S0031-9422(00)85959-2
98504 Matricaria chamomilla: 10.1111/J.1365-2621.2005.TB08304.X
4400 Liquidambar styraciflua: 10.1016/0031-9422(93)85229-K
260143 Syzygium samarangense: 10.1248/CPB.40.2671
326968 Ziziphus jujuba: 10.1007/BF02291535
38942 Quercus robur: 10.1007/BF02249631
3760 Prunus persica:
1146880 Scurrula atropurpurea: 10.1248/CPB.51.343
41241 Rumex acetosa: 10.1016/J.FITOTE.2009.08.015
148713 Parapiptadenia rigida: 10.1021/NP100523S
29747 Mallotus japonicus: 10.1016/S0031-9422(00)98001-4
32239 Dasiphora fruticosa: 10.1007/BF00565058
208863 Myriophyllum aquaticum: 10.1021/NP50066A004
318062 Euphorbia hirta:
3888 Pisum sativum: 10.1021/JF000549H
36596 Prunus armeniaca: 10.1021/JF000549H
4236 Lactuca sativa: 10.1021/JF000549H
3758 Prunus domestica: 10.1021/JF000549H
42229 Prunus avium: 10.1021/JF000549H
3663 Cucurbita pepo: 10.1021/JF000549H
3494 Ficus carica: 10.1021/JF000549H
3750 Malus domestica: 10.1021/JF000549H
283210 Malus pumila: 10.1021/JF000549H
36609 Cydonia: 10.1021/JF000549H
4565 Triticum aestivum: 10.1021/JF000549H
3746 Fragaria: 10.1021/JF000549H
4039 Daucus carota: 10.1021/JF000549H
36616 Mespilus germanica: 10.1021/JF000549H
3827 Cicer arietinum: 10.1021/JF000549H
3885 Phaseolus vulgaris: 10.1021/JF000549H
21019 Castanea: 10.1021/JF000549H
3864 Lens culinaris: 10.1021/JF000549H
3906 Vicia faba: 10.1021/JF000549H
23211 Pyrus communis: 10.1021/JF000549H
175228 Ribes rubrum: 10.1021/JF000549H
23216 Rubus: 10.1021/JF000549H
301862 Annona reticulata: 10.1021/JF000549H
4072 Capsicum annuum: 10.1021/JF000549H
4111 Solanum melongena: 10.1021/JF000549H
22663 Punica granatum: 10.1021/JF000549H
4081 Solanum lycopersicum: 10.1021/JF000549H
229543 Hibiscus cannabinus: 10.1007/BF00574392
138017 Senegalia catechu: 10.1021/JF0531499
875646 Senegalia polyacantha: 10.1021/JF0531499
28974 Averrhoa carambola: 10.1007/S11418-008-0239-Y
29780 Mangifera indica: 10.1248/CPB.32.2676
122832 Platanus orientalis: 10.1023/B:CONC.0000025479.07578.5D
3617 Fagopyrum esculentum:
642531 Pyrola incarnata: 10.1016/0031-9422(89)80060-3
13442 Coffea: 10.1021/JF000026+
889930 Parkia biglobosa: 10.1016/S0367-326X(99)00137-9
46901 Persicaria hydropiper: 10.1016/S0031-9422(98)00426-9
255348 Rhus typhina: 10.1007/BF00633406
714442 Ampelopsis japonica: 10.1007/S11418-006-0119-2
91113 Orostachys fimbriata: 10.1016/J.FITOTE.2008.10.003
137220 Rheum officinale: 10.1016/S0944-7113(97)80075-X
182070 Saxifraga stolonifera: 10.5511/PLANTBIOTECHNOLOGY.16.129
9606 Homo sapiens: -
714442 Ampelopsis Japonica: -
137221 Rheum palmatum L.: -
137226 Rheum tanguticum Maxim. ex Balf.: -
137220 Rheum officinale Baill.: -
33090 Plants: -
714442 Ampelopsis Japonica: -
137221 Rheum palmatum L.: -
137226 Rheum tanguticum Maxim. ex Balf.: -
137220 Rheum officinale Baill.: -
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

Ziqiong Zhou, Yan Li, Fangyuan Wang, Guanghao Zhu, Shenglan Qi, Haonan Wang, Yuhe Ma, Rong Zhu, Yuejuan Zheng, Guangbo Ge, Ping Wang. Bioactive components and mechanisms of Pu-erh tea in improving levodopa metabolism in rats through COMT inhibition. Food & function. 2024 May; 15(10):5287-5299. doi: 10.1039/d4fo00538d. [PMID: 38639730]
Huimin Yong, Zeyu Wang, Jinbao Huang, Jun Liu. Preparation, characterization and application of antioxidant packaging films based on chitosan-epicatechin gallate conjugates with different substitution degrees. International journal of biological macromolecules. 2024 Mar; 260(Pt 2):129568. doi: 10.1016/j.ijbiomac.2024.129568. [PMID: 38246436]
Wei Zhu, Patricia I Oteiza. NADPH oxidase 1: A target in the capacity of dimeric ECG and EGCG procyanidins to inhibit colorectal cancer cell invasion. Redox biology. 2023 Jul; 65(?):102827. doi: 10.1016/j.redox.2023.102827. [PMID: 37516013]
Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
Maniraj Rathinam, Shaily Tyagi, Narasimham Dokka, Sathish Kumar Marimuthu, Hemant Kumar, Doddachowdappa Sagar, Prasanta K Dash, Ajit Kumar Shasany, Rohini Sreevathsa. The plant specialized metabolite epicatechin- 3-gallate (EC3G) perturbs lipid metabolism and attenuates fat accumulation in pigeonpea pod borer, Helicoverpa armigera. International journal of biological macromolecules. 2023 Mar; 231(?):123325. doi: 10.1016/j.ijbiomac.2023.123325. [PMID: 36681223]
Luyao Chen, Yaping Guo, Zixuan Wu, Shuwu Zhao, Zhaiyi Zhang, Fang Zheng, Likang Sun, Zheng Hao, Chen Xu, Tao Wang, Yanfei Peng. Epicatechin gallate prevents the de novo synthesis of fatty acid and the migration of prostate cancer cells. Acta biochimica et biophysica Sinica. 2021 Dec; 53(12):1662-1669. doi: 10.1093/abbs/gmab144. [PMID: 34718375]
Carmela Maria Montone, Sara Elsa Aita, Anna Arnoldi, Anna Laura Capriotti, Chiara Cavaliere, Andrea Cerrato, Carmen Lammi, Susy Piovesana, Giulia Ranaldi, Aldo Laganà. Characterization of the Trans-Epithelial Transport of Green Tea (C. sinensis) Catechin Extracts with In Vitro Inhibitory Effect against the SARS-CoV-2 Papain-like Protease Activity. Molecules (Basel, Switzerland). 2021 Nov; 26(21):. doi: 10.3390/molecules26216744. [PMID: 34771162]
Lijiao Kan, Edoardo Capuano, Vincenzo Fogliano, Ruud Verkerk, Jurriaan J Mes, Monic M M Tomassen, Teresa Oliviero. Inhibition of α-glucosidases by tea polyphenols in rat intestinal extract and Caco-2 cells grown on Transwell. Food chemistry. 2021 Nov; 361(?):130047. doi: 10.1016/j.foodchem.2021.130047. [PMID: 34029903]
Jia Lei, Yong Zhang, Xuechen Ni, Xuejing Yu, Xingguo Wang. Degradation of epigallocatechin and epicatechin gallates by a novel tannase TanHcw from Herbaspirillum camelliae. Microbial cell factories. 2021 Oct; 20(1):197. doi: 10.1186/s12934-021-01685-1. [PMID: 34641872]
Sunanta Wangkarn, Kate Grudpan, Chartchai Khanongnuch, Thanawat Pattananandecha, Sutasinee Apichai, Chalermpong Saenjum. Development of HPLC Method for Catechins and Related Compounds Determination and Standardization in Miang (Traditional Lanna Fermented Tea Leaf in Northern Thailand). Molecules (Basel, Switzerland). 2021 Oct; 26(19):. doi: 10.3390/molecules26196052. [PMID: 34641598]
Jinjin Yu, Weifeng Li, Xin Xiao, Qiuxia Huang, Jiabao Yu, Yajie Yang, Tengfei Han, Dezhu Zhang, Xiaofeng Niu. (-)-Epicatechin gallate blocks the development of atherosclerosis by regulating oxidative stress in vivo and in vitro. Food & function. 2021 Sep; 12(18):8715-8727. doi: 10.1039/d1fo00846c. [PMID: 34365492]
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