Artemetin (BioDeep_00000017256)

human metabolite PANOMIX_OTCML-2023 Endogenous

代谢物信息卡片

4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxy-

化学式: C20H20O8 (388.115812)
中文名称: 艾黄素, 艾黄素
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.37%

分子结构信息

SMILES: c1(c(c(c2c(c1)oc(c(c2=O)OC)c1ccc(c(c1)OC)OC)O)OC)OC
InChI: InChI=1S/C20H20O8/c1-23-11-7-6-10(8-12(11)24-2)18-20(27-5)17(22)15-13(28-18)9-14(25-3)19(26-4)16(15)21/h6-9,21H,1-5H3

描述信息

Artemetin is found in common verbena. Artemetin is a constituent of Artemisia species, Kuhnia eupatorioides (preferred genus name Brickellia), Achillea species, Brickellia species and others in the Compositae [CCD]
Constituent of Artemisia subspecies, Kuhnia eupatorioides (preferred genus name Brickellia), Achillea subspecies, Brickellia subspecies and others in the Compositae [CCD]. Artemetin is found in common verbena.
Artemetin is a member of flavonoids and an ether.
Artemetin is a natural product found in Achillea santolina, Psiadia viscosa, and other organisms with data available.
Artemitin is a flavonol found in Laggera pterodonta (DC.) Benth., with antioxidative, anti-inflammatory, and antiviral activity[1].
Artemitin is a flavonol found in Laggera pterodonta (DC.) Benth., with antioxidative, anti-inflammatory, and antiviral activity[1].

同义名列表

26 个代谢物同义名

4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxy-; 2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxy-4H-1-benzopyran-4-one; 2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxy-4H-chromen-4-one #; 2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxy-4H-chromen-4-one; 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxy-chromen-4-one; 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxychromen-4-one; Flavone, 5-hydroxy-3,3,4,6,7-pentamethoxy-; Quercetagetin 3,6,7,3,4-pentamethyl ether; Quercetagetin-3,6,7,3,4-pentamethylether; 5-hydroxy-3,3,4,6,7-pentamethoxy-flavone; 5-hydroxy-3,3,4,6,7-pentamethoxyflavone; 5-Hydroxy-3,3,4,6,7-pentamethoxyflavone; 5-Hydroxy-3,6,7,3,4-pentamethoxyflavone; 3,6,7,3,4-pentamethylquercetagetin; Penta-O-methylquercetagetin; RIGYMJVFEJNCKD-UHFFFAOYSA-N; UNII-73KMT7R64H; ARTEMISETIN(P); MEGxp0_002022; ACon1_000985; Artemisetin; 73KMT7R64H; Artemetin; Erianthin; Artemitin; Vx-6 cpd

数据库引用编号

14 个数据库交叉引用编号

ChEBI: CHEBI:175930
PubChem: 5320351
HMDB: HMDB0030095
ChEMBL: CHEMBL225700
LipidMAPS: LMPK12113017
MeSH: artemetin
ChemIDplus: 0000479903
MetaCyc: CPD-14860
KNApSAcK: C00004712
foodb: FDB001546
chemspider: 4478461
CAS: 479-90-3
medchemexpress: HY-N3017
PMhub: MS000203916

分类词条

代谢反应

4 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

polymethylated quercetin glucoside biosynthesis II - quercetagetin series (Chrysosplenium): 3,6,7-trimethylquercetagetin + SAM ⟶ 3,6,7,4'-tetramethylquercetagetin + H⁺ + SAH
superpathway of polymethylated quercetin/quercetagetin glucoside biosynthesis (Chrysosplenium): 3,6,7-trimethylquercetagetin + SAM ⟶ 3,6,7,4'-tetramethylquercetagetin + H⁺ + SAH

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

polymethylated quercetin glucoside biosynthesis II - quercetagetin series (Chrysosplenium): 3,6,7-trimethylquercetagetin + SAM ⟶ 3,6,7,4'-tetramethylquercetagetin + H⁺ + SAH
superpathway of polymethylated quercetin/quercetagetin glucoside biosynthesis (Chrysosplenium): 3,6,7-trimethylquercetagetin + SAM ⟶ 3,6,7,4'-tetramethylquercetagetin + H⁺ + SAH

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

141 个相关的物种来源信息

33090 马鞭草: -
13422 菊花: -
54477 Vitex agnus-castus:
413484 Vitex rotundifolia:
35608 Artemisia annua:
72344 Artemisia inculta:
119176 Pentanema britannicum:
119185 Pulicaria arabica: 10.1055/S-2007-971700
2813830 Callicarpa pilosissima:
1227617 Artemisia assoana: 10.1016/S0031-9422(00)83891-1
1227629 Artemisia lindleyana: 10.1021/NP50043A027
282752 Achillea nana: 10.1016/0305-1978(96)88878-8
282734 Achillea erba-rotta: 10.1016/0305-1978(96)88878-8
282753 Achillea nobilis: 10.1016/0305-1978(88)90033-6
282770 Achillea virescens:
72356 Artemisia verlotiorum:
262982 Artemisia apiacea:
496566 Artemisia carvifolia:
72332 Artemisia absinthium:
669133 Artemisia mongolica:
1903237 Artemisia vachanica:
205374 Artemisia rutifolia:
72351 Artemisia scoparia:
1458965 Chiliadenus montanus: 10.1016/0031-9422(89)80084-6
301866 Achillea tenuifolia:
1028379 Achillea santolina:
282769 Achillea teretifolia: 10.1016/S0031-9422(99)00054-0
72386 Artemisia arborescens:
282720 Achillea aspleniifolia:
13329 Achillea millefolium:
282730 Achillea collina:
282767 Achillea setacea: 10.1016/0305-1978(88)90071-3
359922 Achillea formosa: 10.1515/ZNC-1989-3-423
301871 Leucocyclus formosus: 10.1515/ZNC-1989-3-423
1550803 Brickellia baccharidea: 10.1016/S0031-9422(00)98581-9
482483 Achillea millefolium var. millefolium: 10.1016/0031-9422(90)85371-L
282726 Achillea clavennae:
282741 Achillea impatiens:
282718 Achillea alpina:
211591 Iphiona scabra: 10.1016/S0031-9422(00)81848-8
2029211 Achillea sibirica: 10.1016/S0305-1978(98)00112-4
595250 Cordia verbenacea:
246543 Cordia curassavica:
375289 Biebersteinia heterostemon: 10.1080/00387019909350045
79772 Verbena officinalis: 10.1007/S10600-011-9920-6
361442 Vitex negundo:
1908589 Tillandsia purpurea: 10.1021/NP50048A062
630296 Helichrysum chionosphaerum: 10.1016/0031-9422(80)85128-4
589716 Anthemis anthemiformis: 10.1016/0031-9422(94)00785-R
1548674 Streptoglossa odora: 10.1016/S0031-9422(00)80267-8
1548633 Pluchea odorata:
4002 Buxus sempervirens: 10.1021/NP50073A003
175517 Pluchea carolinensis: 10.1515/ZNC-1985-5-607
401901 Artemisia gorgonum: 10.1016/J.JEP.2011.09.039
2072400 Tanacetum sinaicum: 10.21608/BFSA.2001.65917
669119 Artemisia argentea:
1745167 Symphyopappus reticulatus: 10.1016/S0031-9422(00)98550-9
205378 Artemisia sieversiana: 10.1007/BF00579658
99024 Ajania fruticulosa: 10.1007/BF00565848
204215 Vitex trifolia: 10.1080/10286020310001625085
223869 Artemisia pedemontana: 10.1016/S0031-9422(00)81325-4
1287616 Artemisia nitida: 10.1016/S0031-9422(00)81325-4
1077900 Psiadia viscosa: 10.1016/S0031-9422(00)97976-7
1262115 Callicarpa longissima: 10.1021/NP200932K
441199 Laggera crispata: 10.1016/S0031-9422(96)00521-3
313968 Laggera pterodonta: 10.1016/S0031-9422(96)00521-3
309270 Ficus altissima: 10.1016/S0305-1978(99)00065-4
1550813 Brickellia cylindracea: 10.1016/0305-1978(83)90027-3
99040 Cladanthus arabicus: 10.1002/CHIN.199516211
54477 Vitex agnus-castus:
413484 Vitex rotundifolia:
35608 Artemisia annua:
72344 Artemisia inculta:
119176 Pentanema britannicum:
119185 Pulicaria arabica: 10.1055/S-2007-971700
2813830 Callicarpa pilosissima:
1227617 Artemisia assoana: 10.1016/S0031-9422(00)83891-1
1227629 Artemisia lindleyana: 10.1021/NP50043A027
282752 Achillea nana: 10.1016/0305-1978(96)88878-8
282734 Achillea erba-rotta: 10.1016/0305-1978(96)88878-8
282753 Achillea nobilis: 10.1016/0305-1978(88)90033-6
282770 Achillea virescens:
72356 Artemisia verlotiorum:
262982 Artemisia apiacea:
496566 Artemisia carvifolia:
72332 Artemisia absinthium:
669133 Artemisia mongolica:
1903237 Artemisia vachanica:
205374 Artemisia rutifolia:
72351 Artemisia scoparia:
1458965 Chiliadenus montanus: 10.1016/0031-9422(89)80084-6
301866 Achillea tenuifolia:
1028379 Achillea santolina:
282769 Achillea teretifolia: 10.1016/S0031-9422(99)00054-0
72386 Artemisia arborescens:
282720 Achillea aspleniifolia:
13329 Achillea millefolium:
282730 Achillea collina:
282767 Achillea setacea: 10.1016/0305-1978(88)90071-3
359922 Achillea formosa: 10.1515/ZNC-1989-3-423
301871 Leucocyclus formosus: 10.1515/ZNC-1989-3-423
1550803 Brickellia baccharidea: 10.1016/S0031-9422(00)98581-9
482483 Achillea millefolium var. millefolium: 10.1016/0031-9422(90)85371-L
282726 Achillea clavennae:
282741 Achillea impatiens:
282718 Achillea alpina:
211591 Iphiona scabra: 10.1016/S0031-9422(00)81848-8
2029211 Achillea sibirica: 10.1016/S0305-1978(98)00112-4
595250 Cordia verbenacea:
246543 Cordia curassavica:
375289 Biebersteinia heterostemon: 10.1080/00387019909350045
79772 Verbena officinalis: 10.1007/S10600-011-9920-6
361442 Vitex negundo:
1908589 Tillandsia purpurea: 10.1021/NP50048A062
630296 Helichrysum chionosphaerum: 10.1016/0031-9422(80)85128-4
589716 Anthemis anthemiformis: 10.1016/0031-9422(94)00785-R
1548674 Streptoglossa odora: 10.1016/S0031-9422(00)80267-8
1548633 Pluchea odorata:
4002 Buxus sempervirens: 10.1021/NP50073A003
175517 Pluchea carolinensis: 10.1515/ZNC-1985-5-607
401901 Artemisia gorgonum: 10.1016/J.JEP.2011.09.039
2072400 Tanacetum sinaicum: 10.21608/BFSA.2001.65917
669119 Artemisia argentea:
1745167 Symphyopappus reticulatus: 10.1016/S0031-9422(00)98550-9
205378 Artemisia sieversiana: 10.1007/BF00579658
99024 Ajania fruticulosa: 10.1007/BF00565848
204215 Vitex trifolia: 10.1080/10286020310001625085
223869 Artemisia pedemontana: 10.1016/S0031-9422(00)81325-4
1287616 Artemisia nitida: 10.1016/S0031-9422(00)81325-4
1077900 Psiadia viscosa: 10.1016/S0031-9422(00)97976-7
1262115 Callicarpa longissima: 10.1021/NP200932K
441199 Laggera crispata: 10.1016/S0031-9422(96)00521-3
313968 Laggera pterodonta: 10.1016/S0031-9422(96)00521-3
309270 Ficus altissima: 10.1016/S0305-1978(99)00065-4
1550813 Brickellia cylindracea: 10.1016/0305-1978(83)90027-3
99040 Cladanthus arabicus: 10.1002/CHIN.199516211
9606 Homo sapiens: -
35608 Artemisia Annua L.: -
79772 Verbena officinalis L.: -
114476 Gardenia jasminoides Ellis: -
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

Antonella Rosa, Raffaella Isola, Federica Pollastro, Mariella Nieddu. Effect of the natural polymethoxylated flavone artemetin on lipid oxidation and its impact on cancer cell viability and lipids. Fitoterapia. 2022 Jan; 156(?):105102. doi: 10.1016/j.fitote.2021.105102. [PMID: 34921927]
Akram Taleghani, Seyed Ahmad Emami, Zahra Tayarani-Najaran. Artemisia: a promising plant for the treatment of cancer. Bioorganic & medicinal chemistry. 2020 01; 28(1):115180. doi: 10.1016/j.bmc.2019.115180. [PMID: 31784199]
Jae-Yong Kim, Sang Hee Shim. Anti-Atherosclerotic Effects of Fruits of Vitex rotundifolia and Their Isolated Compounds via Inhibition of Human LDL and HDL Oxidation. Biomolecules. 2019 11; 9(11):. doi: 10.3390/biom9110727. [PMID: 31726713]
Xiaoli Han, Jinhua He, Qinyue Chen, Yali Sun, Xiulei Zhang, Zhengyi Gu, Xianyi Sha. Development of an LC-MS/MS-based assay to determine artemitin in rat plasma and its application in a pharmacokinetic study. Biomedical chromatography : BMC. 2018 Dec; 32(12):e4356. doi: 10.1002/bmc.4356. [PMID: 30073671]
Sergio Ortiz, Kamel Dali-Yahia, Pedro Vasquez-Ocmin, Raphaël Grougnet, Philippe Grellier, Sylvie Michel, Alexandre Maciuk, Sabrina Boutefnouchet. Heme-binding activity of methoxyflavones from Pentzia monodiana Maire (Asteraceae). Fitoterapia. 2017 Apr; 118(?):1-5. doi: 10.1016/j.fitote.2017.01.012. [PMID: 28167052]
Alice Martins, Rukmini Mignon, Marina Bastos, Daniela Batista, Nuno R Neng, José M F Nogueira, Catarina Vizetto-Duarte, Luísa Custódio, João Varela, Amélia P Rauter. In vitro antitumoral activity of compounds isolated from Artemisia gorgonum Webb. Phytotherapy research : PTR. 2014 Sep; 28(9):1329-34. doi: 10.1002/ptr.5133. [PMID: 24633846]
Pamela J Weathers, Melissa J Towler. The flavonoids casticin and artemetin are poorly extracted and are unstable in an Artemisia annua tea infusion. Planta medica. 2012 Jun; 78(10):1024-6. doi: 10.1055/s-0032-1314949. [PMID: 22673829]
Yuan-Wei Liu, Yuan-Bin Cheng, Chia-Ching Liaw, Chung-Hsiung Chen, Jih-Hwa Guh, Tsong-Long Hwang, Ji-Shu Tsai, Won-Bo Wang, Ya-Ching Shen. Bioactive diterpenes from Callicarpa longissima. Journal of natural products. 2012 Apr; 75(4):689-93. doi: 10.1021/np200932k. [PMID: 22429052]
V K Sridevi, Hemendra S Chouhan, Narendra K Singh, Sushil K Singh. Antioxidant and hepatoprotective effects of ethanol extract of Vitex glabrata on carbon tetrachloride-induced liver damage in rats. Natural product research. 2012; 26(12):1135-40. doi: 10.1080/14786419.2011.560849. [PMID: 22054305]
Ulrike Grienke, Judit Mihály-Bison, Daniela Schuster, Taras Afonyushkin, Markus Binder, Shu-hong Guan, Chun-ru Cheng, Gerhard Wolber, Hermann Stuppner, De-an Guo, Valery N Bochkov, Judith M Rollinger. Pharmacophore-based discovery of FXR-agonists. Part II: identification of bioactive triterpenes from Ganoderma lucidum. Bioorganic & medicinal chemistry. 2011 Nov; 19(22):6779-91. doi: 10.1016/j.bmc.2011.09.039. [PMID: 22014750]
Priscila de Souza, Arquimedes Gasparotto, Sandra Crestani, Maria Élida Alves Stefanello, Maria Consuelo Andrade Marques, José Eduardo da Silva-Santos, Cândida Aparecida Leite Kassuya. Hypotensive mechanism of the extracts and artemetin isolated from Achillea millefolium L. (Asteraceae) in rats. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2011 Jul; 18(10):819-25. doi: 10.1016/j.phymed.2011.02.005. [PMID: 21420289]
Philippe Rasoanaivo, Colin W Wright, Merlin L Willcox, Ben Gilbert. Whole plant extracts versus single compounds for the treatment of malaria: synergy and positive interactions. Malaria journal. 2011 Mar; 10 Suppl 1(?):S4. doi: 10.1186/1475-2875-10-s1-s4. [PMID: 21411015]
Renjun Guan, Daijie Wang, Zongyuan Yu, Xiao Wang, Tianfeng Lan. [Preparative isolation and purification of the active components from Viticis Fructus by high-speed counter-current chromatography]. Se pu = Chinese journal of chromatography. 2010 Nov; 28(11):1043-7. doi: . [PMID: 21381420]
Edinardo F F Matias, Karla K A Santos, José Galberto M Costa, Henrique D M Coutinho. Screening for in vitro phototoxic activity of methanol extracts of Croton campestris A., Ocimum gratissimum L. & Cordia verbenaceae DC. The Indian journal of medical research. 2010 Nov; 132(?):520-2. doi: 10.4103/0971-5916.73392. [PMID: 21150001]
Eliane M Z Michielin, Ana A Salvador, Carlos A S Riehl, Artur Smânia, Elza F A Smânia, Sandra R S Ferreira. Chemical composition and antibacterial activity of Cordia verbenacea extracts obtained by different methods. Bioresource technology. 2009 Dec; 100(24):6615-23. doi: 10.1016/j.biortech.2009.07.061. [PMID: 19683436]
Javid Hussain, Farman Ullah Khan, Najeeb Ur Rehman, Riaz Ullah, Zia Mohmmad, S Tasleem, A Naeem, M Raza Shah. One new triterpene ester from Nepeta suavis. Journal of Asian natural products research. 2009 Dec; 11(12):997-1000. doi: 10.1080/10286020903264085. [PMID: 20183267]
M Iqbal Choudhary, Saima Jalil, Sarfraz Ahmad Nawaz, Khalid Mohammed Khan, Rasool Bakhsh Tareen. Antiinflammatory and lipoxygenase inhibitory compounds from Vitex agnus-castus. Phytotherapy research : PTR. 2009 Sep; 23(9):1336-9. doi: 10.1002/ptr.2639. [PMID: 19173281]
Boglárka Csupor-Löffler, Zsuzsanna Hajdú, István Zupkó, Borbála Réthy, George Falkay, Peter Forgo, Judit Hohmann. Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines. Phytotherapy research : PTR. 2009 May; 23(5):672-6. doi: 10.1002/ptr.2697. [PMID: 19107850]
Shuyun Shi, Honghao Zhou, Yuping Zhang, Yu Zhao, Kelong Huang, Suqin Liu. A high-speed counter-current chromatography- HPLC-DAD method for preparative isolation and purification of two polymethoxylated flavones from Taraxacum mongolicum. Journal of chromatographic science. 2009 May; 47(5):349-53. doi: 10.1093/chromsci/47.5.349. [PMID: 19476701]
Jih-Jung Chen, Hung-Ming Wu, Chien-Fang Peng, Ih-Sheng Chen, Shih-Der Chu. seco-Abietane diterpenoids, a phenylethanoid derivative, and antitubercular constituents from Callicarpa pilosissima. Journal of natural products. 2009 Feb; 72(2):223-8. doi: 10.1021/np800721f. [PMID: 19193025]
Manuela Saddi, Adriana Sanna, Filippo Cottiglia, Lorenza Chisu, Laura Casu, Leonardo Bonsignore, Alessandro De Logu. Antiherpevirus activity of Artemisia arborescens essential oil and inhibition of lateral diffusion in Vero cells. Annals of clinical microbiology and antimicrobials. 2007 Sep; 6(?):10. doi: 10.1186/1476-0711-6-10. [PMID: 17894898]
Shiming Li, Min-Hsiung Pan, Ching-Shu Lai, Chih-Yu Lo, Slavik Dushenkov, Chi-Tang Ho. Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines. Bioorganic & medicinal chemistry. 2007 May; 15(10):3381-9. doi: 10.1016/j.bmc.2007.03.021. [PMID: 17391969]
B Sathiamoorthy, Prasoon Gupta, Manmeet Kumar, Ashok K Chaturvedi, P K Shukla, Rakesh Maurya. New antifungal flavonoid glycoside from Vitex negundo. Bioorganic & medicinal chemistry letters. 2007 Jan; 17(1):239-42. doi: 10.1016/j.bmcl.2006.09.051. [PMID: 17027268]
Wei-Xia Song, Teng-Fei Ji, Yi-Kang Si, Ya-Lun Su. [Studies on chemical constituents in herb from Artemisia rupestris]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Nov; 31(21):1790-2. doi: . [PMID: 17260794]
Cheryl Lans, Nancy Turner, Gerhard Brauer, Grant Lourenco, Karla Georges. Ethnoveterinary medicines used for horses in Trinidad and in British Columbia, Canada. Journal of ethnobiology and ethnomedicine. 2006 Aug; 2(?):31. doi: 10.1186/1746-4269-2-31. [PMID: 16893454]
Takeo Yoshioka, Tomohisa Inokuchi, Shozo Fujioka, Yasuo Kimura. Phenolic compounds and flavonoids as plant growth regulators from fruit and leaf of Vitex rotundifolia. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2004 Jul; 59(7-8):509-14. doi: 10.1515/znc-2004-7-810. [PMID: 15813370]
M C Bayeux, A T Fernandes, M A Foglio, J E Carvalho. Evaluation of the antiedematogenic activity of artemetin isolated from Cordia curassavica DC. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2002 Oct; 35(10):1229-32. doi: 10.1590/s0100-879x2002001000017. [PMID: 12424497]
I Sánchez, J Calderón, B Ruiz, J Tellez, L Calzada, J Taboada. In vitro cytotoxicity of flavonoids against MK2 and C6 tumour cells. Phytotherapy research : PTR. 2001 Jun; 15(4):290-3. doi: 10.1002/ptr.954. [PMID: 11406849]
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