Chrysosplenetin (BioDeep_00000000224)

Secondary id: BioDeep_00000270025, BioDeep_00000869351, BioDeep_00001867476

human metabolite PANOMIX_OTCML-2023 blood metabolite

代谢物信息卡片

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

化学式: C19H18O8 (374.1001628)
中文名称: 猫眼草黄素, 金腰乙素, 金腰乙素
谱图信息: 最多检出来源 Homo sapiens(blood) 0.29%

分子结构信息

SMILES: c1(c(c(c2c(c1)oc(c(c2=O)OC)c1ccc(c(c1)OC)O)O)OC)OC
InChI: InChI=1S/C19H18O8/c1-23-11-7-9(5-6-10(11)20)17-19(26-4)16(22)14-12(27-17)8-13(24-2)18(25-3)15(14)21/h5-8,20-21H,1-4H3

描述信息

Chrysosplenetin, also known as quercetagetin 3,6,7,3-tetramethyl ether or 3,6,7,3-tetra-methylquercetagetin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, chrysosplenetin is considered to be a flavonoid lipid molecule. Chrysosplenetin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Chrysosplenetin can be found in german camomile, which makes chrysosplenetin a potential biomarker for the consumption of this food product. Chrysosplenetin is an O-methylated flavonol. It can be found in the root of Berneuxia thibetica and in Chamomilla recutita .
Chrysosplenetin is a tetramethoxyflavone that is the 3,6,7,3-tetramethyl ether derivative of quercetagetin. It has a role as an antiviral agent and a plant metabolite. It is a tetramethoxyflavone and a dihydroxyflavone. It is functionally related to a quercetagetin.
Chrysosplenetin is a natural product found in Haplophyllum myrtifolium, Cleome amblyocarpa, and other organisms with data available.
Chrysosplenetin is one of the polymethoxylated flavonoids in Artemisia annua L. (Compositae) and other several Chinese herbs. Chrysosplenetin inhibits P-gp activity and reverses the up-regulated P-gp and MDR1 levels induced by artemisinin (ART). Chrysosplenetin significantly augments the rat plasma level and anti-malarial efficacy of ART, partially due to the uncompetitive inhibition effect of Chrysosplenetin on rat CYP3A[1].
Chrysosplenetin is one of the polymethoxylated flavonoids in Artemisia annua L. (Compositae) and other several Chinese herbs. Chrysosplenetin inhibits P-gp activity and reverses the up-regulated P-gp and MDR1 levels induced by artemisinin (ART). Chrysosplenetin significantly augments the rat plasma level and anti-malarial efficacy of ART, partially due to the uncompetitive inhibition effect of Chrysosplenetin on rat CYP3A[1].

同义名列表

18 个代谢物同义名

4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,7-trimethoxy-; 4H-1-Benzopyran-4-one,5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,7-trimethoxy-; 4H-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,7-trimethoxy-; 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,7-trimethoxy-4H-1-benzopyran-4-one; 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,7-trimethoxy-4H-chromen-4-one; 5-Hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3,6,7-trimethoxy-chromen-4-one; 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,7-trimethoxychromen-4-one; 5,4-Dihydroxy-3,6,7,3-tetramethoxyflavone; Quercetagetin 3,6,7,3-tetramethyl ether; 3,6,7,3-tetra-methylquercetagetin; 3,6,7,3-tetramethylquercetagetin; Chrysosplenetin B; Chrysosptertin B; Chrysosplenetin; UNII-9AA5Z8PMYE; CHRYSOSPLENOL B; Polycladin; 9AA5Z8PMYE

数据库引用编号

21 个数据库交叉引用编号

ChEBI: CHEBI:3689
KEGG: C10030
PubChem: 5281608
HMDB: HMDB0250217
Metlin: METLIN51421
ChEMBL: CHEMBL33256
Wikipedia: Chrysosplenetin
LipidMAPS: LMPK12113009
ChemIDplus: 0000603565
MetaCyc: CPD-10529
KNApSAcK: C00004704
foodb: FDB005989
chemspider: 4444927
CAS: 69234-29-3
CAS: 603-56-5
medchemexpress: HY-N1457
PMhub: MS000021230
PubChem: 12216
3DMET: B03473
NIKKAJI: J326.151D
RefMet: Chrysosplenetin

分类词条

代谢反应

2 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(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

79 个相关的物种来源信息

33090 五台金腰: -
441199 Laggera crispata:
54477 Vitex agnus-castus: 10.1016/S0031-9422(97)00127-1
72345 Artemisia lucentica: 10.1016/0031-9422(88)80018-9
72350 Artemisia reptans: 10.1016/0031-9422(88)80018-9
72329 Artemisia herba-alba: 10.1016/0031-9422(88)80018-9
98504 Matricaria chamomilla: 10.1016/S0305-1978(98)00124-0
119176 Pentanema britannicum: 10.1016/0031-9422(91)83681-A
282752 Achillea nana: 10.1016/0305-1978(96)88878-8
282734 Achillea erba-rotta: 10.1016/0305-1978(96)88878-8
282727 Achillea clusiana: 10.1016/0305-1978(96)88878-8
927720 Artemisia copa: 10.1055/S-2007-969139
35608 Artemisia annua:
65409 Scutellaria baicalensis: 10.1111/J.1600-0609.2009.01365.X
205374 Artemisia rutifolia:
669133 Artemisia mongolica:
262982 Artemisia apiacea:
496566 Artemisia carvifolia:
205378 Artemisia sieversiana:
1458965 Chiliadenus montanus: 10.1016/0031-9422(89)80084-6
259893 Artemisia argyi: 10.1021/ACS.JNATPROD.2C00146
1249038 Miliusa balansae: 10.1002/CHIN.200550192
1721085 Pentzia eenii: 10.1016/0031-9422(90)89035-8
1391947 Stachys aegyptiaca: 10.1016/S0031-9422(00)95197-5
313968 Laggera pterodonta: 10.1016/S0031-9422(96)00521-3
61245 Chrysosplenium grayanum: 10.1021/NP50075A029
310241 Stylidocleome brachycarpa:
1522775 Thulinella chrysantha:
1077932 Cleome amblyocarpa:
282717 Achillea ageratum: 10.1016/S0031-9422(96)00774-1
1114741 Grindelia hirsutula: 10.1515/ZNC-1994-5-618
662482 Grindelia camporum: 10.1515/ZNC-1994-5-618
1114766 Grindelia tarapacana:
1898706 Getonia floribunda: 10.1021/JM00036A012
72338 Artemisia cana: 10.1016/S0031-9422(00)85924-5
1006077 Haplophyllum myrtifolium: 10.1016/S0367-326X(03)00147-3
2872361 Lantana achyranthifolia: 10.1055/S-2007-969816
80774 Chrysosplenium alternifolium: 10.1007/S10600-009-9422-Y
1911725 Leucheria runcinata: 10.1016/S0031-9422(00)89799-X
441199 Laggera crispata:
54477 Vitex agnus-castus: 10.1016/S0031-9422(97)00127-1
72345 Artemisia lucentica: 10.1016/0031-9422(88)80018-9
72350 Artemisia reptans: 10.1016/0031-9422(88)80018-9
72329 Artemisia herba-alba: 10.1016/0031-9422(88)80018-9
98504 Matricaria chamomilla: 10.1016/S0305-1978(98)00124-0
119176 Pentanema britannicum: 10.1016/0031-9422(91)83681-A
282752 Achillea nana: 10.1016/0305-1978(96)88878-8
282734 Achillea erba-rotta: 10.1016/0305-1978(96)88878-8
282727 Achillea clusiana: 10.1016/0305-1978(96)88878-8
927720 Artemisia copa: 10.1055/S-2007-969139
35608 Artemisia annua:
65409 Scutellaria baicalensis: 10.1111/J.1600-0609.2009.01365.X
205374 Artemisia rutifolia:
669133 Artemisia mongolica:
262982 Artemisia apiacea:
496566 Artemisia carvifolia:
205378 Artemisia sieversiana:
1458965 Chiliadenus montanus: 10.1016/0031-9422(89)80084-6
259893 Artemisia argyi: 10.1021/ACS.JNATPROD.2C00146
1249038 Miliusa balansae: 10.1002/CHIN.200550192
1721085 Pentzia eenii: 10.1016/0031-9422(90)89035-8
1391947 Stachys aegyptiaca: 10.1016/S0031-9422(00)95197-5
313968 Laggera pterodonta: 10.1016/S0031-9422(96)00521-3
61245 Chrysosplenium grayanum: 10.1021/NP50075A029
310241 Stylidocleome brachycarpa:
1522775 Thulinella chrysantha:
1077932 Cleome amblyocarpa:
282717 Achillea ageratum: 10.1016/S0031-9422(96)00774-1
1114741 Grindelia hirsutula: 10.1515/ZNC-1994-5-618
662482 Grindelia camporum: 10.1515/ZNC-1994-5-618
1114766 Grindelia tarapacana:
1898706 Getonia floribunda: 10.1021/JM00036A012
72338 Artemisia cana: 10.1016/S0031-9422(00)85924-5
1006077 Haplophyllum myrtifolium: 10.1016/S0367-326X(03)00147-3
2872361 Lantana achyranthifolia: 10.1055/S-2007-969816
80774 Chrysosplenium alternifolium: 10.1007/S10600-009-9422-Y
1911725 Leucheria runcinata: 10.1016/S0031-9422(00)89799-X
9606 Homo sapiens: -
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

Tanja Hell, Adriano Rutz, Lara Dürr, Maciej Dobrzyński, Jakob K Reinhardt, Timo Lehner, Morris Keller, Anika John, Mahabir Gupta, Olivier Pertz, Matthias Hamburger, Jean-Luc Wolfender, Eliane Garo. Combining Activity Profiling with Advanced Annotation to Accelerate the Discovery of Natural Products Targeting Oncogenic Signaling in Melanoma. Journal of natural products. 2022 06; 85(6):1540-1554. doi: 10.1021/acs.jnatprod.2c00146. [PMID: 35640148]
Yulin Ren, Esperanza J Carcache de Blanco, James R Fuchs, Djaja D Soejarto, Joanna E Burdette, Steven M Swanson, A Douglas Kinghorn. Potential Anticancer Agents Characterized from Selected Tropical Plants. Journal of natural products. 2019 03; 82(3):657-679. doi: 10.1021/acs.jnatprod.9b00018. [PMID: 30830783]
Yannan Li, Jing Ning, Yan Wang, Chao Wang, Chengpeng Sun, Xiaokui Huo, Zhenlong Yu, Lei Feng, Baojing Zhang, Xiangge Tian, Xiaochi Ma. Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicology letters. 2018 Sep; 294(?):27-36. doi: 10.1016/j.toxlet.2018.05.008. [PMID: 29753067]
Thanika Promchai, Atchara Jaidee, Sarot Cheenpracha, Kongkiat Trisuwan, Roonglawan Rattanajak, Sumalee Kamchonwongpaisan, Surat Laphookhieo, Stephen G Pyne, Thunwadee Ritthiwigrom. Antimalarial Oxoprotoberberine Alkaloids from the Leaves of Miliusa cuneata. Journal of natural products. 2016 Apr; 79(4):978-83. doi: 10.1021/acs.jnatprod.5b01054. [PMID: 26928423]
Qin-Chang Zhu, Yi Wang, Ya-Ping Liu, Rui-Qi Zhang, Xiang Li, Wen-Han Su, Fei Long, Xiao-Dong Luo, Tao Peng. Inhibition of enterovirus 71 replication by chrysosplenetin and penduletin. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2011 Oct; 44(3):392-8. doi: 10.1016/j.ejps.2011.08.030. [PMID: 21914477]
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]
Bailian Liu, Ting Zhang, Xiaoqi Zhang, Wencai Ye, Yaolan Li. [Chemical constituents of Laggera pterodonta]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Mar; 35(5):602-6. doi: 10.4268/cjcmm20100513. [PMID: 20506820]
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]
Guang-Zhong Yang, Yun-Fang Li, Xin Yu, Zhi-Nan Mei. Terpenoids and flavonoids from Laggera pterodonta. Yao xue xue bao = Acta pharmaceutica Sinica. 2007 May; 42(5):511-5. doi: . [PMID: 17703774]
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]
M E Wall, M C Wani, F Fullas, J B Oswald, D M Brown, T Santisuk, V Reutrakul, A T McPhail, N R Farnsworth, J M Pezzuto. Plant antitumor agents. 31. The calycopterones, a new class of biflavonoids with novel cytotoxicity in a diverse panel of human tumor cell lines. Journal of medicinal chemistry. 1994 May; 37(10):1465-70. doi: 10.1021/jm00036a012. [PMID: 8182705]