3-MGA (BioDeep_00000230531)

 

Secondary id: BioDeep_00000035455, BioDeep_00000621473, BioDeep_00001878703

PANOMIX_OTCML-2023


代谢物信息卡片


(2~{S},3~{S},4~{S},5~{R},6~{R})-6-[[(3~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{a}~{S},11~{S},12~{a}~{R},14~{a}~{R},14~{b}~{S})-11-carboxy-4,4,6~{a},6~{b},8~{a},11,14~{b}-heptamethyl-14-oxidanylidene-2,3,4~{a},5,6,7,8,9,10,12,12~{a},14~{a}-dodecahydro-1~{H}-picen-3-yl]oxy]-3,4,5-tris(oxidanyl)oxane-2-carboxylic acid

化学式: C36H54O10 (646.3716784)
中文名称: 甘草次酸单葡萄糖醛酸苷, 单葡萄糖醛酸甘草次酸, 甘草次酸 3-O-单-beta-D-葡糖苷酸
谱图信息: 最多检出来源 Bos taurus(endogenous) 94.12%

分子结构信息

SMILES: CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)C(=O)O)O)O)O)C)C(=O)C=C5C3(CCC6(C5CC(CC6)(C)C(=O)O)C)C)C)C
InChI: InChI=1S/C36H54O10/c1-31(2)21-8-11-36(7)27(34(21,5)10-9-22(31)45-29-25(40)23(38)24(39)26(46-29)28(41)42)20(37)16-18-19-17-33(4,30(43)44)13-12-32(19,3)14-15-35(18,36)6/h16,19,21-27,29,38-40H,8-15,17H2,1-7H3,(H,41,42)(H,43,44)/t19-,21-,22-,23-,24-,25+,26-,27+,29+,32+,33-,34-,35+,36+/m0/s1

描述信息

Glycyrrhetic acid 3-O-glucuronide is a triterpenoid saponin that is the 3-O-beta-glucuronide of glycyrrhetic acid. It is a metabolite of glycyrrhizin contained in licorice and potentially a causative agent in the pathogenesis of pseudoaldosteronism. It has a role as an anti-allergic agent, a sweetening agent, an EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor, a human xenobiotic metabolite and a plant metabolite. It is a monosaccharide derivative, a beta-D-glucosiduronic acid, a triterpenoid saponin, a pentacyclic triterpenoid, an oxo dicarboxylic acid and an enone. It is functionally related to a glycyrrhetinic acid.
A triterpenoid saponin that is the 3-O-beta-glucuronide of glycyrrhetic acid. It is a metabolite of glycyrrhizin contained in licorice and potentially a causative agent in the pathogenesis of pseudoaldosteronism.
Glycyrrhetic acid 3-O-β-D-glucuronide, isolated from glycyrrhiza, is an important derivative of glycyrrhizin (GL) with an anti -allergic activity[1]. Glycyrrhetic acid 3-O-β-D-glucuronide (GAMG) shows that β‐glucuronidases (β‐GUS) are key GAMG-producing enzymes, displaying a high potential to convert GL directly into GAMG[2].Glycyrrhetic acid 3-O-β-D-glucuronide is valuable as a sweetener.
Glycyrrhetic acid 3-O-β-D-glucuronide, isolated from glycyrrhiza, is an important derivative of glycyrrhizin (GL) with an anti -allergic activity[1]. Glycyrrhetic acid 3-O-β-D-glucuronide (GAMG) shows that β‐glucuronidases (β‐GUS) are key GAMG-producing enzymes, displaying a high potential to convert GL directly into GAMG[2].Glycyrrhetic acid 3-O-β-D-glucuronide is valuable as a sweetener.

同义名列表

36 个代谢物同义名

(2~{S},3~{S},4~{S},5~{R},6~{R})-6-[[(3~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{a}~{S},11~{S},12~{a}~{R},14~{a}~{R},14~{b}~{S})-11-carboxy-4,4,6~{a},6~{b},8~{a},11,14~{b}-heptamethyl-14-oxidanylidene-2,3,4~{a},5,6,7,8,9,10,12,12~{a},14~{a}-dodecahydro-1~{H}-picen-3-yl]oxy]-3,4,5-tris(oxidanyl)oxane-2-carboxylic acid; (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid; (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; beta-D-Glucopyranosiduronic acid, (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl; (3beta,20beta)-20-carboxy-11-oxo-30-norolean-12-en-3-yl beta-D-glucopyranosiduronic acid; 30-hydroxy-11,30-dioxoolean-12-en-3beta-yl beta-D-glucopyranosiduronic acid; 29-Hydroxy-11,29-dioxoolean-12-en-3-yl hexopyranosiduronic acid; 3-O-beta-D-glucuronopyranosyl-18beta-glycyrrhetinic acid; 3beta-D-(monoglucuronyl)-18beta-glycyrrhetinic acid; 18beta-glycyrrhetinic acid-3-o-beta-d-glucuronide; 1-(18 beta-glycyrrhet-3-yl)glucopyranuronic acid; 1-(18beta-Glycyrrhet-3-yl)glucopyranuronic acid; glycyrrhetinic acid 3-O-mono-beta-D-glucuronide; glycyrrhetinic acid acid 3-O-beta-D-glucuronide; Glycyrrhetic acid 3-O-mono-beta-D-glucuronide; glycyrrhetic acid 3-O-beta-D-monoglucuronide; 3-(monoglucuron-1-yl)-18-glycyrrhetic acid; 3-O-Glucuronopyranosylglycyrrhetinic acid; Glycyrrhetic acid 3-O-beta-D-glucuronide; glycyrrhetinic acid 3-O-monoglucuronide; Glycyrrhetic Acid 3-O-|A-D-Glucuronide; Glycyrrhetic acid 3-O-β-D-glucuronide; 3-monoglucuronyl glycyrrhetinic acid; 3-monoglucuronyl-glycyrrhetinic acid; Glycyrrhetic acid 3-O--D-glucuronide; Glycyrrhetinic acid Monoglucuronide; 18beta-glycyrrhetyl-3-O-glucuronide; glycyrrhetinic acid 3-O-glucuronide; glycyrrhetic acid-3-O-glucuronide; Glycyrrhetic Acid 3-O-Glucuronide; GLYCYRRHETICACID3-O-GLUCURONIDE; glycyrrhetyl 3-monoglucuronide; Starrhizin; 3-MGA; FJL; Glycyrrhetic acid 3-O-mono-β-D-glucuronide



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

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)

1 个相关的物种来源信息

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

  • Osamu Morinaga, Kan'ichiro Ishiuchi, Takeshi Ohkita, Chuanting Tian, Asuka Hirasawa, Miaki Mitamura, Yasuhito Maki, Tomoya Yasujima, Hiroaki Yuasa, Toshiaki Makino. Isolation of a novel glycyrrhizin metabolite as a causal candidate compound for pseudoaldosteronism. Scientific reports. 2018 10; 8(1):15568. doi: 10.1038/s41598-018-33834-9. [PMID: 30348944]
  • Rui Fan, Nan Li, Honggao Xu, Jun Xiang, Lei Wang, Yanxiang Gao. The mechanism of hydrothermal hydrolysis for glycyrrhizic acid into glycyrrhetinic acid and glycyrrhetinic acid 3-O-mono-β-D-glucuronide in subcritical water. Food chemistry. 2016 Jan; 190(?):912-921. doi: 10.1016/j.foodchem.2015.06.039. [PMID: 26213056]
  • Myrna Adianti, Chie Aoki, Mari Komoto, Lin Deng, Ikuo Shoji, Tutik Sri Wahyuni, Maria Inge Lusida, Soetjipto, Hiroyuki Fuchino, Nobuo Kawahara, Hak Hotta. Anti-hepatitis C virus compounds obtained from Glycyrrhiza uralensis and other Glycyrrhiza species. Microbiology and immunology. 2014 Mar; 58(3):180-7. doi: 10.1111/1348-0421.12127. [PMID: 24397541]
  • Toshiaki Makino. 3-Monoglucuronyl glycyrrhretinic acid is a possible marker compound related to licorice-induced pseudoaldosteronism. Biological & pharmaceutical bulletin. 2014; 37(6):898-902. doi: 10.1248/bpb.b13-00997. [PMID: 24882402]
  • R Xu, Q Xiao, Y Cao, J Yang. Comparison of the exposure of glycyrrhizin and its metabolites and the pseudoaldosteronism after intravenous administration of alpha- and beta-glycyrrhizin in rat. Drug research. 2013 Dec; 63(12):620-4. doi: 10.1055/s-0033-1349837. [PMID: 23864391]
  • Toshiaki Makino, Kyoko Okajima, Rie Uebayashi, Nobuhiro Ohtake, Katsuhisa Inoue, Hajime Mizukami. 3-Monoglucuronyl-glycyrrhretinic acid is a substrate of organic anion transporters expressed in tubular epithelial cells and plays important roles in licorice-induced pseudoaldosteronism by inhibiting 11β-hydroxysteroid dehydrogenase 2. The Journal of pharmacology and experimental therapeutics. 2012 Aug; 342(2):297-304. doi: 10.1124/jpet.111.190009. [PMID: 22543032]
  • Nobuhiro Ohtake, Akiko Kido, Kunitsugu Kubota, Naoko Tsuchiya, Toshimi Morita, Yoshio Kase, Shuichi Takeda. A possible involvement of 3-monoglucuronyl-glycyrrhetinic acid, a metabolite of glycyrrhizin (GL), in GL-induced pseudoaldosteronism. Life sciences. 2007 Apr; 80(17):1545-52. doi: 10.1016/j.lfs.2007.01.033. [PMID: 17331546]
  • T Akao. Differences in the metabolism of glycyrrhizin, glycyrrhetic acid and glycyrrhetic acid monoglucuronide by human intestinal flora. Biological & pharmaceutical bulletin. 2000 Dec; 23(12):1418-23. doi: 10.1248/bpb.23.1418. [PMID: 11145169]
  • H Kato, M Kanaoka, S Yano, M Kobayashi. 3-Monoglucuronyl-glycyrrhetinic acid is a major metabolite that causes licorice-induced pseudoaldosteronism. The Journal of clinical endocrinology and metabolism. 1995 Jun; 80(6):1929-33. doi: 10.1210/jcem.80.6.7775643. [PMID: 7775643]
  • Y Yamamura, J Kawakami, T Santa, H Kotaki, K Uchino, Y Sawada, T Iga. Selective high-performance liquid chromatographic method for the determination of glycyrrhizin and glycyrrhetic acid-3-O-glucuronide in biological fluids: application of ion-pair extraction and fluorescence labelling agent. Journal of chromatography. 1991 Jun; 567(1):151-60. doi: 10.1016/0378-4347(91)80319-8. [PMID: 1918242]
  • M Kanaoka, H Kato, S Yano. Studies on the enzyme immunoassay of bio-active constituents contained in oriental medicinal drugs. V. Preparation of bovine serum albumin conjugate and beta-galactosidase labelled antigen for enzyme immunoassay of 3 beta-(monoglucuron-1' beta-yl)-18 beta-glycyrrhetic acid. Chemical & pharmaceutical bulletin. 1990 Jan; 38(1):221-4. doi: 10.1248/cpb.38.221. [PMID: 2110868]
  • M Kanaoka, S Yano, H Kato, T Nakada. Synthesis and separation of 18 beta-glycyrrhetyl monoglucuronide from serum of a patient with glycyrrhizin-induced pseudo-aldosteronism. Chemical & pharmaceutical bulletin. 1986 Dec; 34(12):4978-83. doi: NULL. [PMID: 3568205]