Glycolithocholate sulphate (BioDeep_00000019574)

 

Secondary id: BioDeep_00000008589

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Bile acids


代谢物信息卡片


2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

化学式: C26H43NO7S (513.276)
中文名称: 磺基甘氨石胆酸, 硫酸甘糖胆酸
谱图信息: 最多检出来源 Homo sapiens(plant) 14.86%

Reviewed

Last reviewed on 2024-07-19.

Cite this Page

Glycolithocholate sulphate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/glycolithocholate_sulphate (retrieved 2025-02-17) (BioDeep RN: BioDeep_00000019574). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(CCC(=O)NCC(=O)O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)OS(=O)(=O)O)C)C
InChI: InChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

描述信息

Sulfolithocholylglycine is an acyl glycine and a bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID:16949895). Sulfolithocholylglycine is a sulfated bile acids which has a greater renal clearance rate than lithocholylglycine. [HMDB]
Sulfolithocholylglycine is an acyl glycine and a bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct, therefore, exist in a glycine conjugated form (PMID: 16949895). Sulfolithocholylglycine is a sulfated bile acid which has a greater renal clearance rate than lithocholylglycine.
D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts
D005765 - Gastrointestinal Agents > D002793 - Cholic Acids
Glycolithocholic acid 3-sulfate (SLCG) is a cholic acid derivative and a metabolite of glycolithocholic acid. Glycolithocholic acid 3-sulfate inhibits replication of HIV-1 in vitro. Glycolithocholic acid 3-sulfate can be used for the research of HIV infection and gallbladder disease[1][2].

同义名列表

33 个代谢物同义名

2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid; [(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid; N-[(3alpha,5beta)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycine; N-[(3α,5β)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycine; 3alpha-Hydroxy-5beta-cholanoylglycine 3-sulphate; 3alpha-Hydroxy-5beta-cholanoylglycine 3-sulfate; 3α-Hydroxy-5β-cholanoylglycine 3-sulphate; 3α-Hydroxy-5β-cholanoylglycine 3-sulfate; Glycolithocholic acid 3-sulphuric acid; Glycolithocholic acid 3-sulfuric acid; Glycolithocholic acid 3alpha-sulphate; Glycolithocholic acid sulphuric acid; Glycolithocholic acid 3alpha-sulfate; Glycolithocholic acid sulfuric acid; Glycolithocholic acid 3α-sulphate; Glycolithocholic acid 3-sulphate; Glycolithocholic acid 3α-sulfate; Glycolithocholic acid 3-sulfate; Glycolithocholic acid sulphate; Glycolithocholic acid sulfate; Glycolithocholate 3-sulphate; Sulphoglycolithocholic acid; Glycolithocholate 3-sulfate; Sulfoglycolithocholic acid; Glycolithocholate sulphate; Glycolithocholate sulfate; Sulpholithocholylglycine; Sulfolithocholylglycine; Sulphoglycolithocholate; Sulfolithoglycocholine; Sulfoglycolithocholate; SLCG; Sulfoglycolithocholate



数据库引用编号

17 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)

3 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。

亚细胞结构定位 关联基因列表


文献列表

  • Issey Takehara, Nobuaki Watanabe, Daiki Mori, Osamu Ando, Hiroyuki Kusuhara. Effect of Rifampicin on the Plasma Concentrations of Bile Acid-O-Sulfates in Monkeys and Human Liver-Transplanted Chimeric Mice With or Without Bile Flow Diversion. Journal of pharmaceutical sciences. 2019 08; 108(8):2756-2764. doi: 10.1016/j.xphs.2019.03.021. [PMID: 30905707]
  • Veronika Thöni, Alexandra Pfister, Andreas Melmer, Barbara Enrich, Karin Salzmann, Susanne Kaser, Claudia Lamina, Christoph F Ebenbichler, Hubert Hackl, Herbert Tilg, Alexander R Moschen. Dynamics of Bile Acid Profiles, GLP-1, and FGF19 After Laparoscopic Gastric Banding. The Journal of clinical endocrinology and metabolism. 2017 08; 102(8):2974-2984. doi: 10.1210/jc.2017-00235. [PMID: 28591793]
  • Noam Zelcer, Glen Reid, Peter Wielinga, Annemieke Kuil, Ingrid van der Heijden, John D Schuetz, Piet Borst. Steroid and bile acid conjugates are substrates of human multidrug-resistance protein (MRP) 4 (ATP-binding cassette C4). The Biochemical journal. 2003 Apr; 371(Pt 2):361-7. doi: 10.1042/bj20021886. [PMID: 12523936]
  • Zhe-Sheng Chen, Elizabeth Hopper-Borge, Martin G Belinsky, Irina Shchaveleva, Elena Kotova, Gary D Kruh. Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10). Molecular pharmacology. 2003 Feb; 63(2):351-8. doi: 10.1124/mol.63.2.351. [PMID: 12527806]
  • Norihiro Kobayashi, Hiroshi Katsumata, Yoshiaki Uto, Junichi Goto, Toshifumi Niwa, Koju Kobayashi, Yoshiaki Mizuuchi. A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test. Steroids. 2002 Sep; 67(10):827-33. doi: 10.1016/s0039-128x(02)00036-3. [PMID: 12231118]
  • H A Lemonde, A W Johnson, P T Clayton. The identification of unusual bile acid metabolites by tandem mass spectrometry: use of low-energy collision-induced dissociation to produce informative spectra. Rapid communications in mass spectrometry : RCM. 1999; 13(12):1159-64. doi: 10.1002/(sici)1097-0231(19990630)13:12<1159::aid-rcm636>3.0.co;2-#. [PMID: 10390861]
  • D W Loe, K C Almquist, S P Cole, R G Deeley. ATP-dependent 17 beta-estradiol 17-(beta-D-glucuronide) transport by multidrug resistance protein (MRP). Inhibition by cholestatic steroids. The Journal of biological chemistry. 1996 Apr; 271(16):9683-9. doi: 10.1074/jbc.271.16.9683. [PMID: 8621644]
  • S Bellentani, C Armocida, M Pecorari, G Saccoccio, P Marchegiano, A Angeloni, F Manenti, G L Ricci. The role of calcium precipitation in the sulfoglycolithocholate-induced cholestasis of the bile fistula hamster. Journal of hepatology. 1990 May; 10(3):356-63. doi: 10.1016/0168-8278(90)90147-j. [PMID: 2365985]
  • F Kuipers, J P Derksen, A Gerding, G L Scherphof, R J Vonk. Biliary lipid secretion in the rat. The uncoupling of biliary cholesterol and phospholipid secretion from bile acid secretion by sulfated glycolithocholic acid. Biochimica et biophysica acta. 1987 Nov; 922(2):136-44. doi: 10.1016/0005-2760(87)90147-0. [PMID: 3676338]
  • M J Kim, D J Suh. Profiles of serum bile acids in liver diseases. The Korean journal of internal medicine. 1986 Jan; 1(1):37-42. doi: 10.3904/kjim.1986.1.1.37. [PMID: 15759374]
  • R B Kirkpatrick, R A Belsaas. Formation and secretion of glycolithocholate-3-sulfate in primary hepatocyte cultures. Journal of lipid research. 1985 Dec; 26(12):1431-7. doi: . [PMID: 4086945]
  • E R Parise, L B Barbosa, N F Novo, R X Guimarães. [Plasma levels of conjugated bile acids in chronic schistosomal liver diseases]. Revista paulista de medicina. 1984 May; 102(3):113-7. doi: NULL. [PMID: 6474037]
  • A Pagani, A Pranzo, T Galante. [Determination of serum bile acids in hepatobiliary diseases. Clinical applicability]. Minerva medica. 1984 Jan; 75(3-4):99-107. doi: NULL. [PMID: 6700830]
  • A Bremmelgaard, L Ranek, M Bahnsen, P B Andreasen, E Christensen. Cholic acid conjugation test and quantitative liver function in acute liver failure. Scandinavian journal of gastroenterology. 1983 Sep; 18(6):797-802. doi: 10.3109/00365528309182097. [PMID: 6669944]
  • R Santese, C Vai, B Andreuzzi, F Gelosa, A Alberti. [Serum bile acids in chronic liver disease. II: liver cirrhosis]. Giornale di clinica medica. 1983 Jul; 64(7-8):225-33. doi: NULL. [PMID: 6642107]
  • H J Wildgrube, H Stockhausen, P Metz, G Mauritz, R Mahdawi. Radioimmunoassay of bile acids in tissue, bile, and urine. Clinical chemistry. 1983 Mar; 29(3):494-8. doi: . [PMID: 6825261]
  • H J Wildgrube, H Stang, D Schiller, M Winkler, J Weber, H Campana, G Mauritz. [Conjugated bile acids and sulphated glycolithocholic acid in the serum of healthy probands (author's transl)]. Journal of clinical chemistry and clinical biochemistry. Zeitschrift fur klinische Chemie und klinische Biochemie. 1982 May; 20(5):319-23. doi: . [PMID: 7108452]
  • A Esquivel López, G González Espinola, R Gutiérrez Nava, R M García Arreola. [Serum bile acids in hepatobiliary disease]. Revista de gastroenterologia de Mexico. 1982 Jan; 47(1):9-12. doi: NULL. [PMID: 7100761]
  • P Paré, J C Hoefs, M Ashcavai. Determinants of serum bile acids in chronic liver disease. Gastroenterology. 1981 Nov; 81(5):959-64. doi: 10.1016/s0016-5085(81)80125-4. [PMID: 7286574]
  • H Shibata, N Yamada, A Kiyohashi, K Odagiri, K Ishii, H Okabe. [The significance of serum immunoreactive cholylglycine and sulfolithocholylglycine in detection and differential diagnosis of cholelithiasis (author's transl)]. Nihon Shokakibyo Gakkai zasshi = The Japanese journal of gastro-enterology. 1981 Jun; 78(6):1241-7. doi: NULL. [PMID: 7277812]
  • W Bräuninger, K Bork, B Morsches, P Benes, G W Korting. [Pruritus and bile acids. Determination of sulfalithoglycocholate and glycocholate in suction blister fluid and in serum (author's transl)]. Archives of dermatological research. 1981; 270(4):445-52. doi: 10.1007/bf00403789. [PMID: 7283472]
  • J Ohlen, J Richter, A Neiss, M Drescher, H Selmair. [Serum levels of cholylglycine and sulfolitho-cholylglycine in the course of acute hepatitis (author's transl)]. Acta medica Austriaca. 1981; 7(2):49-51. doi: . [PMID: 7211138]
  • L Barbara, R Lazzari, A Roda, R Aldini, D Festi, C Sama, A M Morselli, A Collina, F Bazzoli, G Mazzella, E Roda. Serum bile acids in newborns and children. Pediatric research. 1980 Nov; 14(11):1222-5. doi: 10.1203/00006450-198011000-00014. [PMID: 7454436]
  • D M Collins, G Tisch, C B Campbell. Evaluation of enzymic and radioimmunoassay methods for measuring serum bile acids. Pathology. 1980 Oct; 12(4):623-9. doi: 10.3109/00313028009086815. [PMID: 7465257]
  • R B Kirkpatrick, P G Killenberg. Effects of ethinylestradiol on enzymes catalyzing bile acid conjugation and sulfation. Journal of lipid research. 1980 Sep; 21(7):895-901. doi: 10.1016/s0022-2275(20)34787-8. [PMID: 6934248]
  • Y Oshiumi, S Koga, I Kamoi, H Nishitani, Y Ichiya, H Ibayashi, K Matsuura. [Clinical significance of serum bile acid radioimmunoassay in hepatobiliary diseases--with special reference to the CG/SLCG ratio (author's transl)]. Radioisotopes. 1979 Oct; 28(10):630-5. doi: 10.3769/radioisotopes.28.10_630. [PMID: 531242]
  • H Biffl, R Goebel, G Leb. [The clinical significance of radioimmunologically determined serum bile acids as a new liver function test and the development of a new intravenous sulfolithoglycocholic acid (SLGC) stimulation test]. Acta medica Austriaca. 1979; 6(4):113-20. doi: NULL. [PMID: 552771]