Glycolithocholate (BioDeep_00000003937)

 

Secondary id: BioDeep_00001871906

human metabolite Endogenous blood metabolite Bile acids PANOMIX LipidSearch


代谢物信息卡片


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

化学式: C26H43NO4 (433.3192)
中文名称: 甘氨石胆酸
谱图信息: 最多检出来源 Homo sapiens(feces) 29.49%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Glycolithocholate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/glycolithocholate (retrieved 2025-01-07) (BioDeep RN: BioDeep_00000003937). 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)O)C)C
InChI: InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

描述信息

Lithocholic acid glycine conjugate is an acyl glycine and a bile acid-glycine conjugate. 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). Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487, 16037564, 12576301, 11907135).
Lithocholic acid glycine conjugate is an acyl glycine and a bile acid-glycine conjugate. 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). Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12.
D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts
D005765 - Gastrointestinal Agents > D002793 - Cholic Acids

同义名列表

43 个代谢物同义名

2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[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)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid; 3alpha-Hydroxy-5beta-cholan-24-Oic acid N-(carboxymethyl)amide; N-[(3alpha,5beta)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycine; N-((3-alpha,5-beta)-3-Hydroxy-24-oxocholan-24-yl)glycine; N-[(3alpha,5beta)-3-hydroxy-24-oxocholan-24-yl]-glycine; N-[(3α,5β)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycine; N-((3-Α,5-β)-3-hydroxy-24-oxocholan-24-yl)glycine; N-((3-a,5-b)-3-Hydroxy-24-oxocholan-24-yl)glycine; 3alpha-Hydroxy-5beta-cholanoylglycine 3-sulphate; N-(Carboxymethyl)-3a-hydroxy-5b-cholan-24-amide; 3a-Hydroxy-N-(carboxymethyl)-5b-cholan-24-amide; 3alpha-Hydroxy-5beta-cholanoylglycine 3-sulfate; 3α-Hydroxy-5β-cholanoylglycine 3-sulphate; 3a-Hydroxy-5b-cholanic acid glycine ester; 3α-Hydroxy-5β-cholanoylglycine 3-sulfate; N-(3a-Hydroxy-5b-cholan-24-oyl)-glycine; 3alpha-Hydroxy-5beta-cholan-24-oic Acid; Glycolithocholic acid, monosodium salt; Lithocholic acid glycine conjugic acid; Glycolithocholic acid 3alpha-sulphate; Glycolithocholic acid 3alpha-sulfate; 3alpha-Hydroxy-5beta-cholan-24-Oate; N-(3a-Hydroxy-5b-cholanoyl)glycine; Lithocholic acid glycine conjugate; Glycolithocholic acid 3α-sulphate; Glycolithocholic acid 3-sulphate; Glycolithocholic acid 3α-sulfate; Glycolithocholic acid 3-sulfate; Lithocholate glycine conjugate; 3a-Hydroxy-5b-cholanoylglycine; Glycolithocholic acid sulphate; Glycolithocholic acid sulfate; Sulfoglycolithocholic acid; Sulfolithocholylglycine; Glycolithocholic acid; Lithocholoyglycine; Lithocholylglycine; Glycolithocholate; ST 24:1;O3;G; AC1N3NBH; Glycolithocholic acid (GLCA); Glycolithocholate



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)

2 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
Cytoplasm 10 ALB, ANXA2, CPOX, FOXO3, GPBAR1, HPGDS, NR1I3, PKHD1, PRKAA2, SULT1E1
Peripheral membrane protein 1 FOXO3
Endoplasmic reticulum membrane 2 CD4, SLC51A
Nucleus 6 ALB, ANXA2, FOXO3, NR1I3, PKHD1, PRKAA2
cytosol 8 ALB, ANXA2, CPOX, FOXO3, HPGDS, NR1I3, PRKAA2, SULT1E1
dendrite 1 PRKAA2
centrosome 2 ALB, PKHD1
nucleoplasm 4 FOXO3, HPGDS, NR1I3, PRKAA2
RNA polymerase II transcription regulator complex 1 ANXA2
Cell membrane 7 CD4, CD8A, GPBAR1, PKHD1, SLC51A, SLCO1B1, SLCO1B3
Cytoplasmic side 1 FOXO3
Multi-pass membrane protein 5 GPBAR1, SLC25A13, SLC51A, SLCO1B1, SLCO1B3
cell surface 1 ANXA2
glutamatergic synapse 1 GHRL
Golgi apparatus 3 ALB, PKHD1, PRKAA2
Golgi membrane 1 INS
lysosomal membrane 1 ANXA2
mitochondrial inner membrane 1 SLC25A13
neuronal cell body 1 PRKAA2
postsynapse 1 GHRL
sarcolemma 1 ANXA2
Cytoplasm, cytosol 2 FOXO3, SULT1E1
endosome 1 ANXA2
plasma membrane 8 ANXA2, CD4, CD8A, GPBAR1, SLC25A13, SLC51A, SLCO1B1, SLCO1B3
Membrane 6 ANXA2, CPOX, PRKAA2, SLC51A, SLCO1B1, SLCO1B3
apical plasma membrane 1 PKHD1
axon 2 GHRL, PRKAA2
basolateral plasma membrane 4 ANXA2, SLC51A, SLCO1B1, SLCO1B3
extracellular exosome 4 ALB, ANXA2, BMP3, PKHD1
endoplasmic reticulum 2 ALB, PKHD1
extracellular space 6 ALB, ANXA2, BMP3, CRP, GHRL, INS
perinuclear region of cytoplasm 1 PKHD1
Schaffer collateral - CA1 synapse 1 GHRL
adherens junction 1 ANXA2
mitochondrion 2 CPOX, SLC25A13
protein-containing complex 3 ALB, FOXO3, SLC51A
intracellular membrane-bounded organelle 1 HPGDS
Single-pass type I membrane protein 3 CD4, CD8A, PKHD1
Secreted 6 ALB, BMP3, CRP, GHRL, INS, PKHD1
extracellular region 7 ALB, ANXA2, BMP3, CD8A, CRP, GHRL, INS
Mitochondrion outer membrane 1 FOXO3
mitochondrial outer membrane 1 FOXO3
[Isoform 2]: Secreted 1 CD8A
Mitochondrion matrix 1 FOXO3
mitochondrial matrix 1 FOXO3
anchoring junction 1 ALB
Cell projection, cilium 1 PKHD1
nuclear membrane 1 SULT1E1
external side of plasma membrane 3 CD4, CD8A, PKHD1
neuronal dense core vesicle lumen 1 GHRL
midbody 1 ANXA2
Early endosome 2 ANXA2, CD4
vesicle 1 ANXA2
Apical cell membrane 1 PKHD1
Mitochondrion inner membrane 1 SLC25A13
Membrane raft 1 CD4
Cytoplasm, cytoskeleton 1 NR1I3
Cytoplasm, cytoskeleton, spindle 1 PKHD1
basement membrane 1 ANXA2
Mitochondrion intermembrane space 1 SLC25A13
mitochondrial intermembrane space 2 CPOX, SLC25A13
collagen-containing extracellular matrix 1 ANXA2
nuclear speck 1 PRKAA2
receptor complex 2 CD8A, GPBAR1
ciliary basal body 2 ALB, PKHD1
cilium 1 PKHD1
chromatin 2 FOXO3, NR1I3
Late endosome membrane 1 ANXA2
mitotic spindle 1 PKHD1
cytoskeleton 1 NR1I3
Cytoplasm, cytoskeleton, cilium basal body 1 PKHD1
centriole 1 ALB
plasma membrane protein complex 1 ANXA2
spindle pole 1 ALB
blood microparticle 1 ALB
Basolateral cell membrane 2 SLCO1B1, SLCO1B3
endosome lumen 1 INS
Lipid droplet 1 ANXA2
Cornified envelope 1 ANXA2
Chromosome, centromere 1 PKHD1
Melanosome 1 ANXA2
cytoplasmic stress granule 1 PRKAA2
basal plasma membrane 2 SLCO1B1, SLCO1B3
plasma membrane raft 1 CD8A
secretory granule lumen 2 GHRL, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 ALB, CD4, GHRL, INS
nuclear matrix 1 ANXA2
platelet alpha granule lumen 1 ALB
transport vesicle 1 INS
RNA polymerase II transcription repressor complex 1 FOXO3
Schmidt-Lanterman incisure 1 ANXA2
Secreted, extracellular exosome 1 PKHD1
azurophil granule lumen 1 ANXA2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
chromosome, centromeric region 1 PKHD1
9+0 non-motile cilium 1 PKHD1
vesicle membrane 1 ANXA2
clathrin-coated endocytic vesicle membrane 1 CD4
Basal cell membrane 2 SLCO1B1, SLCO1B3
[Isoform 1]: Cell membrane 1 CD8A
nucleotide-activated protein kinase complex 1 PRKAA2
Secreted, extracellular space, extracellular matrix, basement membrane 1 ANXA2
T cell receptor complex 2 CD4, CD8A
AnxA2-p11 complex 1 ANXA2
myelin sheath adaxonal region 1 ANXA2
PCSK9-AnxA2 complex 1 ANXA2
ciliary transition fiber 1 ALB


文献列表

  • Xingguo Cheng, Youcai Zhang, Curtis D Klaassen. Decreased bile-acid synthesis in livers of hepatocyte-conditional NADPH-cytochrome P450 reductase-null mice results in increased bile acids in serum. The Journal of pharmacology and experimental therapeutics. 2014 Oct; 351(1):105-13. doi: 10.1124/jpet.114.216796. [PMID: 25034404]
  • Carlos A Penno, Stuart A Morgan, Adam J Rose, Stephan Herzig, Gareth G Lavery, Alex Odermatt. 11β-Hydroxysteroid dehydrogenase-1 is involved in bile acid homeostasis by modulating fatty acid transport protein-5 in the liver of mice. Molecular metabolism. 2014 Aug; 3(5):554-64. doi: 10.1016/j.molmet.2014.04.008. [PMID: 25061560]
  • Rima Kaddurah-Daouk, Rebecca A Baillie, Hongjie Zhu, Zhao-Bang Zeng, Michelle M Wiest, Uyen Thao Nguyen, Katie Wojnoonski, Steven M Watkins, Miles Trupp, Ronald M Krauss. Enteric microbiome metabolites correlate with response to simvastatin treatment. PloS one. 2011; 6(10):e25482. doi: 10.1371/journal.pone.0025482. [PMID: 22022402]
  • Jocelyn Trottier, Andrzej Białek, Patrick Caron, Robert J Straka, Piotr Milkiewicz, Olivier Barbier. Profiling circulating and urinary bile acids in patients with biliary obstruction before and after biliary stenting. PloS one. 2011; 6(7):e22094. doi: 10.1371/journal.pone.0022094. [PMID: 21760958]
  • Anand Balakrishnan, Stephen A Wring, James E Polli. Interaction of native bile acids with human apical sodium-dependent bile acid transporter (hASBT): influence of steroidal hydroxylation pattern and C-24 conjugation. Pharmaceutical research. 2006 Jul; 23(7):1451-9. doi: 10.1007/s11095-006-0219-4. [PMID: 16783481]
  • DebraLynn Mims, David Hercules. Quantification of bile acids directly from plasma by MALDI-TOF-MS. Analytical and bioanalytical chemistry. 2004 Mar; 378(5):1322-6. doi: 10.1007/s00216-003-2475-z. [PMID: 14747894]
  • Maria Rius, Anne T Nies, Johanna Hummel-Eisenbeiss, Gabriele Jedlitschky, Dietrich Keppler. Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. Hepatology (Baltimore, Md.). 2003 Aug; 38(2):374-84. doi: 10.1053/jhep.2003.50331. [PMID: 12883481]
  • DebraLynn Mims, David Hercules. Quantification of bile acids directly from urine by MALDI-TOF-MS. Analytical and bioanalytical chemistry. 2003 Mar; 375(5):609-16. doi: 10.1007/s00216-003-1771-y. [PMID: 12638043]
  • 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]
  • Kunrong Cheng, Sandeep Khurana, Ying Chen, Richard H Kennedy, Piotr Zimniak, Jean-Pierre Raufman. Lithocholylcholine, a bile acid/acetylcholine hybrid, is a muscarinic receptor antagonist. The Journal of pharmacology and experimental therapeutics. 2002 Oct; 303(1):29-35. doi: 10.1124/jpet.102.036376. [PMID: 12235229]
  • M R Leonard, M A Bogle, M C Carey, J M Donovan. Spread monomolecular films of monohydroxy bile acids and their salts: influence of hydroxyl position, bulk pH, and association with phosphatidylcholine. Biochemistry. 2000 Dec; 39(51):16064-74. doi: 10.1021/bi001316m. [PMID: 11123934]
  • T Washizu, T Ishida, M Washizu, I Tomoda, J J Kaneko. Changes in bile acid composition of serum and gallbladder bile in bile duct ligated dogs. The Journal of veterinary medical science. 1994 Apr; 56(2):299-303. doi: 10.1292/jvms.56.299. [PMID: 8075218]
  • F Kuipers, M Enserink, R Havinga, A B van der Steen, M J Hardonk, J Fevery, R J Vonk. Separate transport systems for biliary secretion of sulfated and unsulfated bile acids in the rat. The Journal of clinical investigation. 1988 May; 81(5):1593-9. doi: 10.1172/jci113493. [PMID: 3366909]
  • 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]
  • S Barnes, R Waldrop, J Crenshaw, R J King, K B Taylor. Evidence for an ordered reaction mechanism for bile salt: 3'phosphoadenosine-5'-phosphosulfate: sulfotransferase from rhesus monkey liver that catalyzes the sulfation of the hepatotoxin glycolithocholate. Journal of lipid research. 1986 Nov; 27(11):1111-23. doi: . [PMID: 3470420]
  • J Yanagisawa, Y Akashi, H Miyazaki, F Nakayama. Critical evaluation of the existence of so-called tissue-bound lithocholate in human liver tissue by selected ion monitoring. Journal of lipid research. 1984 Nov; 25(11):1263-71. doi: 10.1016/s0022-2275(20)40778-3. [PMID: 6394682]
  • A K Batta, S Shefer, G Salen. Thin-layer chromatographic separation of conjugates of ursodeoxycholic acid from those of litho-, chenodeoxy-, deoxy-, and cholic acids. Journal of lipid research. 1981 May; 22(4):712-4. doi: ". [PMID: 7276746]
  • L J Chen. Bile salt sulfotransferase. Methods in enzymology. 1981; 77(?):213-8. doi: 10.1016/s0076-6879(81)77028-9. [PMID: 6948990]