Allolithocholic acid (BioDeep_00000018694)

Main id: BioDeep_00000398594

 

human metabolite PANOMIX_OTCML-2023 Endogenous Bile acids BioNovoGene_Lab2019


代谢物信息卡片


(4S)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

化学式: C24H40O3 (376.2977)
中文名称: 石胆酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
InChI: InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)

描述信息

Allolithocholic acid is a bile acid present in normal serum and feces, with a tendency to be at higher concentrations in patients with colon cancer, particularly in men (PMID 16548228). A bile acid. 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).
Allolithocholic acid is a bile acid present in normal serum and feces, with a tendency to be at higher concentrations in patients with colon cancer, particularly in men (PMID 16548228).
D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts
D005765 - Gastrointestinal Agents > D002793 - Cholic Acids
D013501 - Surface-Active Agents > D003902 - Detergents
Lithocholic acid is a toxic secondary bile acid that can promote intrahepatic cholestasis and promote tumorigenesis.

同义名列表

12 个代谢物同义名

(4S)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid; (4S)-4-[(2S,5R,15R)-5-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate; 3a-Hydroxy-5a-cholan-24-Oic acid; 3a-Hydroxy-5a-cholanoic acid; 3a-Hydroxy-5a-cholan-24-Oate; 3-Hydroxycholan-24-oic acid; 3a-Hydroxy-5a-cholanoate; Allolithocholic acid; Allolithocholate; Lithocholic acid; 3α-Hydroxy-5β-cholanic acid; Lithocholic acid



数据库引用编号

21 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 5 ALB, CASP3, CYP3A4, HPGDS, VDR
Endoplasmic reticulum membrane 2 CYP3A4, CYP7A1
Nucleus 5 ALB, CASP3, NR1H4, NR1I2, VDR
cytosol 5 ALB, CASP3, GPT, HPGDS, VDR
nuclear body 1 NR1I2
centrosome 1 ALB
nucleoplasm 5 CASP3, HPGDS, NR1H4, NR1I2, VDR
RNA polymerase II transcription regulator complex 2 NR1H4, VDR
Cell membrane 5 ABCB11, EPHA2, GPRC5A, KCNMA1, TNF
lamellipodium 1 EPHA2
ruffle membrane 1 EPHA2
Multi-pass membrane protein 5 ABCB11, ABCC2, ABCC3, GPRC5A, KCNMA1
cell surface 4 ABCB11, ABCC2, EPHA2, TNF
glutamatergic synapse 1 CASP3
Golgi apparatus 1 ALB
Golgi membrane 2 ABCB11, INS
mitochondrial inner membrane 1 CYP24A1
neuronal cell body 2 CASP3, TNF
endosome 1 ABCB11
plasma membrane 8 ABCB11, ABCC2, ABCC3, EPHA2, GCG, GPRC5A, KCNMA1, TNF
Membrane 6 ABCB11, ABCC2, ABCC3, CYP3A4, EPHA2, KCNMA1
apical plasma membrane 3 ABCB11, ABCC2, KCNMA1
basolateral plasma membrane 1 ABCC3
caveola 1 KCNMA1
extracellular exosome 4 ABCB11, ALB, GPRC5A, GPT
endoplasmic reticulum 1 ALB
extracellular space 5 ALB, GCG, IL6, INS, TNF
intercellular canaliculus 2 ABCB11, ABCC2
mitochondrion 1 CYP24A1
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 4 CYP3A4, CYP7A1, GPRC5A, HPGDS
Microsome membrane 2 CYP3A4, CYP7A1
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 EPHA2
Secreted 4 ALB, GCG, IL6, INS
extracellular region 5 ALB, GCG, IL6, INS, TNF
Single-pass membrane protein 2 CYP7A1, EPHA2
anchoring junction 1 ALB
transcription regulator complex 1 NR1I2
external side of plasma membrane 1 TNF
nucleolus 1 GPRC5A
recycling endosome 2 ABCB11, TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 GPRC5A
postsynaptic membrane 1 KCNMA1
Apical cell membrane 2 ABCB11, ABCC2
Cell projection, ruffle membrane 1 EPHA2
Membrane raft 1 TNF
Cell junction, focal adhesion 1 EPHA2
focal adhesion 1 EPHA2
receptor complex 4 EPHA2, GPRC5A, NR1H4, VDR
ciliary basal body 1 ALB
chromatin 3 NR1H4, NR1I2, VDR
phagocytic cup 1 TNF
[Isoform 3]: Nucleus 1 NR1H4
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
Basolateral cell membrane 1 ABCC3
Recycling endosome membrane 1 ABCB11
endosome lumen 1 INS
leading edge membrane 1 EPHA2
Cytoplasmic vesicle membrane 1 GPRC5A
euchromatin 1 NR1H4
intermediate filament cytoskeleton 1 NR1I2
basal plasma membrane 1 ABCC3
voltage-gated potassium channel complex 1 KCNMA1
secretory granule lumen 2 GCG, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 ALB, GCG, IL6, INS
platelet alpha granule lumen 1 ALB
transport vesicle 1 INS
tight junction 1 EPHA2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
[Isoform 2]: Nucleus 1 NR1H4
[Isoform 1]: Nucleus 1 NR1H4
Basal cell membrane 1 ABCC3
death-inducing signaling complex 1 CASP3
[Isoform 4]: Nucleus 1 NR1H4
intracellular canaliculus 1 ABCB11
lamellipodium membrane 1 EPHA2
[Glucagon-like peptide 1]: Secreted 1 GCG
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
Cell projection, lamellipodium membrane 1 EPHA2
interleukin-6 receptor complex 1 IL6
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

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  • Han-En Tsai, Chia-Ling Chen, Tzu-Ting Chang, Chih-Wei Fu, Wei-Chia Chen, Ser John Lynon P Perez, Pei-Wen Hsiao, Ming-Hong Tai, Wen-Shan Li. Development of a Novel, Potent, and Selective Sialyltransferase Inhibitor for Suppressing Cancer Metastasis. International journal of molecular sciences. 2024 Apr; 25(8):. doi: 10.3390/ijms25084283. [PMID: 38673867]
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  • Anita Wnętrzak, Dawid Szymczuk, Anna Chachaj-Brekiesz, Patrycja Dynarowicz-Latka, Dawid Lupa, Ewelina W Lipiec, Paulina Laszuk, Aneta D Petelska, Karolina H Markiewicz, Agnieszka Z Wilczewska. Lithocholic acid-based oligomers as drug delivery candidates targeting model of lipid raft. Biochimica et biophysica acta. Biomembranes. 2024 Feb; ?(?):184294. doi: 10.1016/j.bbamem.2024.184294. [PMID: 38316379]
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