7-Ketodeoxycholic acid (BioDeep_00000003957)

 

Secondary id: BioDeep_00000408651

human metabolite PANOMIX_OTCML-2023 Endogenous Bile acids


代谢物信息卡片


(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

化学式: C24H38O5 (406.2719)
中文名称: 7-脱氢胆酸, 7-酮-3α,12-α-二羟基胆酸
谱图信息: 最多检出来源 Homo sapiens(feces) 12.45%

分子结构信息

SMILES: CC(CCC(=O)O)C1CCC2C1(C(CC3C2C(=O)CC4C3(CCC(C4)O)C)O)C
InChI: InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-18,20,22,25,27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,20+,22+,23+,24-/m1/s1

描述信息

7-Ketodeoxycholic acid is 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).
7-Ketodeoxycholic acid is a bile acid. 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
7-keto-lithocholic acid is a metabolite of bile acids in Clostridium absonum. 7-keto-lithocholic acid is also converted from Lactobacillus and Bifidobacterium with specific condition[1][2].

同义名列表

44 个代谢物同义名

(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid; (4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,16-Dihydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate; (3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-Oic acid; 3β,12α-Dihydroxy-7-oxo-5α-cholan-24-oic Acid; (3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-Oate; 3 alpha,7 alpha-Dihydroxy-7-keto-5 beta-cholanoic acid; 3alpha,12alpha-Dihydroxy-7-keto-5beta-cholanoic acid; (3a,5b,12a)-3,12-Dihydroxy-7-oxo-cholan-24-Oic acid; (3a,5b,12a)-3,12-Dihydroxy-7-oxocholan-24-Oic acid; 3alpha,12alpha-Dihydroxy-7-oxo-5beta-cholanic acid; 3 alpha,7 alpha-Dihydroxy-7-keto-5 beta-cholanoate; (3Α,5β,12α)-3,12-dihydroxy-7-oxocholan-24-Oic acid; 3 alpha,12 alpha-Diol-7-one-5 beta-cholanoic acid; 3alpha,12alpha-Dihydroxy-7-keto-5beta-cholanoate; 7-Ketodeoxycholic acid, (3alpha,12alpha)-isomer; (3a,5b,12a)-3,12-Dihydroxy-7-oxo-cholan-24-Oate; 3alpha,12alpha-Dihydroxy-7-oxo-5beta-cholanate; (3a,5b,12a)-3,12-Dihydroxy-7-oxocholan-24-Oate; 3alpha,12alpha-Diol-7-one-5beta-cholanoic acid; (3Α,5β,12α)-3,12-dihydroxy-7-oxocholan-24-Oate; 3 alpha,12 alpha-Diol-7-one-5 beta-cholanoate; 3a,12a-Dihydroxy-7-oxo-5b-cholan-24-Oic acid; 3alpha,12alpha-Diol-7-one-5beta-cholanoate; 3a,12a-Dihydroxy-7-keto-5b-cholanoic acid; 3Α,12α-dihydroxy-7-keto-5β-cholanoic acid; 3a,12a-Dihydroxy-7-oxo-5b-cholan-24-Oate; 3Α,12α-dihydroxy-7-oxo-5β-cholanic acid; 3a,12a-Dihydroxy-7-oxo-5b-cholanic acid; 3Α,12α-dihydroxy-7-keto-5β-cholanoate; 7-Keto-3α,12-α-dihydroxycholanic Acid; 3a,12a-Dihydroxy-7-keto-5b-cholanoate; 3Α,12α-diol-7-one-5β-cholanoic acid; 3a,12a-Diol-7-one-5b-cholanoic acid; 3a,12a-Dihydroxy-7-oxo-5b-cholanate; 3Α,12α-dihydroxy-7-oxo-5β-cholanate; 3Α,12α-diol-7-one-5β-cholanoate; 3a,12a-Diol-7-one-5b-cholanoate; 7-Cheto-deoxycholic acid; 7-Ketodeoxycholic acid; 7-Oxodeoxycholic acid; 7-Ketodeoxycholate; 7-Oxodeoxycholate; 7-Dehydrocholic acid (7-DHCA); 7-keto-Deoxycholic acid



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

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

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Plant Reactome(0)

INOH(0)

PlantCyc(0)

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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。

亚细胞结构定位 关联基因列表
Cytoplasm 7 BDNF, CMPK2, CYP1A1, MARVELD1, NTRK2, TJP1, TRIB1
Peripheral membrane protein 5 ALOX15, COG2, CYP1A1, PLA2G2F, TJP1
Endosome membrane 1 NTRK2
Endoplasmic reticulum membrane 3 CYP1A1, HSD17B7, TKT
Nucleus 3 MARVELD1, TJP1, TRIB1
cytosol 7 ALOX15, GPT, NTRK2, PLA2G2F, TJP1, TKT, TRIB1
dendrite 2 BDNF, NTRK2
nuclear body 1 TKT
nucleoplasm 2 CMPK2, TKT
Cell membrane 7 ALOX15, CLDN1, MARVELD1, NTRK2, TJP1, TKT, TNF
Cytoplasmic side 2 COG2, TJP1
Cell projection, axon 1 NTRK2
Early endosome membrane 1 NTRK2
Multi-pass membrane protein 2 CLDN1, MARVELD1
Golgi apparatus membrane 1 COG2
cell junction 1 TJP1
cell surface 1 TNF
Golgi apparatus 1 COG2
Golgi membrane 1 COG2
mitochondrial inner membrane 2 CYP1A1, SQOR
neuronal cell body 1 TNF
synaptic vesicle 1 BDNF
Cytoplasm, cytosol 1 ALOX15
plasma membrane 8 ALOX15, CLDN1, MARVELD1, NTRK2, PLA2G2F, TJP1, TKT, TNF
terminal bouton 1 NTRK2
Membrane 6 ALOX15, BDNF, CLDN1, COG2, MARVELD1, NTRK2
apical plasma membrane 3 CLDN1, TJP1, TKT
axon 2 BDNF, NTRK2
basolateral plasma membrane 2 CLDN1, TJP1
extracellular exosome 2 GPT, TKT
extracellular space 4 BDNF, IL10, IL6, TNF
perinuclear region of cytoplasm 2 BDNF, NTRK2
Cell junction, tight junction 2 CLDN1, TJP1
adherens junction 1 TJP1
apicolateral plasma membrane 1 TJP1
bicellular tight junction 2 CLDN1, TJP1
gap junction 1 TJP1
intercalated disc 1 TJP1
intercellular canaliculus 1 TJP1
mitochondrion 5 CMPK2, CYP1A1, HSD17B7, SQOR, TJP1
protein-containing complex 2 CLDN1, TJP1
intracellular membrane-bounded organelle 1 CYP1A1
Microsome membrane 1 CYP1A1
postsynaptic density 1 NTRK2
Single-pass type I membrane protein 2 NTRK2, TKT
Secreted 3 BDNF, IL10, IL6
extracellular region 5 BDNF, IL10, IL6, PLA2G2F, TNF
cytoplasmic side of plasma membrane 1 ALOX15
Single-pass membrane protein 1 HSD17B7
external side of plasma membrane 1 TNF
actin cytoskeleton 1 TKT
dendritic spine 1 NTRK2
Early endosome 1 NTRK2
apical part of cell 1 TJP1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 TKT
Cytoplasm, perinuclear region 1 NTRK2
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 MARVELD1
focal adhesion 1 TKT
Peroxisome 1 TKT
lateral plasma membrane 1 CLDN1
receptor complex 2 NTRK2, TKT
cell projection 1 TJP1
phagocytic cup 1 TNF
cytoskeleton 1 MARVELD1
Cell projection, podosome 1 TJP1
podosome 1 TJP1
Basolateral cell membrane 1 CLDN1
Lipid droplet 1 ALOX15
Cell projection, dendrite 1 NTRK2
trans-Golgi network membrane 1 COG2
Golgi stack 1 COG2
endoplasmic reticulum lumen 2 BDNF, IL6
axon terminus 1 NTRK2
tight junction 2 CLDN1, TJP1
apical junction complex 1 TJP1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform 1]: Secreted 1 PLA2G2F
interleukin-6 receptor complex 1 IL6
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
Golgi transport complex 1 COG2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • 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]
  • Satoru Fukiya, Miki Arata, Hiroko Kawashima, Daisuke Yoshida, Maki Kaneko, Kimiko Minamida, Jun Watanabe, Yoshio Ogura, Kiyohisa Uchida, Kikuji Itoh, Masaru Wada, Susumu Ito, Atsushi Yokota. Conversion of cholic acid and chenodeoxycholic acid into their 7-oxo derivatives by Bacteroides intestinalis AM-1 isolated from human feces. FEMS microbiology letters. 2009 Apr; 293(2):263-70. doi: 10.1111/j.1574-6968.2009.01531.x. [PMID: 19243441]
  • Y Amuro, T Endo, K Higashino, K Uchida, Y Yamamura. Urinary and fecal keto bile acids in liver cirrhosis. Clinica chimica acta; international journal of clinical chemistry. 1981 Aug; 114(2-3):137-47. doi: 10.1016/0009-8981(81)90387-9. [PMID: 7285341]
  • L J Haeffner, S J Gordon, J S Magen, O D Kowlessar. Evaluation of the 3 alpha-hydroxysteroid dehydrogenase assay for ursodeoxycholic acid, and 7 oxo- and 12 oxo- bile acids. Journal of lipid research. 1980 May; 21(4):477-80. doi: . [PMID: 6929859]
  • M Morotomi, Y Kawai, M Mutai. Intestinal microflora and bile acids. In vitro cholic acid transformation by mixed fecal culture of rats. Microbiology and immunology. 1979; 23(9):839-47. doi: 10.1111/j.1348-0421.1979.tb02817.x. [PMID: 43948]