12-ketolithocholic acid profile

12-ketolithocholic acid (12-KLCA) is a **secondary bile acid** that is produced in the gut by the bacterial metabolism of primary bile acids, namely cholic acid and chenodeoxycholic acid.

Here's why it's important for research:

**1. Role in Gut Microbiome and Liver Disease:**

* **Altered gut microbiome:** 12-KLCA is a marker for dysbiosis, an imbalance in the gut microbiome. Studies have linked high levels of 12-KLCA to gut dysbiosis and conditions like inflammatory bowel disease (IBD).
* **Liver disease:** Elevated 12-KLCA is associated with liver disease, including non-alcoholic fatty liver disease (NAFLD) and cirrhosis. It contributes to liver inflammation and fibrosis by activating specific signaling pathways.

**2. Potential Therapeutic Targets:**

* **Anti-inflammatory effects:** 12-KLCA has shown anti-inflammatory properties in some studies, suggesting potential therapeutic use in conditions like IBD.
* **Modulating gut microbiota:** Research is exploring the use of 12-KLCA to manipulate the gut microbiome, potentially improving gut health and reducing the risk of associated diseases.
* **Liver disease treatment:** Further research is investigating 12-KLCA's role in liver disease progression and its potential as a therapeutic target for reducing liver inflammation and fibrosis.

**3. Research Tool:**

* **Biomarker for gut health:** 12-KLCA levels can be used as a non-invasive marker to assess gut health and identify potential risk factors for diseases.
* **Understanding gut-liver axis:** Studying 12-KLCA provides insights into the complex relationship between the gut microbiome and liver health, potentially leading to better disease prevention and treatment strategies.

**Important to Note:**

* While 12-KLCA shows promise in research, its precise role and clinical significance are still being investigated.
* More research is needed to fully understand its mechanisms of action, therapeutic potential, and potential risks.

**Overall, 12-KLCA is a fascinating molecule that offers valuable insights into gut health, liver disease, and the complex interplay between the microbiome and host physiology. Research on 12-KLCA continues to contribute to our understanding of these areas and potentially pave the way for new diagnostic and therapeutic approaches.**

12-ketolithocholic acid: RN given refers to (3alpha,5beta)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	3080612
CHEMBL ID	1254076
CHEBI ID	139134
SCHEMBL ID	1176911
MeSH ID	M0099987

Synonym
unii-57668172z5
57668172z5 ,
5130-29-0
3alpha-hydroxy-12-oxo-5beta-cholan-24-oic acid
LMST04010155
12-ketolithocholic acid
3alpha-hydroxy-12-0x0-5beta-cholanoic acid
cholan-24-oic acid, 3-hydroxy-12-oxo-, (3alpha,5beta)-
ccris 3990
CHEBI:139134
(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-12-oxo-1,2,3,4,5,6,7,8,9,11,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
CHEMBL1254076
3.alpha.-hydroxy-12-0x0-5.beta.-cholanoic acid
12-oxolithocholic acid
12-dehydrodeoxycholic acid
cholan-24-oic acid, 3-hydroxy-12-oxo-, (3.alpha.,5.beta.)-
12-ketodeoxycholic acid
SCHEMBL1176911
12-oxo-3.alpha.-hydroxy-5.beta.-cholanic acid
CVNYHSDFZXHMMJ-VPUMZWJWSA-N
12-keto-lca
DTXSID80199300
AKOS030532130
3a-hydroxy-12-oxo-5b-cholan-24-oate
3a-hydroxy-12-oxo-5b-cholanic acid
12-ketolithocholate
3a-hydroxy-12-oxo-5b-cholan-24-oic acid
3a-hydroxy-12-oxo-5b-cholanoic acid
(3a,5b)-3-hydroxy-12-oxo-cholan-24-oic acid
3a-hydroxy-12-oxo-5b-cholanate
(3alpha,5beta)-3-hydroxy-12-oxo-cholan-24-oic acid
12-oxo-3a-hydroxy-5b-cholanate
12-ketodeoxycholate
12-dehydrodeoxycholate
(3a,5b)-3-hydroxy-12-oxo-cholan-24-oate
(3alpha,5beta)-3-hydroxy-12-oxo-cholan-24-oate
12-oxo-3a-hydroxy-5b-cholanic acid
3a-hydroxy-12-oxo-5b-cholanoate
12-oxolithocholate
HY-135772
3-alpha-hydroxy-12-oxo-5-beta-cholanoic acid
3?-hydroxy-12 ketolithocholic acid
Q27261472
CS-0113974
5beta-cholanic acid-3alpha-ol-12-one
1ST161151
baa485
(r)-4-((3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-12-oxohexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic acid
PD131171
(3alpha,5beta)-3-hydroxy-12-oxocholan-24-oic acid
E83722
(4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-7-hydroxy-9a,11a-dimethyl-11-oxo-hexadecahydro-1h-cyclopenta[a]phenanthren-1-yl]pentanoic acid

Excerpt	Reference	Relevance
" Finally, CDCA, DCA and LagoDCA were prominent outliers being more toxic than predicted by RMw."	( Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A). Gilmer, JF; Keaveney, R; Kelleher, D; Long, A; Majer, F; Peta, VK; Sharma, R; Wang, J, 2010)	0.36

Class	Description
bile acid	Any member of a group of hydroxy-5beta-cholanic acids occuring in bile, where they are present as the sodium salts of their amides with glycine or taurine. In mammals bile acids almost invariably have 5beta-configuration.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Assay ID	Title	Year	Journal	Article
AID515398	Cytotoxicity against human HET-1A cells assessed as cell viability after 24 hrs by MTT assay	2010	Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18	Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
AID515399	Cytotoxicity against human HuH7 cells assessed as cell viability at 500 uM after 24 hrs by MTT assay relative to control	2010	Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18	Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
AID515400	Cytotoxicity against human HET-1A cells assessed as cell viability at 500 uM after 24 hrs by MTT assay relative to control	2010	Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18	Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (60.00)	18.7374
1990's	1 (20.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	1 (20.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	5 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
dehydrocholic acid Dehydrocholic Acid: A semisynthetic bile acid made from cholic acid. It is used as a cholagogue, hydrocholeretic, diuretic, and as a diagnostic aid.. 3,7,12-trioxo-5beta-cholanic acid : An oxo-5beta-cholanic acid in which three oxo substituents are located at positions 3, 7 and 12 on the cholanic acid skeleton.	2.05	1	12-oxo steroid; 3-oxo-5beta-steroid; 7-oxo steroid; oxo-5beta-cholanic acid	gastrointestinal drug
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	2.05	1	amino sulfonic acid; bile acid taurine conjugate	human metabolite
lithocholic acid Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.. lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.. lithocholate : A bile acid anion that is the conjugate base of lithocholic acid.	3.99	5	bile acid; C24-steroid; monohydroxy-5beta-cholanic acid	geroprotector; human metabolite; mouse metabolite
chenodeoxycholic acid Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.. chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.. chenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.	2.39	2	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
glycocholic acid Glycocholic Acid: The glycine conjugate of CHOLIC ACID. It acts as a detergent to solubilize fats for absorption and is itself absorbed.. glycocholic acid : A bile acid glycine conjugate having cholic acid as the bile acid component.. glycocholate : A cholanic acid conjugate anion that is the conjugate base of glycocholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.05	1	bile acid glycine conjugate	human metabolite
glycochenodeoxycholic acid Glycochenodeoxycholic Acid: A bile salt formed in the liver from chenodeoxycholate and glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic.. glycochenodeoxycholate : A N-acylglycinate that is the conjugate base of glycochenodeoxycholic acid.. glycochenodeoxycholic acid : A bile acid glycine conjugate having 3alpha,7alpha-dihydroxy-5beta-cholan-24-oyl as the bile acid component.	2.05	1	bile acid glycine conjugate	human metabolite
ursodeoxycholic acid Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.05	1	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
3,7-dihydroxy-12-oxocholanoic acid 3,7-dihydroxy-12-oxocholanoic acid: RN given refers to (3alpha,5beta,7alpha)-isomer	1.96	1	oxo-5beta-cholanic acid
ursocholic acid ursocholic acid: see also records for allocholic and cholic acids. ursocholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three hydroxy substituents at positions 3alpha, 7beta and 12alpha.	2.05	1	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7beta-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	EC 1.1.1.159 (7alpha-hydroxysteroid dehydrogenase) inhibitor; human urinary metabolite
7-ketodeoxycholic acid 7-ketodeoxycholic acid: RN given refers to (3 alpha,5 beta,12 alpha)-isomer	1.96	1	7-oxo steroid; oxo-5beta-cholanic acid
24-norursodeoxycholic acid 24-norursodeoxycholic acid: structure given in first source	2.05	1
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	2.05	1	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
deoxycholic acid Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.	2.67	3	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
Deoxycholic acid methyl ester [no description available]	2.05	1	cholanoid
taurochenodeoxycholic acid Taurochenodeoxycholic Acid: A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic.. taurochenodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurochenodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. taurochenodeoxycholic acid : A bile acid taurine conjugate of chenodeoxycholic acid.	2.05	1	bile acid taurine conjugate	human metabolite; mouse metabolite
7-ketolithocholic acid 7-ketolithocholic acid: RN given refers to (3alpha,5beta)-isomer. 7-oxolithocholic acid : A bile acid that is lithocholic acid carrying an additional oxo substituent at position 7.	2.05	1	3alpha-hydroxy steroid; bile acid; monohydroxy-5beta-cholanic acid; oxo-5beta-cholanic acid	human metabolite
sodium taurodeoxycholate Taurodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. It is used as a cholagogue and choleretic, also industrially as a fat emulsifier.. taurodeoxycholic acid : A bile acid taurine conjugate of deoxycholic acid.. taurodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurodeoxycholic acid.	2.05	1	bile acid taurine conjugate	human metabolite
nadp [no description available]	1.97	1
glycodeoxycholic acid Glycodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic.. glycodeoxycholic acid : A bile acid glycine conjugate of deoxycholic acid.	2.05	1	bile acid glycine conjugate	human metabolite
hyodeoxycholic acid hyodeoxycholic acid: differs from deoxycholic acid in that the 6 alpha-OH is in the 12 position in the former; RN given refers to (3alpha,5beta,6alpha)-isomer. hyodeoxycholic acid : A member of the class of 5beta-cholanic acids that is (5beta)-cholan-24-oic acid substituted by alpha-hydroxy groups at positions 3 and 6.	2.05	1	5beta-cholanic acids; 6alpha,20xi-murideoxycholic acid; bile acid; C24-steroid	human metabolite; mouse metabolite
ursodoxicoltaurine tauroursodeoxycholate : An organosulfonate oxoanion that is the conjugate base of tauroursodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. tauroursodeoxycholic acid : A bile acid taurine conjugate derived from ursoodeoxycholic acid.	2.05	1	bile acid taurine conjugate	anti-inflammatory agent; apoptosis inhibitor; bone density conservation agent; cardioprotective agent; human metabolite; neuroprotective agent
glycoursodeoxycholic acid glycoursodeoxycholic acid : A bile acid glycine conjugate derived from ursoodeoxycholic acid.. glycoursodeoxycholate : A N-acylglycinate that is the conjugate base of glycoursodeoxycholic acid. obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.05	1	bile acid glycine conjugate; N-acylglycine	human blood serum metabolite; neuroprotective agent

Condition	Relationship Strength	Studies
Esophageal Varices [description not available]	1.96	1
Encephalopathy, Hepatic [description not available]	1.96	1
Cirrhosis, Liver [description not available]	1.96	1
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	1.96	1
Esophageal and Gastric Varices Dilated blood vessels in the ESOPHAGUS or GASTRIC FUNDUS that shunt blood from the portal circulation (PORTAL SYSTEM) to the systemic venous circulation. Often they are observed in individuals with portal hypertension (HYPERTENSION, PORTAL).	1.96	1
Hepatic Encephalopathy A syndrome characterized by central nervous system dysfunction in association with LIVER FAILURE, including portal-systemic shunts. Clinical features include lethargy and CONFUSION (frequently progressing to COMA); ASTERIXIS; NYSTAGMUS, PATHOLOGIC; brisk oculovestibular reflexes; decorticate and decerebrate posturing; MUSCLE SPASTICITY; and bilateral extensor plantar reflexes (see REFLEX, BABINSKI). ELECTROENCEPHALOGRAPHY may demonstrate triphasic waves. (From Adams et al., Principles of Neurology, 6th ed, pp1117-20; Plum & Posner, Diagnosis of Stupor and Coma, 3rd ed, p222-5)	1.96	1
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	1.96	1
Autoimmune Diabetes [description not available]	2.88	1
Diabetes Mellitus, Adult-Onset [description not available]	2.88	1
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	2.88	1
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	2.88	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.88	1

12-ketolithocholic acid

Description

Cross-References

Synonyms (52)

Research Excerpts

Toxicity

Drug Classes (1)

Bioassays (3)

Research

Studies (5)

Market Indicators

Research Demand Index: 12.42

Study Types