3,7-Dihydroxy-12-oxocholanoic acid
3,7-Dihydroxy-12-oxocholanoic 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. 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 moleclies derived from the catabolism of cholesterol. They modliate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regliation of all the key enzymes involved in cholesterol homeostasis. Bile acids recircliate 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 accumliation in blood and tissues. (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB00400 (3,7-Dihydroxy-12-oxocholanoic acid)
C24H38O5
406.5555
406.271924326
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
12-ketochenodeoxycholic acid
2458-08-4
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)C(=O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C
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/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,22+,23+,24-/m1/s1
MIHNUBCEFJLAGN-DMMBONCOSA-N
Not classified
Expected but not Quantified
Solid
Not Available
Not Available
Not Available
Not Available
None
None
Not Available
Not Available
Not Available
Not Available
FDB022017
Not Available
85044
Not Available
Not Available
Not Available
Not Available
HMDB00400
HMDB00400
5389
94235
Not Available
16312
- Kuramoto T, Furukawa Y, Nishina T, Sugimoto T, Mahara R, Tohma M, Kihira K, Hoshita T: Identification of short side chain bile acids in urine of patients with cerebrotendinous xanthomatosis. J Lipid Res. 1990 Oct;31(10):1895-902. [PubMed:2079611 ]
- St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
- Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
- Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
- Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]
Enzymes
- General function:
- Involved in binding
- Specific function:
- Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
- Gene Name:
- FABP6
- Uniprot ID:
- P51161
- Molecular weight:
- 14371.2
References
- Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
- Gene Name:
- SLCO1B3
- Uniprot ID:
- Q9NPD5
- Molecular weight:
- 77402.2
- General function:
- Involved in transporter activity
- Specific function:
- Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
- Gene Name:
- SLCO1B1
- Uniprot ID:
- Q9Y6L6
- Molecular weight:
- 76448.0
References
- Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]
- General function:
- Involved in ATP binding
- Specific function:
- May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
- Gene Name:
- ABCC3
- Uniprot ID:
- O15438
- Molecular weight:
- 169341.1
- General function:
- Involved in ATP binding
- Specific function:
- Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
- Gene Name:
- ABCB11
- Uniprot ID:
- O95342
- Molecular weight:
- 146405.8
- General function:
- Involved in bile acid:sodium symporter activity
- Specific function:
- Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
- Gene Name:
- SLC10A2
- Uniprot ID:
- Q12908
- Molecular weight:
- 37697.4
References
- Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]
- General function:
- Involved in bile acid:sodium symporter activity
- Specific function:
- The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
- Gene Name:
- SLC10A1
- Uniprot ID:
- Q14973
- Molecular weight:
- 38118.64
- General function:
- Involved in transporter activity
- Specific function:
- Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
- Gene Name:
- SLCO1A2
- Uniprot ID:
- P46721
- Molecular weight:
- 74144.1
- General function:
- Involved in transporter activity
- Specific function:
- Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
- Gene Name:
- SLCO4A1
- Uniprot ID:
- Q96BD0
- Molecular weight:
- 77192.5