3a,7a-Dihydroxycholanoic acid
3a,7a-Dihydroxycholanoic acid is a chenodeoxycholic or bile acid present in human blood serum. (PMID 13324110 ) and in the biliary excretion of patients with choledochostomy drainage (PMID 16695472 ). 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.
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB00384 (3a,7a-Dihydroxycholanoic acid)
C24H40O4
392.572
392.292659768
(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
3a,7a-dihydroxycholanoate
30634-99-2
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15?,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
RUDATBOHQWOJDD-BYRKYSOESA-N
Not classified
Expected but not Quantified
Solid
Not Available
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None
None
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FDB022002
Not Available
13628074
Not Available
Not Available
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Not Available
HMDB00384
HMDB00384
5373
21252245
Not Available
Not Available
- CAREY JB Jr: Chenodeoxycholic acid in human blood serum. Science. 1956 May 18;123(3203):892. [PubMed:13324110 ]
- WYSOCKI AP, PORTMAN OW, MANN GV: Bile acids in blood: methods and their application to studies of experimental atherosclerosis in monkeys. Arch Biochem Biophys. 1955 Nov;59(1):213-23. [PubMed:13269172 ]
- Johnston CG, Irvin JL: THE BILIARY EXCRETION OF VARIOUS BILE ACIDS BY PATIENTS WITH CHOLEDOCHOSTOMY DRAINAGE, AND THE EFFECT OF ORAL ADMINISTRATION OF DESICCATED BILE OF THE OX AND THE HOG. J Clin Invest. 1947 Jul;26(4):802-14. [PubMed:16695472 ]
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