7a-Hydroxy-3-oxo-5b-cholanoic acid
Glycine- and taurine-conjugated 7 alpha-hydroxy-3-oxo-5 beta-cholanoic acid has been identified in normal human serum (PMID 1939467 ) and as a cholesterol metabolite in bile acids produced in HepG2 cells -a well-differentiated human hepatoblastoma cell line. (PMID 1655725 ).
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB00503 (7a-Hydroxy-3-oxo-5b-cholanoic acid)
C24H38O4
390.5561
390.277009704
(4R)-4-[(1S,2S,7R,9R,10R,11S,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
(4R)-4-[(1S,2S,7R,9R,10R,11S,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
4185-00-6
[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])CC(=O)CC[C@]12C
InChI=1S/C24H38O4/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/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,17?,18+,19+,20-,22+,23+,24-/m1/s1
KNVADAPHVNKTEP-KXIRRPOASA-N
Not classified
Expected but not Quantified
Solid
Not Available
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None
None
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FDB022081
Not Available
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HMDB00503
HMDB00503
5489
53477698
Not Available
Not Available
- Axelson M, Mork B, Everson GT: Bile acid synthesis in cultured human hepatoblastoma cells. J Biol Chem. 1991 Sep 25;266(27):17770-7. [PubMed:1655725 ]
- Goto J, Saisho Y, Nambara T: Studies on steroids. CCLII. Separation and characterization of 3-oxobile acids in serum by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1991 Jul 5;567(2):343-9. [PubMed:1939467 ]
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