2.02012-07-30 14:55:41 -06002015-09-13 15:15:32 -0600ECMDB21387M2MDB001782Deoxycholic acidDeoxycholic acid is 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. 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.
3α,12α-dihydroxy-5β-cholanate3α,12α-dihydroxy-5β-cholanic acid3a,12a-Dihydroxy-5b-cholanate3a,12a-Dihydroxy-5b-cholanic acid3alpha,12alpha-dihydroxy-5beta-cholanate3alpha,12alpha-dihydroxy-5beta-cholanic acid3α,12α-Dihydroxy-5β-cholanate3α,12α-Dihydroxy-5β-cholanic acid5b-Cholanate-3a,12a-diol5b-Cholanic acid-3a,12a-diol5b-Deoxycholate5b-Deoxycholic acid7-Deoxycholate7-Deoxycholic acidCholerebicCholorebicDegalolDeoxy-CholateDeoxy-Cholic acidDeoxycholatateDeoxycholateDeoxycholatic acidDeoxycholic acidC24H40O4392.572392.292659768(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid83-44-3[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12CInChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1KXGVEGMKQFWNSR-LLQZFEROSA-NSolidMembranelogp3.30logs-4.35solubility1.73e-02 g/lmelting_point171-174 oClogp3.79pka_strongest_acidic4.65pka_strongest_basic-0.35iupac(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acidaverage_mass392.572mono_mass392.292659768smiles[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12CformulaC24H40O4inchiInChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1inchikeyKXGVEGMKQFWNSR-LLQZFEROSA-Npolar_surface_area77.76refractivity109.2polarizability46.3rotatable_bond_count4acceptor_count4donor_count3physiological_charge-1formal_charge0inner membrane transportlist of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol
This pathway should be updated regularly with the new inner membrae transports addedPW000786MetabolicSpecdb::CMs9656Specdb::CMs37659Specdb::CMs134152Specdb::CMs141886Specdb::CMs1070675Specdb::CMs1070677Specdb::CMs1070679Specdb::CMs1070681Specdb::CMs1070683Specdb::CMs1070685Specdb::CMs1070687Specdb::CMs1070689Specdb::CMs1070691Specdb::CMs1070693Specdb::CMs1070695Specdb::CMs1070697Specdb::CMs1070699Specdb::NmrOneD1443Specdb::MsMs852Specdb::MsMs853Specdb::MsMs854Specdb::MsMs4243Specdb::MsMs4244Specdb::MsMs4245Specdb::MsMs248661Specdb::MsMs248662Specdb::MsMs248663Specdb::MsMs268602Specdb::MsMs268603Specdb::MsMs268604Specdb::MsMs438694Specdb::MsMs439280Specdb::MsMs439281Specdb::MsMs2244215Specdb::MsMs2245898Specdb::MsMs2246363Specdb::MsMs2247903Specdb::MsMs2248356Specdb::MsMs2250038Specdb::MsMs2250327Specdb::MsMs2252047Specdb::MsMs2672001Specdb::MsMs2672002Specdb::NmrTwoD1388HMDB00626440355193196C0448323614DEOXYCHOLATEDXCDeoxycholic acidTadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10.16548228Salen G, Tint GS, Eliav B, Deering N, Mosbach EH: Increased formation of ursodeoxycholic acid in patients treated with chenodeoxycholic acid. J Clin Invest. 1974 Feb;53(2):612-21.11344576Berr F, Stellaard F, Pratschke E, Paumgartner G: Effects of cholecystectomy on the kinetics of primary and secondary bile acids. J Clin Invest. 1989 May;83(5):1541-50.2708522Yamaga N, Adachi K, Shimizu K, Miyake S, Sumi F, Miyagawa I, Goto H: Bile acids of patients with renal failure receiving chronic hemodialysis. Steroids. 1986 Nov-Dec;48(5-6):427-38.3445292Stellard F, Paumgartner G, van Berge Henegouwen GP, van der Werf SD: Determination of deoxycholic acid pool size and input rate using [24-13C]deoxycholic acid and serum sampling. J Lipid Res. 1986 Nov;27(11):1222-5.3559388Andersen RB, Bruusgaard A: Effect of the common bile acids on the fibrin/fibrinogen fragments in rheumatoid synovial fluid. A possible clue to the ameliorating effect of jaundice in rheumatoid arthritis. Scand J Rheumatol. 1975;4(3):158-64.52191Deleze G, Paumgartner G, Karlaganis G, Giger W, Reinhard M, Sidiropoulos D: Bile acid pattern in human amniotic fluid. Eur J Clin Invest. 1978 Feb;8(1):41-5.417931Beher WT, Gabbard A, Norum RA, Stradnieks S: Effect of blood high density lipoprotein cholesterol concentration on fecal steroid excretion in humans. Life Sci. 1983 Jun 27;32(26):2933-7.6865641Nobuoka A, Takayama T, Miyanishi K, Sato T, Takanashi K, Hayashi T, Kukitsu T, Sato Y, Takahashi M, Okamoto T, Matsunaga T, Kato J, Oda M, Azuma T, Niitsu Y: Glutathione-S-transferase P1-1 protects aberrant crypt foci from apoptosis induced by deoxycholic acid. Gastroenterology. 2004 Aug;127(2):428-43.15300575Rudi J, Schonig T, Stremmel W: -Therapy with ursodeoxycholic acid in primary biliary cirrhosis in pregnancy-. Z Gastroenterol. 1996 Mar;34(3):188-91.8650973Heikkinen J, Maentausta O, Tuimala R, Ylostalo P, Janne O: Amniotic fluid bile acids in normal and pathologic pregnancy. Obstet Gynecol. 1980 Jul;56(1):60-4.7383489Duret G, Delcour AH: Deoxycholic acid blocks vibrio cholerae OmpT but not OmpU porin. J Biol Chem. 2006 Jul 21;281(29):19899-905. Epub 2006 May 2.16670088Costarelli V, Sanders TA: Plasma deoxycholic acid concentration is elevated in postmenopausal women with newly diagnosed breast cancer. Eur J Clin Nutr. 2002 Sep;56(9):925-7.12209383Stadler J, Yeung KS, Furrer R, Marcon N, Himal HS, Bruce WR: Proliferative activity of rectal mucosa and soluble fecal bile acids in patients with normal colons and in patients with colonic polyps or cancer. Cancer Lett. 1988 Jan;38(3):315-20.3349450St-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):1673-86.11316487Claudel 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 21.16037564Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56.12576301Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43.11907135He, Zhiquan. in-situ generation of deoxycholic acid by poultry for Chinese medicine. Faming Zhuanli Shenqing Gongkai Shuomingshu (1993), 3 pp.http://hmdb.ca/system/metabolites/msds/000/000/545/original/HMDB00626.pdf?1358894069Multidrug resistance protein mdtKP37340MDTK_ECOLImdtKhttp://ecmdb.ca/proteins/P37340.xmlMultidrug resistance protein mdtAP76397MDTA_ECOLImdtAhttp://ecmdb.ca/proteins/P76397.xmlMultidrug resistance protein mdtBP76398MDTB_ECOLImdtBhttp://ecmdb.ca/proteins/P76398.xmlMultidrug resistance protein mdtCP76399MDTC_ECOLImdtChttp://ecmdb.ca/proteins/P76399.xml