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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:41 -0600
Update Date	2015-09-13 15:15:32 -0600
Secondary Accession Numbers	ECMDB21387
Identification
Name:	Deoxycholic acid
Description	Deoxycholic 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.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb1da2378> Close
Synonyms:	3α,12α-dihydroxy-5β-cholanate 3α,12α-dihydroxy-5β-cholanic acid 3a,12a-Dihydroxy-5b-cholanate 3a,12a-Dihydroxy-5b-cholanic acid 3alpha,12alpha-dihydroxy-5beta-cholanate 3alpha,12alpha-dihydroxy-5beta-cholanic acid 3α,12α-Dihydroxy-5β-cholanate 3α,12α-Dihydroxy-5β-cholanic acid 5b-Cholanate-3a,12a-diol 5b-Cholanic acid-3a,12a-diol 5b-Deoxycholate 5b-Deoxycholic acid 7-Deoxycholate 7-Deoxycholic acid Cholerebic Cholorebic Degalol Deoxy-Cholate Deoxy-Cholic acid Deoxycholatate Deoxycholate Deoxycholatic acid Deoxycholic acid
Chemical Formula:	C24H40O4
Weight:	Average: 392.572 Monoisotopic: 392.292659768
InChI Key:	KXGVEGMKQFWNSR-LLQZFEROSA-N
InChI:	InChI=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/s1
CAS number:	83-44-3
IUPAC Name:	(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
Traditional IUPAC Name:	(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
SMILES:	[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@]12C
Chemical Taxonomy
Description	belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Steroids and steroid derivatives
Sub Class	Bile acids, alcohols and derivatives
Direct Parent	Dihydroxy bile acids, alcohols and derivatives
Alternative Parents	3-alpha-hydroxysteroids 12-hydroxysteroids Secondary alcohols Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Dihydroxy bile acid, alcohol, or derivatives 3-hydroxysteroid 3-alpha-hydroxysteroid 12-hydroxysteroid Hydroxysteroid Cyclic alcohol Secondary alcohol Carboxylic acid Carboxylic acid derivative Monocarboxylic acid or derivatives Organooxygen compound Organic oxygen compound Hydrocarbon derivative Organic oxide Carbonyl group Alcohol Aliphatic homopolycyclic compound
Molecular Framework	Aliphatic homopolycyclic compounds
External Descriptors	bile acid (CHEBI:28834 ) dihydroxy-5beta-cholanic acid (CHEBI:28834 ) C24 bile acids, alcohols, and derivatives (C04483 ) Cholane and derivatives (C04483 ) C24 bile acids, alcohols, and derivatives (LMST04010040 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	171-174 °C
Experimental Properties:	Property Value Source Water Solubility: 0.0436 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] PhysProp LogP: 3.50 [RODA,A ET AL. (1990)] PhysProp
Predicted Properties	Property Value Source Water Solubility 0.017 g/L ALOGPS logP 3.3 ALOGPS logP 3.79 ChemAxon logS -4.3 ALOGPS pKa (Strongest Acidic) 4.65 ChemAxon pKa (Strongest Basic) -0.35 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 77.76 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 109.2 m³·mol⁻¹ ChemAxon Polarizability 46.3 ų ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:
SMPDB Pathways:	inner membrane transport PW000786
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-00os-0119000000-ff101495d4bc6a37fc83 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-0006-1110390000-cc7d539ad02f4039ec09 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) splash10-0006-0009000000-8b9c4803e9cb1d194c2e View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) splash10-0006-0009000000-cccabd9d13ac783b6e31 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) splash10-0007-2009000000-d7c20760d2074c07af22 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-0006-0009000000-269a5d1ed75b71c78ecb View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative splash10-0007-0009000000-72f1acf9f31f344daaa1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative splash10-000x-0008000900-ebb0e6a61bd8f06a21f7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-IT , negative splash10-0002-0009000000-8078ef73008efc65c713 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-0006-0009000000-269a5d1ed75b71c78ecb View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-0007-0009000000-827a9ce119d7f2f1cb5c View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-0006-0009000000-ade8ee412cabab0a5cdd View in MoNA LC-MS/MS LC-MS/MS Spectrum - 30V, Negative splash10-0007-0009000000-827a9ce119d7f2f1cb5c View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-0006-0009000000-46347f9ccba012a193b3 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-0007-0009000000-7de3b9549dc580acb2af View in MoNA LC-MS/MS LC-MS/MS Spectrum - 30V, Positive splash10-0007-0009000000-72f1acf9f31f344daaa1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-0007-0009000000-fa7c4f74eaf1bb2e1f57 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-0006-0009000000-737c78b82fef7180b7ac View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-0006-0009000000-eb86d43bab0334d7cfe4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-056r-0009000000-db8bf3905980e8620f12 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-056r-0009000000-6a632f1c8fbb19a314cb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014i-4219000000-29a9a2c5d3d148fca202 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0006-0009000000-ab9ac299290313e78fe4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-006x-1009000000-6444232cac6b7a24dd96 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9006000000-b2f4c82d34550211259c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-054o-0019000000-a4dfbb4ad2f96e8ee6db View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0adl-4298000000-b6171657518bf9639cbe View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Andersen 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. Pubmed: 52191 Beher 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. Pubmed: 6865641 Berr 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. Pubmed: 2708522 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 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 Costarelli 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. Pubmed: 12209383 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 Deleze 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. Pubmed: 417931 Duret 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. Pubmed: 16670088 Heikkinen 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. Pubmed: 7383489 Nobuoka 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. Pubmed: 15300575 Rudi J, Schonig T, Stremmel W: -Therapy with ursodeoxycholic acid in primary biliary cirrhosis in pregnancy-. Z Gastroenterol. 1996 Mar;34(3):188-91. Pubmed: 8650973 Salen 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. Pubmed: 11344576 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 Stadler 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. Pubmed: 3349450 Stellard 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. Pubmed: 3559388 Tadano 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. Pubmed: 16548228 Yamaga 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. Pubmed: 3445292
Synthesis Reference:	He, Zhiquan. in-situ generation of deoxycholic acid by poultry for Chinese medicine. Faming Zhuanli Shenqing Gongkai Shuomingshu (1993), 3 pp.
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 23614 HMDB ID HMDB00626 Pubchem Compound ID 440355 Kegg ID C04483 ChemSpider ID 193196 Wikipedia Deoxycholic acid BioCyc ID DEOXYCHOLATE EcoCyc ID DEOXYCHOLATE Ligand Expo DXC

Transporters