| Record Information |
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| Version | 3.6 |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2017-03-02 21:26:01 UTC |
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| HMDB ID | HMDB00626 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | Deoxycholic acid |
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| 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. 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 molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate 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 accumulation in blood and tissues. (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| (3ALPHA,5ALPHA,12ALPHA)-3,12-DIHYDROXYCHOLAN-24-OIC ACID | ChEBI | | (3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acid | ChEBI | | 3alpha,12alpha-Dihydroxy-5beta-cholanic acid | ChEBI | | 7alpha-Deoxycholic acid | ChEBI | | Desoxycholic acid | ChEBI | | Desoxycholsaeure | ChEBI | | (3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oate | Generator | | (3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oic acid | Generator | | (3alpha,5alpha,12alpha)-3,12-DIHYDROXYCHOLAN-24-Oate | Generator | | (3α,5α,12α)-3,12-dihydroxycholan-24-Oate | Generator | | (3α,5α,12α)-3,12-dihydroxycholan-24-Oic acid | Generator | | Deoxycholate | Generator | | (3a,5b,12a)-3,12-Dihydroxycholan-24-Oate | Generator | | (3a,5b,12a)-3,12-Dihydroxycholan-24-Oic acid | Generator | | (3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oate | Generator | | (3α,5β,12α)-3,12-dihydroxycholan-24-Oate | Generator | | (3α,5β,12α)-3,12-dihydroxycholan-24-Oic acid | Generator | | 3a,12a-Dihydroxy-5b-cholanate | Generator | | 3a,12a-Dihydroxy-5b-cholanic acid | Generator | | 3alpha,12alpha-Dihydroxy-5beta-cholanate | Generator | | 3α,12α-dihydroxy-5β-cholanate | Generator | | 3α,12α-dihydroxy-5β-cholanic acid | Generator | | 7a-Deoxycholate | Generator | | 7a-Deoxycholic acid | Generator | | 7alpha-Deoxycholate | Generator | | 7α-deoxycholate | Generator | | 7α-deoxycholic acid | Generator | | Desoxycholate | Generator | | 5b-Cholanic acid-3a,12a-diol | HMDB | | 5b-Deoxycholate | HMDB | | 5b-Deoxycholic acid | HMDB | | 7-Deoxycholate | HMDB | | 7-Deoxycholic acid | HMDB | | Cholerebic | HMDB | | Cholorebic | HMDB | | Degalol | HMDB | | Deoxy-cholate | HMDB | | Deoxy-cholic acid | HMDB | | Deoxycholatate | HMDB | | Deoxycholatic acid | HMDB | | Acid, lagodeoxycholic | MeSH | | Deoxycholic acid, 5alpha isomer | MeSH | | Deoxycholic acid, sodium salt, 12beta-isomer | MeSH | | Lagodeoxycholic acid | MeSH | | Acid, choleic | MeSH | | Deoxycholic acid, 12beta isomer | MeSH | | Deoxycholic acid, 3beta-isomer | MeSH | | Deoxycholic acid, monoammonium salt | MeSH | | 12beta-Isomer deoxycholic acid | MeSH | | 3beta-Isomer deoxycholic acid | MeSH | | Acid, 5alpha-isomer deoxycholic | MeSH | | Acid, deoxycholic | MeSH | | Acid, desoxycholic | MeSH | | Deoxycholate, sodium | MeSH | | Deoxycholic acid, 12beta-isomer | MeSH | | Deoxycholic acid, 5alpha-isomer | MeSH | | Deoxycholic acid, monopotassium salt | MeSH | | Deoxycholic acid, monosodium salt | MeSH | | 5alpha-Isomer deoxycholic acid | MeSH | | Acid, dihydroxycholanoic | MeSH | | Choleic acid | MeSH | | Deoxycholic acid, 3beta isomer | MeSH | | Deoxycholic acid, disodium salt | MeSH | | Deoxycholic acid, magnesium (2:1) salt | MeSH | | Dihydroxycholanoic acid | MeSH | | Sodium deoxycholate | MeSH |
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| Chemical Formula | C24H40O4 |
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| Average Molecular Weight | 392.572 |
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| Monoisotopic Molecular Weight | 392.292659768 |
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| IUPAC Name | (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid |
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| Traditional Name | deoxycholic acid |
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| CAS Registry Number | 83-44-3 |
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| 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 |
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| InChI Identifier | 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 |
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| InChI Key | KXGVEGMKQFWNSR-LLQZFEROSA-N |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Bile acids, alcohols and derivatives |
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| Direct Parent | Dihydroxy bile acids, alcohols and derivatives |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | - Cell signaling
- Fat solubilization and Waste products
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application | - Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 171 - 174 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.0436 mg/mL | Not Available | | LogP | 3.50 | RODA,A ET AL. (1990) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0006-0009000000-8b9c4803e9cb1d194c2e | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0006-0009000000-cccabd9d13ac783b6e31 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0007-2009000000-d7c20760d2074c07af22 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0006-0009000000-269a5d1ed75b71c78ecb | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative | splash10-0007-0009000000-72f1acf9f31f344daaa1 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative | splash10-000x-0008000900-ebb0e6a61bd8f06a21f7 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0002-0009000000-8078ef73008efc65c713 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0007-0009000000-827a9ce119d7f2f1cb5c | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0002-0009000000-cd16299b1619dba84811 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0002-0009000000-49b6bd17b06a31996509 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0002-0009000000-ede681f2d634d5fa5c78 | View in MoNA |
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| 1D NMR | 1H NMR Spectrum | Not Available |
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| 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
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| General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- Stellaard 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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