MiMeDB: Showing metabocard for Deoxycholic acid (MMDBc0000125)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:36:47 UTC

Update Date

2024-10-07 00:24:39 UTC

Metabolite ID

MMDBc0000125

Metabolite Identification

Common Name

Deoxycholic acid

Description

Deoxycholic acid is a secondary bile acid produced in the liver and is usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends only on the 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 ). When present in sufficiently high levels, deoxycholic acid can act as a hepatotoxin, a metabotoxin, and an oncometabolite. A hepatotoxin causes damage to the liver or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. An oncometabolite is a compound, when present at chronically high levels, that promotes tumour growth and survival. Among the primary bile acids, cholic acid is considered to be the least hepatotoxic while deoxycholic acid is the most hepatoxic (PMID: 1641875 ). The liver toxicity of bile acids appears to be due to their ability to peroxidate lipids and to lyse liver cells. High bile acid levels lead to the generation of reactive oxygen species and reactive nitrogen species, disruption of the cell membrane and mitochondria, induction of DNA damage, mutation and apoptosis, and the development of reduced apoptosis capability upon chronic exposure (PMID: 24884764 ). Chronically high levels of deoxycholic acid are associated with familial hypercholanemia. In hypercholanemia, bile acids, including deoxycholic acid, are elevated in the blood. This disease causes liver damage, extensive itching, poor fat absorption, and can lead to rickets due to lack of calcium in bones. The deficiency of normal bile acids in the intestines results in a deficiency of vitamin K, which also adversely affects clotting of the blood. The bile acid ursodiol (ursodeoxycholic acid) can improve symptoms associated with familial hypercholanemia. Chronically high levels of deoxycholic acid are also associated with several forms of cancer including colon cancer, pancreatic cancer, esophageal cancer, and many other GI cancers.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(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
Deoxycholate	Kegg
3alpha,12alpha-Dihydroxy-5beta-cholanate	Kegg
(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
(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
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	HMDB
Deoxycholic acid, 5alpha isomer	HMDB
Deoxycholic acid, sodium salt, 12beta-isomer	HMDB
Lagodeoxycholic acid	HMDB
Acid, choleic	HMDB
Deoxycholic acid, 12beta isomer	HMDB
Deoxycholic acid, 3beta-isomer	HMDB
Deoxycholic acid, monoammonium salt	HMDB
12beta-Isomer deoxycholic acid	HMDB
3beta-Isomer deoxycholic acid	HMDB
Acid, 5alpha-isomer deoxycholic	HMDB
Acid, deoxycholic	HMDB
Acid, desoxycholic	HMDB
Deoxycholate, sodium	HMDB
Deoxycholic acid, 12beta-isomer	HMDB
Deoxycholic acid, 5alpha-isomer	HMDB
Deoxycholic acid, monopotassium salt	HMDB
Deoxycholic acid, monosodium salt	HMDB
5alpha-Isomer deoxycholic acid	HMDB
Acid, dihydroxycholanoic	HMDB
Choleic acid	HMDB
Deoxycholic acid, 3beta isomer	HMDB
Deoxycholic acid, disodium salt	HMDB
Deoxycholic acid, magnesium (2:1) salt	HMDB
Dihydroxycholanoic acid	HMDB
Sodium deoxycholate	HMDB

Molecular Formula

C₂₄H₄₀O₄

Average Mass

392.572

Monoisotopic Mass

392.292659768

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

83-44-3

SMILES

Not Available

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

InChI Key

KXGVEGMKQFWNSR-LLQZFEROSA-N

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Erythrocyte
Feces
Fibroblasts
Intestine
Urine

Tissue Locations

Erythrocyte
Fibroblasts
Intestine

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192108	Solute carrier organic anion transporter family member 1B3	Transporter	Q9NPD5	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0193395	Canalicular multispecific organic anion transporter 2	Transporter	O15438	Homo sapiens
MMDBp0193400	Bile salt export pump	Transporter	O95342	Homo sapiens
MMDBp0193547	Ileal sodium/bile acid cotransporter	Transporter	Q12908	Homo sapiens
MMDBp0193558	Bile acid receptor	Enzyme	Q96RI1	Homo sapiens
MMDBp0193577	Sodium/bile acid cotransporter	Transporter	Q14973	Homo sapiens
MMDBp0193639	Solute carrier organic anion transporter family member 1A2	Transporter	P46721	Homo sapiens
MMDBp0193865	Solute carrier organic anion transporter family member 4A1	Transporter	Q96BD0	Homo sapiens
MMDBp0195864	Gastrotropin	Unknown	P51161	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0004172	Cholic acid	Deoxycholic acid	Not Available	VMH	11344576 12393855
MMDBr0004173	Cholic acid	Deoxycholic acid	cytochrome P450, family 7, subfamily A, polypeptide 1	VMH	11344576 12393855
MMDBr0004321	Deoxycholic acid	Deoxycholoyl Coenzyme A	Not Available	VMH	6639941
MMDBr0004322	Deoxycholic acid	Deoxycholoyl Coenzyme A	solute carrier family 27 (fatty acid transporter), member 5	VMH	6639941
MMDBr0004323	Lithocholic acid	Deoxycholic acid	Not Available	VMH	11980911
MMDBr0004324	Lithocholic acid	Deoxycholic acid	cytochrome P450, family 8, subfamily B, polypeptide 1	VMH	11980911
MMDBr0009600	Deoxycholic acid	Deoxycholic acid glycine conjugate	Not Available	VMH; KEGG	30371894
MMDBr0012380	Deoxycholic acid	Deoxycholic acid 3-glucuronide	UDP glucuronosyltransferase 2 family, polypeptide A1, complex locus	VMH	30371894
MMDBr0012381	Deoxycholic acid	Deoxycholic acid 3-glucuronide	UDP glucuronosyltransferase 2 family, polypeptide A1, complex locus	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Cystic fibrosis	Slight Increase	Association	Human Blood	HMDB	15185309
Primary biliary cirrhosis		Association	Human Urine	HMDB	2621422

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	23	Human ; Human mucosa; Human feces; Human saliva; Human stool; Human urine; Human sputum	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Bacteroidetes	2	Human feces; Human stool; Human ; Human saliva	Microbial culture
Bacteria	Proteobacteria	1	Human ; Human feces	Microbial culture
Bacteria	Actinobacteria	9	Human ; Human feces; Human saliva; Human mucosa; Human vaginal fluid; Human stool	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Not Available	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.43	0.09			uM	Adult (>18 years old)	Both	Cystic fibrosis	HMDB	15185309
Human Blood	Detected and Quantified	0.76	0.26			uM	Children (1-13 years old)	Both	Cystic fibrosis	HMDB	15185309
Human Urine	Detected and Quantified	0.3		0.06	0.87	umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	0.328		0.0679	0.871	umol/mmol creatinine	Adult (>18 years old)	Both	Primary biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	0.5		0.1	1.3	umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	0.509		0.113	1.324	umol/mmol creatinine	Adult (>18 years old)	Both	Primary biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	0.055		0.05	0.060	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	0.33	0.06			uM	Adult (>18 years old)	Both	Normal	HMDB	15185309
Human Bile	Detected and Quantified	11720		11570	11860	uM	Adult (>18 years old)	Both	Normal	HMDB	16548228
Human Feces	Detected and Quantified	1920.10	1390.50			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Blood	Detected and Quantified	0.57	0.35			uM	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Erythrocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21761941
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	26476344
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000626

DrugBank ID

DB03619

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Deoxycholic acid

METLIN ID

265

PubChem Compound

222528

PDB ID

Not Available

ChEBI ID

28834

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General 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. doi: 10.3109/03009747509165446. [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. doi: 10.1111/j.1365-2362.1978.tb00807.x. [PubMed:417931 ]
Delzenne NM, Calderon PB, Taper HS, Roberfroid MB: Comparative hepatotoxicity of cholic acid, deoxycholic acid and lithocholic acid in the rat: in vivo and in vitro studies. Toxicol Lett. 1992 Jul;61(2-3):291-304. doi: 10.1016/0378-4274(92)90156-e. [PubMed:1641875 ]
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. doi: 10.1172/JCI114050. [PubMed:2708522 ]
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. doi: 10.1016/0304-3835(88)90023-7. [PubMed:3349450 ]
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. doi: 10.1016/0039-128x(86)90029-2. [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 ]
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. doi: 10.1016/0024-3205(83)90643-4. [PubMed:6865641 ]
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 ]
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 ]
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. doi: 10.1242/jeb.204.10.1673. [PubMed:11316487 ]
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. doi: 10.1172/JCI107596. [PubMed:11344576 ]
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 ]
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. doi: 10.1038/sj.ejcn.1601396. [PubMed:12209383 ]
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. doi: 10.1152/ajpgi.00417.2002. [PubMed:12576301 ]
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. doi: 10.1053/j.gastro.2004.05.021. [PubMed:15300575 ]
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. doi: 10.1161/01.ATV.0000178994.21828.a7. Epub 2005 Jul 21. [PubMed:16037564 ]
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 ]
Duret G, Delcour AH: Deoxycholic acid blocks vibrio cholerae OmpT but not OmpU porin. J Biol Chem. 2006 Jul 21;281(29):19899-905. doi: 10.1074/jbc.M602426200. Epub 2006 May 2. [PubMed:16670088 ]
Ajouz H, Mukherji D, Shamseddine A: Secondary bile acids: an underrecognized cause of colon cancer. World J Surg Oncol. 2014 May 24;12:164. doi: 10.1186/1477-7819-12-164. [PubMed:24884764 ]

Showing metabocard for Deoxycholic acid (MMDBc0000125)

MOL for #<Metabolite:0x00007fdb361c5ac0>

3D MOL for #<Metabolite:0x00007fdb361c5ac0>

3D SDF for #<Metabolite:0x00007fdb361c5ac0>

3D-SDF for #<Metabolite:0x00007fdb361c5ac0>

PDB for #<Metabolite:0x00007fdb361c5ac0>

3D PDB for #<Metabolite:0x00007fdb361c5ac0>

SMILES for #<Metabolite:0x00007fdb361c5ac0>

INCHI for #<Metabolite:0x00007fdb361c5ac0>

Structure for #<Metabolite:0x00007fdb361c5ac0>

3D Structure for #<Metabolite:0x00007fdb361c5ac0>