Livestock Metabolome Database: Showing metabocard for Deoxycholic acid (LMDB00195)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:44:26 UTC

Update Date

2018-04-30 21:14:38 UTC

Lmdb

LMDB00195

Secondary Accession Numbers

None

Metabolite Identification

Common 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. 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 ).

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

Chemical Formula

C₂₄H₄₀O₄

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

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 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

CAS Registry Number

83-44-3

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O

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 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.2 m³·mol⁻¹	ChemAxon
Polarizability	46.3 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00os-0119000000-ff101495d4bc6a37fc83	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-1110390000-cc7d539ad02f4039ec09	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0006-0009000000-8b9c4803e9cb1d194c2e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-0009000000-cccabd9d13ac783b6e31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0007-2009000000-d7c20760d2074c07af22	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0006-0009000000-269a5d1ed75b71c78ecb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0007-0009000000-72f1acf9f31f344daaa1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-000x-0008000900-ebb0e6a61bd8f06a21f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0002-0009000000-8078ef73008efc65c713	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0009000000-269a5d1ed75b71c78ecb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0007-0009000000-827a9ce119d7f2f1cb5c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-ade8ee412cabab0a5cdd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0007-0009000000-827a9ce119d7f2f1cb5c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-46347f9ccba012a193b3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0007-0009000000-7de3b9549dc580acb2af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0007-0009000000-72f1acf9f31f344daaa1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0007-0009000000-fa7c4f74eaf1bb2e1f57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-737c78b82fef7180b7ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-eb86d43bab0334d7cfe4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0009000000-db8bf3905980e8620f12	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0009000000-6a632f1c8fbb19a314cb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-4219000000-29a9a2c5d3d148fca202	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-ab9ac299290313e78fe4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-1009000000-6444232cac6b7a24dd96	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-b2f4c82d34550211259c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-054o-0019000000-a4dfbb4ad2f96e8ee6db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0adl-4298000000-b6171657518bf9639cbe	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Bile acid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Bile acid	Detected but not Quantified	Not Applicable	Not Available	Porcine	21859467	details

External Links

DrugBank ID

DB03619

HMDB ID

HMDB0000626

FooDB ID

FDB012780

Phenol Explorer ID

Not Available

KNApSAcK ID

C00030117

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

265

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB21387

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [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. [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. [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. [11907135 ]

Showing metabocard for Deoxycholic acid (LMDB00195)

Structure for LMDB00195 (Deoxycholic acid)