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Showing Compound Deoxycholic acid (FDB012780)

Record Information
Version1.0
Creation date2010-04-08 22:10:21 UTC
Update date2015-10-09 22:27:46 UTC
Primary IDFDB012780
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDeoxycholic acid
DescriptionEmulsifying agent used in foods 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); Deoxycholic acid, also known as deoxycholate, cholanoic acid, and 3?,12?-dihydroxy-5?-cholanate, is a bile acid. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The two primary bile acids secreted by the liver are cholic acid and chenodeoxycholic acid. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid lithocholic acid, and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as ursodeoxycholic acid. Deoxycholic acid is soluble in alcohol and acetic acid. When pure, it comes in a white to off-white crystalline powder form.; In China, the traditional medicine "Niuhuang", which in Chinese means "Oxen Yellow" and is actually bilestone of oxen, has been in use for two millennia for the treatment of inflammation as well as to enhance the immune system. One of its main components is DCA.
CAS Number83-44-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3a,12b-Dihydroxy-5a-cholan-24-OateGenerator
3a,12b-Dihydroxy-5a-cholan-24-Oic acidGenerator
3alpha,12beta-Dihydroxy-5alpha-cholan-24-OateGenerator
3Α,12β-dihydroxy-5α-cholan-24-OateGenerator
3Α,12β-dihydroxy-5α-cholan-24-Oic acidGenerator
DeoxycholateHMDB
(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-OateGenerator
(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oic acidGenerator
(3a,5b,12a)-3,12-Dihydroxycholan-24-OateGenerator
(3a,5b,12a)-3,12-Dihydroxycholan-24-Oic acidGenerator
(3alpha,5alpha,12alpha)-3,12-DIHYDROXYCHOLAN-24-OateGenerator
(3ALPHA,5ALPHA,12ALPHA)-3,12-DIHYDROXYCHOLAN-24-OIC ACIDChEBI
(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-OateGenerator
(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acidChEBI
(3α,5α,12α)-3,12-dihydroxycholan-24-OateGenerator
(3α,5α,12α)-3,12-dihydroxycholan-24-Oic acidGenerator
(3α,5β,12α)-3,12-dihydroxycholan-24-OateGenerator
(3α,5β,12α)-3,12-dihydroxycholan-24-Oic acidGenerator
17α, 12α-diolbiospider
3,12-Dihydroxycholanic acidbiospider
3a,12a-Dihydroxy-5b-cholanateGenerator
3a,12a-Dihydroxy-5b-cholanic acidGenerator
3alpha,12alpha-Dihydroxy-5beta-cholanatebiospider
3alpha,12alpha-Dihydroxy-5beta-cholanic acidbiospider
3α,12α-dihydroxy-5β-cholanateGenerator
3α,12α-dihydroxy-5β-cholanic acidGenerator
5α,12α-dihydroxy-biospider
5b-Cholanic acid-3a,12a-diolbiospider
5b-Deoxycholatebiospider
5b-Deoxycholic acidbiospider
7-Deoxycholatebiospider
7-Deoxycholic acidbiospider
7α-Deoxycholic acidbiospider
7a-DeoxycholateGenerator
7a-Deoxycholic acidGenerator
7alpha-DeoxycholateGenerator
7alpha-Deoxycholic acidChEBI
7α-deoxycholateGenerator
7α-deoxycholic acidGenerator
Cholan-24-oic acid, 3,12-dihydroxy-, (3α,5α)-biospider
Choleic aciddb_source
Cholerebicbiospider
Cholic acid, deoxy-biospider
Cholorebicbiospider
Cholorebic aciddb_source
Degalolbiospider
Deoxy-cholatebiospider
Deoxy-cholic acidbiospider
Deoxycholatatebiospider
Deoxycholatic acidbiospider
Deoxycholic aciddb_source
DesoxycholateGenerator
Desoxycholic acidbiospider
DesoxycholsaeureChEBI
Droxolandb_source
Pyrocholdb_source
Septocholdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP3.3ALOGPS
logP3.79ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-0.35ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.2 m³·mol⁻¹ChemAxon
Polarizability46.55 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H40O4
IUPAC name4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoic acid
InChI IdentifierInChI=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)
InChI KeyKXGVEGMKQFWNSR-UHFFFAOYSA-N
Isomeric SMILESCC(CCC(O)=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C
Average Molecular Weight392.572
Monoisotopic Molecular Weight392.292659768
Classification
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-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 FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 73.43%; H 10.27%; O 16.30%DFC
Melting PointMp 187-189°DFC
Boiling PointNot Available
Experimental Water Solubility0.0436 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP3.50RODA,A ET AL. (1990)
Experimental pKa6.58 1
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +53 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDeoxycholic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ta-0119000000-c9b70e50e3c7d399a348Spectrum
Predicted GC-MSDeoxycholic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxycholic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0019000000-29dd7a61f282d9750e032021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abc-3159000000-8e9dbfb4a0337649d1b22021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9740000000-11f4e5997fe2172f813a2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-7eba834115ee2c6792082021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-93035c7b2c4fda529f062021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1049000000-e25f8794872bcca4fb182021-10-12View Spectrum
NMRNot Available
ChemSpider ID193196
ChEMBL IDCHEMBL406393
KEGG Compound IDC04483
Pubchem Compound ID222528
Pubchem Substance IDNot Available
ChEBI ID28834
Phenol-Explorer IDNot Available
DrugBank IDDB03619
HMDB IDHMDB00626
CRC / DFC (Dictionary of Food Compounds) IDHHS99-P:HKW65-R
EAFUS ID867
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00030117
HET IDDXC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDeoxycholic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Bile acid receptorNR1H4Q96RI1
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference