Identification

Name
Deoxycholic Acid
Accession Number
DB03619  (EXPT01194, DB07690)
Type
Small Molecule
Groups
Approved
Description

Deoxycholic acid is a a bile acid which emulsifies and solubilizes dietary fats in the intestine, and when injected subcutaneously, it disrupts cell membranes in adipocytes and destroys fat cells in that tissue. In April 2015, deoxycholic acid was approved by the FDA for the treatment submental fat to improve aesthetic appearance and reduce facial fullness or convexity. It is marketed under the brand name Kybella by Kythera Biopharma and is the first pharmacological agent available for submental fat reduction, allowing for a safer and less invasive alternative than surgical procedures.

Structure
Thumb
Synonyms
  • (3α,5β,12α)-3,12-dihydroxycholan-24-oic acid
  • 3alpha,12alpha-Dihydroxy-5beta-cholanic acid
  • 7α-deoxycholic acid
  • deoxycholate
  • desoxycholic acid
  • Desoxycholsäure
External IDs
ATX-101
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BelkyraSolution10 mgSubcutaneousKythera Biopharmaceuticals2016-01-27Not applicableCanada
KybellaInjection, solution20 mg/2mLSubcutaneousKythera Biopharmaceuticals2015-05-18Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
DebilineDeoxycholic Acid (100 mg) + Pepsin (50 mg)TabletOralLab Nadeau LtÉe, Division Of Technilab Inc.1951-12-311999-09-28Canada
Debiline HDeoxycholic Acid (100 mg) + Homatropine Methylbromide (2.5 mg) + Pepsin (50 mg)TabletOralLab Nadeau LtÉe, Division Of Technilab Inc.1951-12-311999-09-28Canada
Categories
UNII
005990WHZZ
CAS number
83-44-3
Weight
Average: 392.572
Monoisotopic: 392.292659768
Chemical Formula
C24H40O4
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
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
SMILES

Pharmacology

Indication

For improvement in appearance of moderate to severe fullness associated with submental fat in adults.

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action

As a bile acid, deoxycholic acid emulsifies fat in the gut. Synthetically derived deoxycholic acid, when injected, stimulates a targeted breakdown of adipose cells by disrupting the cell membrane and causing adipocytolysis. This results in an inflammatory reaction and clearing of the adipose tissue remnants by macrophages. Deoxycholic acid's actions are reduced by albumin and tissue-associated proteins, therefore its effect is limited to protein-poor subcutaneous fat tissue. Protein-rich tissues like muscle and skin are unaffected by deoxycholic acid, contributing to its safety profile.

TargetActionsOrganism
USteroid Delta-isomeraseNot AvailablePseudomonas putida
UPpcANot AvailableGeobacter sulfurreducens
UElongation factor Tu GTP-binding domain-containing protein 1Not AvailableHuman
UCholoylglycine hydrolaseNot AvailableClostridium perfringens (strain 13 / Type A)
ULactaldehyde dehydrogenaseNot AvailableEscherichia coli (strain K12)
UAcriflavine resistance protein BNot AvailableEscherichia coli (strain K12)
UCytochrome c oxidase subunit 1Not AvailableRhodobacter sphaeroides
UCytochrome c oxidase subunit 2Not AvailableRhodobacter sphaeroides
UBile acid receptorNot AvailableHuman
UGlutathione S-transferase PNot AvailableHuman
UG-protein coupled bile acid receptor 1Not AvailableHuman
Absorption

Deoxycholic acid is rapidly absorbed after subcutaneous administration. After maximum recommended single treatment dose, 100mg, the post-treatment plasma levels returned to endogenous levels within 24 hours. With the proposed treatment guideline, no accumulation is expected.

Volume of distribution
Not Available
Protein binding

98%

Metabolism

Deoxycholic acid is not metabolized to any significant extent under normal conditions.

Route of elimination

The exogenous deoxycholic acid joins the endogenous bile acid pool in the enterohepatic circulation and is excreted unchanged in feces along with endogenous deoxycholic acid.

Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbciximabThe risk or severity of adverse effects can be increased when Abciximab is combined with Deoxycholic Acid.Approved
AcenocoumarolThe risk or severity of adverse effects can be increased when Acenocoumarol is combined with Deoxycholic Acid.Approved
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Deoxycholic Acid.Approved, Vet Approved
AlprostadilThe risk or severity of adverse effects can be increased when Alprostadil is combined with Deoxycholic Acid.Approved, Investigational
AnagrelideThe risk or severity of adverse effects can be increased when Anagrelide is combined with Deoxycholic Acid.Approved
AncrodThe risk or severity of adverse effects can be increased when Ancrod is combined with Deoxycholic Acid.Investigational
AndrographolideThe risk or severity of adverse effects can be increased when Andrographolide is combined with Deoxycholic Acid.Investigational
Antithrombin III humanThe risk or severity of adverse effects can be increased when Antithrombin III human is combined with Deoxycholic Acid.Approved
ApixabanThe risk or severity of adverse effects can be increased when Apixaban is combined with Deoxycholic Acid.Approved
ArdeparinThe risk or severity of adverse effects can be increased when Ardeparin is combined with Deoxycholic Acid.Approved, Investigational, Withdrawn
ArgatrobanThe risk or severity of adverse effects can be increased when Argatroban is combined with Deoxycholic Acid.Approved, Investigational
AzelastineThe risk or severity of adverse effects can be increased when Azelastine is combined with Deoxycholic Acid.Approved
BecaplerminThe risk or severity of adverse effects can be increased when Becaplermin is combined with Deoxycholic Acid.Approved, Investigational
BeraprostThe risk or severity of adverse effects can be increased when Beraprost is combined with Deoxycholic Acid.Investigational
BivalirudinThe risk or severity of adverse effects can be increased when Bivalirudin is combined with Deoxycholic Acid.Approved, Investigational
BuflomedilThe risk or severity of adverse effects can be increased when Buflomedil is combined with Deoxycholic Acid.Experimental
ButylphthalideThe risk or severity of adverse effects can be increased when Butylphthalide is combined with Deoxycholic Acid.Investigational
CangrelorThe risk or severity of adverse effects can be increased when Cangrelor is combined with Deoxycholic Acid.Approved
CertoparinThe risk or severity of adverse effects can be increased when Certoparin is combined with Deoxycholic Acid.Approved, Investigational
CilostazolThe risk or severity of adverse effects can be increased when Cilostazol is combined with Deoxycholic Acid.Approved
Citric AcidThe risk or severity of adverse effects can be increased when Citric Acid is combined with Deoxycholic Acid.Approved, Nutraceutical, Vet Approved
ClopidogrelThe risk or severity of adverse effects can be increased when Clopidogrel is combined with Deoxycholic Acid.Approved, Nutraceutical
CloricromenThe risk or severity of adverse effects can be increased when Cloricromen is combined with Deoxycholic Acid.Experimental
Dabigatran etexilateThe risk or severity of adverse effects can be increased when Dabigatran etexilate is combined with Deoxycholic Acid.Approved
DalteparinThe risk or severity of adverse effects can be increased when Dalteparin is combined with Deoxycholic Acid.Approved
DanaparoidThe risk or severity of adverse effects can be increased when Danaparoid is combined with Deoxycholic Acid.Approved, Withdrawn
DarexabanThe risk or severity of adverse effects can be increased when Darexaban is combined with Deoxycholic Acid.Investigational
DefibrotideThe risk or severity of adverse effects can be increased when Defibrotide is combined with Deoxycholic Acid.Approved, Investigational
DesirudinThe risk or severity of adverse effects can be increased when Desirudin is combined with Deoxycholic Acid.Approved
DextranThe risk or severity of adverse effects can be increased when Dextran is combined with Deoxycholic Acid.Approved, Vet Approved
Dextran 40The risk or severity of adverse effects can be increased when Dextran 40 is combined with Deoxycholic Acid.Approved
Dextran 70The risk or severity of adverse effects can be increased when Dextran 70 is combined with Deoxycholic Acid.Approved
Dextran 75The risk or severity of adverse effects can be increased when Dextran 75 is combined with Deoxycholic Acid.Approved
DicoumarolThe risk or severity of adverse effects can be increased when Dicoumarol is combined with Deoxycholic Acid.Approved
DipyridamoleThe risk or severity of adverse effects can be increased when Dipyridamole is combined with Deoxycholic Acid.Approved
Edetic AcidThe risk or severity of adverse effects can be increased when Edetic Acid is combined with Deoxycholic Acid.Approved, Vet Approved
EdoxabanThe risk or severity of adverse effects can be increased when Edoxaban is combined with Deoxycholic Acid.Approved
EnoxaparinThe risk or severity of adverse effects can be increased when Enoxaparin is combined with Deoxycholic Acid.Approved
EpinastineThe risk or severity of adverse effects can be increased when Epinastine is combined with Deoxycholic Acid.Approved, Investigational
EplivanserinThe risk or severity of adverse effects can be increased when Eplivanserin is combined with Deoxycholic Acid.Investigational
eplivanserineThe risk or severity of adverse effects can be increased when eplivanserine is combined with Deoxycholic Acid.Investigational
EpoprostenolThe risk or severity of adverse effects can be increased when Epoprostenol is combined with Deoxycholic Acid.Approved
EptifibatideThe risk or severity of adverse effects can be increased when Eptifibatide is combined with Deoxycholic Acid.Approved, Investigational
Ethyl biscoumacetateThe risk or severity of adverse effects can be increased when Ethyl biscoumacetate is combined with Deoxycholic Acid.Withdrawn
Ferulic acidThe risk or severity of adverse effects can be increased when Ferulic acid is combined with Deoxycholic Acid.Experimental
FluindioneThe risk or severity of adverse effects can be increased when Fluindione is combined with Deoxycholic Acid.Investigational
FondaparinuxThe risk or severity of adverse effects can be increased when Fondaparinux is combined with Deoxycholic Acid.Investigational
Fondaparinux sodiumThe risk or severity of adverse effects can be increased when Fondaparinux sodium is combined with Deoxycholic Acid.Approved, Investigational
GabexateThe risk or severity of adverse effects can be increased when Gabexate is combined with Deoxycholic Acid.Investigational
HeparinThe risk or severity of adverse effects can be increased when Heparin is combined with Deoxycholic Acid.Approved, Investigational
HydroxytyrosolThe risk or severity of adverse effects can be increased when Hydroxytyrosol is combined with Deoxycholic Acid.Investigational
IbudilastThe risk or severity of adverse effects can be increased when Ibudilast is combined with Deoxycholic Acid.Approved, Investigational
Icosapent ethylThe risk or severity of adverse effects can be increased when Icosapent ethyl is combined with Deoxycholic Acid.Approved, Nutraceutical
IdraparinuxThe risk or severity of adverse effects can be increased when Idraparinux is combined with Deoxycholic Acid.Investigational
IfenprodilThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Deoxycholic Acid.Approved, Investigational, Withdrawn
IfetrobanThe risk or severity of adverse effects can be increased when Ifetroban is combined with Deoxycholic Acid.Investigational
IloprostThe risk or severity of adverse effects can be increased when Iloprost is combined with Deoxycholic Acid.Approved, Investigational
IndobufenThe risk or severity of adverse effects can be increased when Indobufen is combined with Deoxycholic Acid.Investigational
KetanserinThe risk or severity of adverse effects can be increased when Ketanserin is combined with Deoxycholic Acid.Investigational
LepirudinThe risk or severity of adverse effects can be increased when Lepirudin is combined with Deoxycholic Acid.Approved
LetaxabanThe risk or severity of adverse effects can be increased when Letaxaban is combined with Deoxycholic Acid.Investigational
LinsidomineThe risk or severity of adverse effects can be increased when Linsidomine is combined with Deoxycholic Acid.Experimental
MelagatranThe risk or severity of adverse effects can be increased when Melagatran is combined with Deoxycholic Acid.Experimental
MilrinoneThe risk or severity of adverse effects can be increased when Milrinone is combined with Deoxycholic Acid.Approved
NadroparinThe risk or severity of adverse effects can be increased when Nadroparin is combined with Deoxycholic Acid.Approved
NafamostatThe risk or severity of adverse effects can be increased when Nafamostat is combined with Deoxycholic Acid.Approved, Investigational
NaftopidilThe risk or severity of adverse effects can be increased when Naftopidil is combined with Deoxycholic Acid.Investigational
NimesulideThe risk or severity of adverse effects can be increased when Nimesulide is combined with Deoxycholic Acid.Approved, Investigational, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with Deoxycholic Acid.Investigational
OtamixabanThe risk or severity of adverse effects can be increased when Otamixaban is combined with Deoxycholic Acid.Investigational
Pentaerythritol TetranitrateThe risk or severity of adverse effects can be increased when Pentaerythritol Tetranitrate is combined with Deoxycholic Acid.Approved
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Deoxycholic Acid.Approved
PentoxifyllineThe risk or severity of adverse effects can be increased when Pentoxifylline is combined with Deoxycholic Acid.Approved, Investigational
PhenindioneThe risk or severity of adverse effects can be increased when Phenindione is combined with Deoxycholic Acid.Approved, Investigational
PhenprocoumonThe risk or severity of adverse effects can be increased when Phenprocoumon is combined with Deoxycholic Acid.Approved, Investigational
PicotamideThe risk or severity of adverse effects can be increased when Picotamide is combined with Deoxycholic Acid.Experimental
PrasugrelThe risk or severity of adverse effects can be increased when Prasugrel is combined with Deoxycholic Acid.Approved
Protein CThe risk or severity of adverse effects can be increased when Protein C is combined with Deoxycholic Acid.Approved
Protein S humanThe risk or severity of adverse effects can be increased when Protein S human is combined with Deoxycholic Acid.Approved
ProtocatechualdehydeThe risk or severity of adverse effects can be increased when Protocatechualdehyde is combined with Deoxycholic Acid.Approved
RamatrobanThe risk or severity of adverse effects can be increased when Ramatroban is combined with Deoxycholic Acid.Investigational
ResveratrolThe risk or severity of adverse effects can be increased when Resveratrol is combined with Deoxycholic Acid.Approved, Experimental, Investigational
ReviparinThe risk or severity of adverse effects can be increased when Reviparin is combined with Deoxycholic Acid.Approved, Investigational
RidogrelThe risk or severity of adverse effects can be increased when Ridogrel is combined with Deoxycholic Acid.Approved
RivaroxabanThe risk or severity of adverse effects can be increased when Rivaroxaban is combined with Deoxycholic Acid.Approved
SarpogrelateThe risk or severity of adverse effects can be increased when Sarpogrelate is combined with Deoxycholic Acid.Investigational
SevofluraneThe risk or severity of adverse effects can be increased when Sevoflurane is combined with Deoxycholic Acid.Approved, Vet Approved
SRT501The risk or severity of adverse effects can be increased when SRT501 is combined with Deoxycholic Acid.Investigational
SulodexideThe risk or severity of adverse effects can be increased when Sulodexide is combined with Deoxycholic Acid.Approved, Investigational
TesmilifeneThe risk or severity of adverse effects can be increased when Tesmilifene is combined with Deoxycholic Acid.Investigational
TicagrelorThe risk or severity of adverse effects can be increased when Ticagrelor is combined with Deoxycholic Acid.Approved
TiclopidineThe risk or severity of adverse effects can be increased when Ticlopidine is combined with Deoxycholic Acid.Approved
TirofibanThe risk or severity of adverse effects can be increased when Tirofiban is combined with Deoxycholic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Tranilast is combined with Deoxycholic Acid.Approved, Investigational
TrapidilThe risk or severity of adverse effects can be increased when Trapidil is combined with Deoxycholic Acid.Approved
TriflusalThe risk or severity of adverse effects can be increased when Triflusal is combined with Deoxycholic Acid.Approved, Investigational
TroxerutinThe risk or severity of adverse effects can be increased when Troxerutin is combined with Deoxycholic Acid.Investigational
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Deoxycholic Acid.Approved
WarfarinThe risk or severity of adverse effects can be increased when Warfarin is combined with Deoxycholic Acid.Approved
XimelagatranThe risk or severity of adverse effects can be increased when Ximelagatran is combined with Deoxycholic Acid.Approved, Investigational, Withdrawn
Food Interactions
Not Available

References

Synthesis Reference

Filiberto Zadini, Giorgio Zadini, "Deoxycholic acid liposome-based dermatological topical preparation." U.S. Patent US20060222695, issued October 05, 2006.

US20060222695
General References
  1. Wollina U, Goldman A: ATX-101 for reduction of submental fat. Expert Opin Pharmacother. 2015 Apr;16(5):755-62. doi: 10.1517/14656566.2015.1019465. Epub 2015 Feb 27. [PubMed:25724831]
  2. Walker P, Lee D: A phase 1 pharmacokinetic study of ATX-101: serum lipids and adipokines following synthetic deoxycholic acid injections. J Cosmet Dermatol. 2015 Mar;14(1):33-9. doi: 10.1111/jocd.12122. Epub 2015 Feb 14. [PubMed:25684122]
External Links
Human Metabolome Database
HMDB00626
KEGG Compound
C04483
PubChem Compound
222528
PubChem Substance
46506360
ChemSpider
193196
BindingDB
50375599
ChEBI
28834
ChEMBL
CHEMBL406393
HET
DXC
Drugs.com
Drugs.com Drug Page
AHFS Codes
  • 92:92.00 — Other Miscellaneous Therapeutic Agents
PDB Entries
1e3v / 1fm4 / 1os6 / 2bjf / 2opx / 2w1b / 3dtu / 3o01 / 3r9v / 3rv5
show 19 more
FDA label
Download (3.18 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceCharacteristics of Subcutaneous Fat1
1CompletedTreatmentHealthy Volunteers2
2CompletedTreatmentModerate or Severe Submental Fullness1
3CompletedNot AvailableHealthy Volunteers / Submental Fat1
3CompletedTreatmentEfficacy / Healthy Volunteers / Safety / Submental Fat1
3CompletedTreatmentHealthy Volunteers / Submental Fat1
3CompletedTreatmentModerate or Severe Submental Fullness4
4CompletedTreatmentFat Reduction1
4Not Yet RecruitingTreatmentAdiposity1
Not AvailableCompletedTreatmentAbdominal Subcutaneous Fat1
Not AvailableNot Yet RecruitingTreatmentUpper Back Fat1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SolutionSubcutaneous10 mg
TabletOral
Injection, solutionSubcutaneous20 mg/2mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8546367No2008-02-212028-02-21Us
US7622130No2007-12-102027-12-10Us
US7754230No2007-12-102027-12-10Us
US8298556No2005-08-032025-08-03Us
US8846066No2005-02-082025-02-08Us
US8367649No2010-03-022030-03-02Us
US8461140No2008-02-212028-02-21Us
US8883770No2008-02-212028-02-21Us
US8653058No2010-03-022030-03-02Us
US8101593No2010-03-022030-03-02Us
US8242294No2008-05-162028-05-16Us
US9522155No2008-02-212028-02-21Us
US9636349No2008-02-212028-02-21Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)177 °CPhysProp
water solubility43.6 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.50RODA,A ET AL. (1990)
logS-3.95ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0173 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.2 m3·mol-1ChemAxon
Polarizability46.17 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9766
Blood Brain Barrier+0.9288
Caco-2 permeable+0.73
P-glycoprotein substrateSubstrate0.6648
P-glycoprotein inhibitor INon-inhibitor0.8737
P-glycoprotein inhibitor IIInhibitor0.5368
Renal organic cation transporterNon-inhibitor0.8537
CYP450 2C9 substrateNon-substrate0.7818
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9456
CYP450 2D6 inhibitorNon-inhibitor0.9781
CYP450 2C19 inhibitorNon-inhibitor0.9707
CYP450 3A4 inhibitorNon-inhibitor0.8405
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9563
Ames testNon AMES toxic0.8794
CarcinogenicityNon-carcinogens0.9329
BiodegradationNot ready biodegradable0.992
Rat acute toxicity2.5624 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9622
hERG inhibition (predictor II)Non-inhibitor0.7246
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-0006-0009000000-8b9c4803e9cb1d194c2e
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0006-0009000000-cccabd9d13ac783b6e31
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0007-2009000000-d7c20760d2074c07af22
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0006-0009000000-269a5d1ed75b71c78ecb
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, NegativeLC-MS/MSsplash10-0007-0009000000-72f1acf9f31f344daaa1
LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , NegativeLC-MS/MSsplash10-000x-0008000900-ebb0e6a61bd8f06a21f7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-0002-0009000000-8078ef73008efc65c713
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0009000000-269a5d1ed75b71c78ecb
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0007-0009000000-827a9ce119d7f2f1cb5c
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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.
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
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
bile acid, dihydroxy-5beta-cholanic acid (CHEBI:28834) / C24 bile acids, alcohols, and derivatives, Cholane and derivatives (C04483) / C24 bile acids, alcohols, and derivatives (LMST04010040)

Targets

Details
1. Steroid Delta-isomerase
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Steroid delta-isomerase activity
Specific Function
Not Available
Gene Name
ksi
Uniprot ID
P07445
Uniprot Name
Steroid Delta-isomerase
Molecular Weight
14535.48 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Geobacter sulfurreducens
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
ppcA
Uniprot ID
Q8GGK7
Uniprot Name
Cytochrome C
Molecular Weight
9747.54 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ribosome binding
Specific Function
Involved in the biogenesis of the 60S ribosomal subunit and translational activation of ribosomes. Together with SBDS, triggers the GTP-dependent release of EIF6 from 60S pre-ribosomes in the cytop...
Gene Name
EFTUD1
Uniprot ID
Q7Z2Z2
Uniprot Name
Elongation factor Tu GTP-binding domain-containing protein 1
Molecular Weight
125428.745 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Clostridium perfringens (strain 13 / Type A)
Pharmacological action
Unknown
General Function
Choloylglycine hydrolase activity
Specific Function
The enzyme catalyzes the degradation of conjugated bile acids in the mammalian gut.
Gene Name
cbh
Uniprot ID
P54965
Uniprot Name
Choloylglycine hydrolase
Molecular Weight
37185.0 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Succinate-semialdehyde dehydrogenase [nad(p)+] activity
Specific Function
Acts on lactaldehyde as well as other aldehydes.
Gene Name
aldA
Uniprot ID
P25553
Uniprot Name
Lactaldehyde dehydrogenase
Molecular Weight
52272.37 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
AcrA-AcrB-AcrZ-TolC is a drug efflux protein complex with broad substrate specificity that uses the proton motive force to export substrates.Involved in contact-dependent growth inhibition (CDI), a...
Gene Name
acrB
Uniprot ID
P31224
Uniprot Name
Multidrug efflux pump subunit AcrB
Molecular Weight
113572.75 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Rhodobacter sphaeroides
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Cytochrome c oxidase is the component of the respiratory chain that catalyzes the reduction of oxygen to water. Subunits 1-3 form the functional core of the enzyme complex. Co I is the catalytic su...
Gene Name
ctaD
Uniprot ID
P33517
Uniprot Name
Cytochrome c oxidase subunit 1
Molecular Weight
63146.395 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Rhodobacter sphaeroides
Pharmacological action
Unknown
General Function
Cytochrome-c oxidase activity
Specific Function
Subunits I and II form the functional core of the enzyme complex. Electrons originating in cytochrome c are transferred via heme a and Cu(A) to the binuclear center formed by heme a3 and Cu(B).
Gene Name
ctaC
Uniprot ID
Q03736
Uniprot Name
Cytochrome c oxidase subunit 2
Molecular Weight
32930.42 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxyla...
Gene Name
NR1H4
Uniprot ID
Q96RI1
Uniprot Name
Bile acid receptor
Molecular Weight
55913.915 Da
References
  1. Fujino T, Une M, Imanaka T, Inoue K, Nishimaki-Mogami T: Structure-activity relationship of bile acids and bile acid analogs in regard to FXR activation. J Lipid Res. 2004 Jan;45(1):132-8. Epub 2003 Sep 16. [PubMed:13130122]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
S-nitrosoglutathione binding
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name
GSTP1
Uniprot ID
P09211
Uniprot Name
Glutathione S-transferase P
Molecular Weight
23355.625 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
G-protein coupled bile acid receptor activity
Specific Function
Receptor for bile acid. Bile acid-binding induces its internalization, activation of extracellular signal-regulated kinase and intracellular cAMP production. May be involved in the suppression of m...
Gene Name
GPBAR1
Uniprot ID
Q8TDU6
Uniprot Name
G-protein coupled bile acid receptor 1
Molecular Weight
35247.795 Da
References
  1. Yoneno K, Hisamatsu T, Shimamura K, Kamada N, Ichikawa R, Kitazume MT, Mori M, Uo M, Namikawa Y, Matsuoka K, Sato T, Koganei K, Sugita A, Kanai T, Hibi T: TGR5 signalling inhibits the production of pro-inflammatory cytokines by in vitro differentiated inflammatory and intestinal macrophages in Crohn's disease. Immunology. 2013 May;139(1):19-29. doi: 10.1111/imm.12045. [PubMed:23566200]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Schuetz EG, Strom S, Yasuda K, Lecureur V, Assem M, Brimer C, Lamba J, Kim RB, Ramachandran V, Komoroski BJ, Venkataramanan R, Cai H, Sinal CJ, Gonzalez FJ, Schuetz JD: Disrupted bile acid homeostasis reveals an unexpected interaction among nuclear hormone receptors, transporters, and cytochrome P450. J Biol Chem. 2001 Oct 19;276(42):39411-8. Epub 2001 Aug 16. [PubMed:11509573]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Kullak-Ublick GA, Hagenbuch B, Stieger B, Wolkoff AW, Meier PJ: Functional characterization of the basolateral rat liver organic anion transporting polypeptide. Hepatology. 1994 Aug;20(2):411-6. [PubMed:8045503]
  2. Hata S, Wang P, Eftychiou N, Ananthanarayanan M, Batta A, Salen G, Pang KS, Wolkoff AW: Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. Am J Physiol Gastrointest Liver Physiol. 2003 Nov;285(5):G829-39. Epub 2003 Jul 3. [PubMed:12842829]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Bile acid:sodium symporter activity
Specific Function
Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism.
Gene Name
SLC10A2
Uniprot ID
Q12908
Uniprot Name
Ileal sodium/bile acid cotransporter
Molecular Weight
37713.405 Da
References
  1. Craddock AL, Love MW, Daniel RW, Kirby LC, Walters HC, Wong MH, Dawson PA: Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. Am J Physiol. 1998 Jan;274(1 Pt 1):G157-69. [PubMed:9458785]
  2. Saeki T, Matoba K, Furukawa H, Kirifuji K, Kanamoto R, Iwami K: Characterization, cDNA cloning, and functional expression of mouse ileal sodium-dependent bile acid transporter. J Biochem. 1999 Apr;125(4):846-51. [PubMed:10101301]
  3. Saeki T, Takahashi N, Kanamoto R, Iwami K: Characterization of cloned mouse Na+/taurocholate cotransporting polypeptide by transient expression in COS-7 cells. Biosci Biotechnol Biochem. 2002 May;66(5):1116-8. [PubMed:12092825]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Virus receptor activity
Specific Function
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
Gene Name
SLC10A1
Uniprot ID
Q14973
Uniprot Name
Sodium/bile acid cotransporter
Molecular Weight
38118.64 Da
References
  1. Hata S, Wang P, Eftychiou N, Ananthanarayanan M, Batta A, Salen G, Pang KS, Wolkoff AW: Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake. Am J Physiol Gastrointest Liver Physiol. 2003 Nov;285(5):G829-39. Epub 2003 Jul 3. [PubMed:12842829]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 17:18