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Compound Detail

CHEMBL406393

DEOXYCHOLIC ACID
💊 Approved Drug
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💊 Approved Drug
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL406393
Name DEOXYCHOLIC ACID
Phase Approved
Structure Type MOL
InChI Key KXGVEGMKQFWNSR-LLQZFEROSA-N
Therapeutic ✓ Yes

Known Names

Acide desoxycholique Acido desoxicolico ATX-101 ATX-101 (DEOXYCHOLIC ACID) Deoxycholic acid Desoxycholic acid DWJ-211 DWJ211 Kybella NSC-8797
7
Targets
17
Activities
4
Assay Types
0
PK Parameters
20
Publications
10
Known Names
5
Indications
1
Mechanisms

Molecular Properties

392.6
MW (Da)
4.48
ALogP
3
HBA
3
HBD
77.8
PSA (Ų)
0.66
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2015
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Year 2013

Extended Properties

Molecular Formula C24H40O4
MW 392.58
Aromatic Rings 0
Heavy Atoms 28
NP-Likeness 2.70

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cell membrane disrupting agent DISRUPTING AGENT Cell membrane ✓ ✓

Indications

Lipoma Pain Neurofibroma Neurofibromatosis 1 Obesity

ATC Classification

D11AX24
deoxycholic acid
Level 1: DERMATOLOGICALS
Level 2: OTHER DERMATOLOGICAL PREPARATIONS

Activity Summary

EC50 11 meas. best 6.0
IC50 2 meas. best 4.08
Kd 2 meas. best 4.8
Ki 2 meas. best 5.2

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
G-protein coupled bile acid receptor 1
CHEMBL5409
 EC50 6.0 5.95 1010.0 2
Unchecked
CHEMBL612545
 EC50 5.78 5.1067 1680.0 6
Ileal sodium/bile acid cotransporter
CHEMBL2778
 Ki 5.2 5.2 6300.0 2
Steroid Delta-isomerase
CHEMBL2321641
 Kd 4.8 4.8 16000.0 2
Bile acid receptor
CHEMBL2047
 EC50 4.35 4.325 45000.0 2
HuTu80
CHEMBL614582
 IC50 4.08 4.08 82900.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.03 4.03 93600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
G-protein coupled bile acid receptor 1 EC50 = 1010.0 nM 6.0 Agonist activity at human TGR5 38691888
G-protein coupled bile acid receptor 1 EC50 = 1250.0 nM 5.9 Agonist activity at human TGR5 expressed in CHO cells by luciferase assay 18307294
Unchecked EC50 = 1680.0 nM 5.78 Agonist activity at MRGPRX4 83S (unknown origin) expressed in CHO-K1 cells asses... 37967029
Unchecked EC50 = 2600.0 nM 5.58 Agonist activity at MRGPRX4 83L (unknown origin) expressed in HEK293 cells co-ex... 37967029
Ileal sodium/bile acid cotransporter Ki = 6300.0 nM 5.2 TP_TRANSPORTER: inhibition of Taurocholate uptake in ASBT-expressing COS cells 9458785
Ileal sodium/bile acid cotransporter Ki = 6300.0 nM 5.2 TP_TRANSPORTER: inhibition of Taurocholate uptake in ASBT-expressing COS cells 9458785
Unchecked EC50 = 11200.0 nM 4.95 Agonist activity at MRGPRX4 83L (unknown origin) expressed in human 1321N1 gliob... 37967029
Unchecked EC50 = 11200.0 nM 4.95 Agonist activity at MRGPRX4 83L expressed in human HEK293 cells co- expressing G... 37975421
Steroid Delta-isomerase Kd = 16000.0 nM 4.8 Binding affinity to Pseudomonas putida KSI by surface plasmon resonance analysis 23419007
Steroid Delta-isomerase Kd = 16000.0 nM 4.8 Binding affinity to Pseudomonas putida KSI by isothermal titration calorimetry 23419007
Unchecked EC50 = 16900.0 nM 4.77 Agonist activity at MRGPRX4 83S expressed in human HEK293 cells co- expressing G... 37975421
Unchecked EC50 = 24600.0 nM 4.61 Agonist activity at MRGPRX4 83L (unknown origin) expressed in CHO cells assessed... 37967029
Bile acid receptor EC50 = 45000.0 nM 4.35 Agonist activity at GST-tagged FXR-LBD (unknown origin) assessed as biotin-label... 29275233
Bile acid receptor EC50 = 50000.0 nM 4.3 Agonist activity at human recombinant FXR expressed in HEK293 cells coexpressing... 22583617
HuTu80 IC50 = 82900.0 nM 4.08 Antiproliferative activity against human HuTu 80 cells after 24 hrs by MTT assay 28688958
Plasmodium falciparum IC50 = 93600.0 nM 4.03 Antiplasmodial activity against Plasmodium falciparum 3D7 assessed as reduction ... 26063305

Literature References

PubMed DOI Target Context # Activities
20211889 10.1128/aac.01677-09 Escherichia coli 20
- 10.6019/CHEMBL5303304 U2OS 8
17548499 10.1128/aac.00339-07 Escherichia coli 7
- 10.6019/CHEMBL5303304 Fibroblast 7
18725450 10.1128/aac.00245-08 Pasteurella multocida 7
30108740 10.1039/C7MD00475C Danio rerio 6
19770280 10.1128/aac.00748-09 Escherichia coli 5
37967029 10.1021/acs.jmedchem.3c01013 Unchecked 5
28688958 10.1016/j.bmcl.2017.06.072 Unchecked 5
19770280 10.1128/aac.00748-09 Acinetobacter baumannii 4
39149112 10.1039/d4md00007b Plasmodium falciparum 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
8045503 10.1016/0270-9139(94)90194-5 Solute carrier organic anion transporter family member 1A1 4
26774929 10.1016/j.ejmech.2016.01.002 Vitamin D3 receptor 4
33904732 10.1021/acs.jnatprod.0c01327 Unchecked 3
20713311 10.1016/j.bmc.2010.07.030 ADMET 3
33904732 10.1021/acs.jnatprod.0c01327 G-protein coupled bile acid receptor 1 3
27448915 10.1016/j.ejmech.2016.04.055 NON-PROTEIN TARGET 3
30108740 10.1039/C7MD00475C HUVEC 3
26063305 10.1016/j.ejmech.2015.05.044 ADMET 3

Data from ChEMBL 36 via Core Engine