Lithocholic acid - >97.0%, high purity , CAS No.434-13-9, Agonist of Farnesoid X receptor;Agonist of GPBA receptor;Agonist of Pregnane X receptor;Agonist of Vitamin D receptor

Item Number
L106779
Grouped product items
SKUSizeAvailabilityPrice Qty
L106779-1g
1g
In stock
$64.90
L106779-5g
5g
In stock
$103.90
L106779-25g
25g
In stock
$468.90
L106779-100g
100g
In stock
$1,684.90

Basic Description

SynonymsNCGC00259417-01 | 3alpha-Hydroxy-5beta-cholanate | CCRIS 363 | 17-beta-(1-Methyl-3-carboxypropyl)ethiocholan-3-alpha-ol | 3.alpha.-Hydroxy-5.beta.-cholanic acid | (3beta,5beta,14beta,17alpha)-3-Hydroxycholan-24-Oic Acid | A-cholanic acid | Lithocholic Aci
Specifications & PurityMoligand™, ≥97%
Shipped InNormal
GradeMoligand™
Action TypeAGONIST
Mechanism of actionAgonist of Farnesoid X receptor;Agonist of GPBA receptor;Agonist of Pregnane X receptor;Agonist of Vitamin D receptor

Associated Targets(Human)

VDR Tclin Vitamin D3 receptor (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
NR1H4 Tclin Bile acid receptor (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
NR1I2 Tchem Nuclear receptor subfamily 1 group I member 2 (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
GPBAR1 Tchem G-protein coupled bile acid receptor 1 (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
VDR Tclin Vitamin D receptor (26531 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RXRA Tclin Retinoid X receptor alpha (3637 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CXCL8 Tchem Interleukin-8 (642 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTPN2 Tchem T-cell protein-tyrosine phosphatase (1317 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CSNK1D Tchem Casein kinase I delta (4546 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR1H4 Tclin Bile acid receptor FXR (6228 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
S1PR1 Tclin Sphingosine 1-phosphate receptor Edg-1 (5806 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR1I2 Tchem Pregnane X receptor (6667 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CASP7 Tchem Caspase-7 (3146 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
C5AR1 Tclin C5a anaphylatoxin chemotactic receptor (2677 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TP53 Tchem Cellular tumor antigen p53 (48468 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EPHA2 Tclin Ephrin type-A receptor 2 (3499 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A498 (42825 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHN (49357 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Caco-2 (12174 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAKI-1 (44928 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
COLO 205 (50209 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GBM (188 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-1080 (3966 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Huh-7 (12904 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KM12 (47707 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LoVo (4724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
M14 (47487 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MOLT-4 (49676 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-3 (48710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Aplnr Apelin receptor (201 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ppard Peroxisome proliferator-activated receptor delta (358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mapk1 MAP kinase ERK2 (650 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hdac6 Histone deacetylase 6 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Fgfr3 Fibroblast growth factor receptor 3 (21 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Clostridioides difficile (2968 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei brucei (13300 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc10a1 Bile acid transporter (65 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GCN5 Histone acetyltransferase GCN5 (89 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Gpr119 Glucose-dependent insulinotropic receptor (270 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Danio rerio (3092 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Large T antigen (1457 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mapt Microtubule-associated protein tau (6 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rorc Nuclear receptor ROR-gamma (89407 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slco1a4 Solute carrier organic anion transporter family member 1A4 (114 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc10a2 Ileal sodium/bile acid cotransporter (17 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc10a1 Sodium/bile acid cotransporter (19 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Napepld N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D (16 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
vdra Vitamin D3 receptor A (38 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
groL GroEL/GroES (1042 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
groEL 60 kDa chaperonin (64 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

Pubchem Sid488181047
Pubchem Sid Urlhttps://pubchem.ncbi.nlm.nih.gov/substance/488181047
IUPAC Name (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
INCHI InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1
InChi Key SMEROWZSTRWXGI-HVATVPOCSA-N
Canonical SMILES CC(CCC(=O)O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
Isomeric SMILES C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C
WGK Germany 2
RTECS FZ2275000
PubChem CID 9903
Molecular Weight 376.57
Beilstein 3217757

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Find and download the COA for your product by matching the lot number on the packaging.

20 results found

Lot NumberCertificate TypeDateItem
G2431271Certificate of AnalysisJul 22, 2024 L106779
G2431270Certificate of AnalysisJul 22, 2024 L106779
G2431269Certificate of AnalysisJul 22, 2024 L106779
K2316404Certificate of AnalysisNov 09, 2023 L106779
K2316403Certificate of AnalysisNov 09, 2023 L106779
K2316281Certificate of AnalysisNov 09, 2023 L106779
K2316280Certificate of AnalysisNov 09, 2023 L106779
K2316279Certificate of AnalysisNov 09, 2023 L106779
K2316278Certificate of AnalysisNov 09, 2023 L106779
K2316277Certificate of AnalysisNov 09, 2023 L106779
G2422470Certificate of AnalysisNov 09, 2023 L106779
F2329306Certificate of AnalysisMar 03, 2023 L106779
C2315544Certificate of AnalysisMar 03, 2023 L106779
C2314349Certificate of AnalysisMar 03, 2023 L106779
C2314348Certificate of AnalysisMar 03, 2023 L106779
C2314345Certificate of AnalysisMar 03, 2023 L106779
C2314343Certificate of AnalysisMar 03, 2023 L106779
C2314336Certificate of AnalysisMar 03, 2023 L106779
C2314333Certificate of AnalysisMar 03, 2023 L106779
C2314325Certificate of AnalysisMar 03, 2023 L106779

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Chemical and Physical Properties

Specific Rotation[α]35.5°
Melt Point(°C)183-188°C

Safety and Hazards(GHS)

Pictogram(s) GHS07
Signal Warning
Hazard Statements

H315:Causes skin irritation

H319:Causes serious eye irritation

H335:May cause respiratory irritation

Precautionary Statements

P261:Avoid breathing dust/fume/gas/mist/vapors/spray.

P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing.

P280:Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352:IF ON SKIN: wash with plenty of water.

P321:Specific treatment (see ... on this label).

P405:Store locked up.

P501:Dispose of contents/container to ...

P264:Wash hands [and …] thoroughly after handling.

P271:Use only outdoors or in a well-ventilated area.

P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P403+P233:Store in a well-ventilated place. Keep container tightly closed.

P362+P364:Take off contaminated clothing and wash it before reuse.

P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes.

P337+P317:If eye irritation persists: Get medical help.

P332+P317:If skin irritation occurs: Get medical help.

P319:Get medical help if you feel unwell.

WGK Germany 2
RTECS FZ2275000

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2. Yan Ma, Yang Cao, Xiaocui Song, Weichen Xu, Zichen Luo, Jinjun Shan, Jingjie Zhou.  (2023)  Integration of semi-empirical MS/MS library with characteristic features for the annotation of novel amino acid-conjugated bile acids.  ANALYST,  148  (21): (5380-5389).  [PMID:37743718] [10.1039/D3AN01237A]
3. Qian Zhang, Wenchao Ye, Guojiao Li, Yanli Gong, Wenlang Liang, Yongxiang Leng.  (2023)  Nanotubular-aerogel/hydrogel hybrid for strain sensing applications.  Journal of Materials Chemistry C,      [PMID:] [10.1039/D3TC01866K]
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6. Jiating Zheng, Xiaoru Peng, Taifeng Zhu, Shuyao Huang, Chao Chen, Guosheng Chen, Shuqin Liu, Gangfeng Ouyang.  (2022)  Detection of bile acids in small volume human bile samples via an amino metal-organic framework composite based solid-phase microextraction probe.  JOURNAL OF CHROMATOGRAPHY A,  1685  (463634).  [PMID:36345074] [10.1016/j.chroma.2022.463634]
7. Wei Xu, Yingying Kong, Tuo Zhang, Zhihua Gong, Wenjun Xiao.  (2022)  L-Theanine regulates lipid metabolism by modulating gut microbiota and bile acid metabolism.  JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE,  103  (3): (1283-1293).  [PMID:36087337] [10.1002/jsfa.12222]
8. Ma Wen, Yang Bingxin, Li Jun, Liu Mingxia, Li Xianjiang, Liu Huwei.  (2022)  Maltose-functional metal–organic framework assisted laser desorption/ionization mass spectrometry for small biomolecule determination.  MICROCHIMICA ACTA,  189  (7): (1-8).  [PMID:35689150] [10.1007/s00604-022-05338-x]
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10. Ding Shen, Wei Hu, Suqing Zhao, Chuanbin Mao.  (2021)  Rapid Naked-Eye Detection of a Liver Disease Biomarker by Discovering Its Monoclonal Antibody to Functionalize Engineered Red-Colored Bacteria Probes.  ACS Omega,  (47): (32005–32010).  [PMID:34870023] [10.1021/acsomega.1c04779]
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17. Ke Zhou, Shao-Chun Chen, Fan Yang, Stijn van der Veen, Yue-Ping Yin.  (2020)  Impact of the gonococcal FC428 penA allele 60.001 on ceftriaxone resistance and biological fitness.  Emerging Microbes & Infections,  (1): (1219-1229).  [PMID:32438866] [10.1080/22221751.2020.1773325]
18. Xia Lu, Zhefeng Fan.  (2019)  Determination of cholic acid in body fluids by β‑cyclodextrin-modified N-doped carbon dot fluorescent probes.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,  216  (342).  [PMID:30921656] [10.1016/j.saa.2019.03.066]
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22. Dan Wang, Li Bie, Yanbin Su, Haoran Xu, Fengrong Zhang, Yanwen Su, Bo Zhang.  (2018)  Effect of lithocholic acid on biologically active α,β-unsaturated aldehydes induced by H2O2 in glioma mitochondria for use in glioma treatment.  INTERNATIONAL JOURNAL OF MOLECULAR MEDICINE,  41  (6): (3195-3202).  [PMID:29512691] [10.3892/ijmm.2018.3530]
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References

1. Incerti M, Tognolini M, Russo S, Pala D, Giorgio C, Hassan-Mohamed I, Noberini R, Pasquale EB, Vicini P, Piersanti S et al..  (2013)  Amino acid conjugates of lithocholic acid as antagonists of the EphA2 receptor..  J Med Chem,  56  (7): (2936-47).  [PMID:23489211] [10.1021/op500134e]
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