CHOLANIC ACID, (5.BETA.)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H40O2
Molecular Weight	360.5732
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=RPKLZQLYODPWTM-LVVAJZGHSA-N

InChI=1S/C24H40O2/c1-16(7-12-22(25)26)19-10-11-20-18-9-8-17-6-4-5-14-23(17,2)21(18)13-15-24(19,20)3/h16-21H,4-15H2,1-3H3,(H,25,26)/t16-,17+,18+,19-,20+,21+,23+,24-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17136858 | https://www.ncbi.nlm.nih.gov/pubmed/24152675 | https://www.ncbi.nlm.nih.gov/pubmed/23716494 | https://www.ncbi.nlm.nih.gov/pubmed/26169917

Cholanic acid is the archetypal C24 bile acid skeleton from which all other C24 bile acids can be derived. Of the two common isomers: 5alpha and 5Beta, the last isomer is the most biologically relevant. 5-Beta Cholanic Acid has been studied as a modulator of the gamma-secretase complex as it pertains to Alzheimer's disease; it has also been identified as an inhibitor of the Ephrin type-A receptor 2 that is involved in cancer cell signaling and angiogenesis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Ephrin type-A receptor 2 6 Target ID: P29317 Gene ID: 1969.0 Gene Symbol: EPHA2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24152675	Antagonist 2778		4.91 null [pIC50]
Gamma-secretase 21 Target ID: CHEMBL2094135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26169917 \| https://www.ncbi.nlm.nih.gov/pubmed/23716494	Modulator 828		5.7 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24152675	Primary		Not Provided 504	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23716494 https://www.ncbi.nlm.nih.gov/pubmed/26169917	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Cholestenoic acid, an endogenous cholesterol metabolite, is a potent γ-secretase modulator.	2015 Jul 14	26169917

Patents

Sample Use Guides

In Vivo Use Guide

C14 labeled cholanic acid sodium salt was administered intraperitoneally at a dose of 0.7 mg (1.54 x 10^6 d.p.m. per mg) to rats with bile fistulas, and rats with ligated bile ducts. The excreta was monitored for C14 labeled metabolites.

Route of Administration: Intraperitoneal

In Vitro Use Guide

PC3 human prostate adenocarcinoma cells were grown in Ham F12 media. 5B-cholanic acid was stocked as 5 mM solution in DMSO and tested in a 96 well ELISA displacement assay starting at 50 microM.

Name

Type

Language

CHOLANIC ACID, (5.BETA.)-

Common Name

English

5.BETA.-CHOLAN-24-OIC ACID

Systematic Name

English

CHOLAN-24-OIC ACID, (5.BETA.)-

Systematic Name

English

L-596205-0

Code

English

5.BETA.-CHOLANIC ACID

Systematic Name

English

NSC-18161

Code

English

5.BETA.-CHOLANOIC ACID

Systematic Name

English

URSOCHOLANIC ACID

Common Name

English

CHOLANIC ACID, 5.BETA.-

Common Name

English

Code System Code Type Description

PUBCHEM

92803