METHYL CHOLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H42O5
Molecular Weight	422.598
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=DLYVTEULDNMQAR-SRNOMOOLSA-N

InChI=1S/C25H42O5/c1-14(5-8-22(29)30-4)17-6-7-18-23-19(13-21(28)25(17,18)3)24(2)10-9-16(26)11-15(24)12-20(23)27/h14-21,23,26-28H,5-13H2,1-4H3/t14-,15+,16-,17-,18+,19+,20-,21+,23+,24+,25-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C25H42O5
Molecular Weight	422.598
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15283464

Methyl cholate is a cholesterol biosynthesis inhibitor. It exhibited inhibitory effect on the later step of cholesterol biosynthesis, indicating that its action mode is different from that of statins that act on the HMG-CoA reductase.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bile acid receptor FXR 29 Target ID: CHEMBL2047 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18603830	Agonist 2752
Cholesterol Biosynthesis 2 Target ID: WP197 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15283464	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Biotransformation of methyl cholate by Aspergillus niger.	2008-09-05	19428436
The novel compounds that activate farnesoid X receptor: the diversity of their effects on gene expression.	2008-07	18603830
OATP8/1B3-mediated cotransport of bile acids and glutathione: an export pathway for organic anions from hepatocytes?	2006-10-13	16877380
Selective acylation of cholic acid derivatives with multiple methacrylate groups.	2005-07	15894037
A cholesterol biosynthesis inhibitor from Rhizopus oryzae.	2004-06	15283464
Mixed steroidal 1,2,4,5-tetraoxanes: antimalarial and antimycobacterial activity.	2002-08-01	12139444

Patents

Sample Use Guides

In Vivo Use Guide

At least 15 patients reported by Gonzales et al. (2009), have been treated, most of them for more than 10 years, with cholic acid preparations that have contained between 0.4 to 0.5% of methyl cholate.

Route of Administration: Unknown

In Vitro Use Guide

A study in oesophageal cells has demonstrated no genotoxicity for methyl cholate at concentrations of 25 to 200 uM test.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:09:18 GMT 2025` Edited by `admin` on `Mon Mar 31 22:09:18 GMT 2025`
Record UNII	E1P59HQX4Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHYL CHOLATE

Common Name

English

NSC-126794

Preferred Name

English

CHOLAN-24-OIC ACID, 3,7,12-TRIHYDROXY-, METHYL ESTER, (3.ALPHA.,5.BETA.,7.ALPHA.,12.ALPHA.)

Systematic Name

English

METHYL CHOLATE, (+)-

Common Name

English

CHOLIC ACID, METHYL ESTER

Common Name

English

METHYL 3.ALPHA.,7.ALPHA.,12.ALPHA.-TRIHYDROXY-5.BETA.-CHOLANOATE

Systematic Name

English

Code System Code Type Description

PUBCHEM

10960835