MADECASSIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H48O6
Molecular Weight	504.6985
Optical Activity	UNSPECIFIED
Defined Stereocenters	13 / 13
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CC=C3[C@]4([H])[C@@H](C)[C@H](C)CC[C@@]4(CC[C@@]3(C)[C@]1(C)C[C@@H](O)[C@@]5([H])[C@](C)(CO)[C@@H](O)[C@H](O)C[C@]25C)C(O)=O

InChI

InChIKey=PRAUVHZJPXOEIF-AOLYGAPISA-N

InChI=1S/C30H48O6/c1-16-9-10-30(25(35)36)12-11-28(5)18(22(30)17(16)2)7-8-21-26(3)13-20(33)24(34)27(4,15-31)23(26)19(32)14-29(21,28)6/h7,16-17,19-24,31-34H,8-15H2,1-6H3,(H,35,36)/t16-,17+,19-,20-,21-,22+,23-,24+,26-,27+,28-,29-,30+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C30H48O6
Molecular Weight	504.6985
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	13 / 13
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26633490 | https://www.ncbi.nlm.nih.gov/pubmed/19774506 | https://www.ncbi.nlm.nih.gov/pubmed/25685908 | https://www.ncbi.nlm.nih.gov/pubmed/27446228

Madecassic acid is a naturally produced terpene from Centella asiatica. It has demonstrated anti-inflammatory and anti-diabetic effects by blocking NF-kB activation and altering lipid metabolism in mice. Madecassic acid has also shown anti-tumor effects in a mouse model of colon cancer; and, was demonstrated in vitro to stimulate the growth of neurofilaments from rat PC1 cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
regulation of NIK/NF-kappaB signaling 2 Target ID: GO:1901222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19774506	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26633490	Primary	Preclinical	Unknown Approved Use Unknown
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24965394	Primary	Preclinical	Unknown Approved Use Unknown
Burn 40 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23346217	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Isolation of a new triterpenic acid from Centella asiatica (L.) Urb. of Madagascar: madecassic acid].	1967 Jan 9	4961798
Anti-inflammatory effects of madecassic acid via the suppression of NF-kappaB pathway in LPS-induced RAW 264.7 macrophage cells.	2010 Feb	19774506
Anti-Diabetic Effects of Madecassic Acid and Rotundic Acid.	2015 Dec 2	26633490
Structural analysis of metabolites of asiatic acid and its analogue madecassic acid in zebrafish using LC/IT-MSn.	2015 Feb 12	25685908
Identification of Centella asiatica's Effective Ingredients for Inducing the Neuronal Differentiation.	2016	27446228

Patents

Sample Use Guides

In Vivo Use Guide

In a preclinical study, diabetic male Balb/cA mice were fed a diet including 0.05% and 0.1% madecassic acid by mass for six weeks.

Route of Administration: Oral

In Vitro Use Guide

Pheochromocytoma PC1 cells from rat adrenal medulla were maintained in Dulbecco's modified Eagle's medium. Madecassic acid at 40.8 uM was applied to PC12 cells for 72 hours on its own and in combination with 14.4 uM Asiatic acid. Madecassic acid showed moderate effects on neurofilament expression (monitored by microscopy). However, the combination delivered superior induction on the expression of NF68 and NF200 (monitored by western blot) compared to either on its own.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:36:37 UTC 2023` Edited by `admin` on `Sat Dec 16 01:36:37 UTC 2023`
Record UNII	M7O1N24J82
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MADECASSIC ACID

Official Name

English

MADECASSIC ACID (CONSTITUENT OF CENTELLA ASIATICA) [DSC]

Common Name

English

MADECASSIC ACID [INCI]

Common Name

English

6.BETA.-HYDROXYASIATIC ACID

Common Name

English

ORISTRACT MDA

Brand Name

English

Madecassic acid [WHO-DD]

Common Name

English

BRAHMIC ACID

Common Name

English

URS-12-EN-28-OIC ACID, 2,3,6,23-TETRAHYDROXY-, (2.ALPHA.,3.BETA.,4.ALPHA.,6.BETA.)-

Common Name

English

NSC-88135

Code

English

2.ALPHA.,3.BETA.,6.BETA.,23-TETRAHYDROXY-URS-12-EN-28-OIC ACID

Common Name

English

URS-12-EN-28-OIC ACID, 2.ALPHA.,3.BETA.,6.BETA.,23-TETRAHYDROXY-

Common Name

English

Code System Code Type Description

RXCUI

1551573