CEANOTHIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H46O5
Molecular Weight	486.6832
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@]5(C)[C@@H](CC[C@@]34C)C(C)(C)[C@@H](O)[C@@H]5C(O)=O)[C@@H]12)C(O)=O

InChI

InChIKey=WLCHQSHZHFLMJH-VILVJDKQSA-N

InChI=1S/C30H46O5/c1-16(2)17-10-13-30(25(34)35)15-14-27(5)18(21(17)30)8-9-20-28(27,6)12-11-19-26(3,4)23(31)22(24(32)33)29(19,20)7/h17-23,31H,1,8-15H2,2-7H3,(H,32,33)(H,34,35)/t17-,18+,19-,20-,21+,22+,23-,27+,28+,29-,30-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C30H46O5
Molecular Weight	486.6832
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/9834149
Curator's Comment: Description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/9730010 http://pubs.acs.org/doi/abs/10.1021/ja01268a024

Ceanothic acid, a substance previously isolated by Julian, Pikl, and Dawson, has been shown to be a triterpenoid related to the lupeol–betulin group, but in which ring A is five-membered. It has been degraded to the keto ester A norbetulonic acid methyl ester, a substance of defined constitution and stereochemistry. A recent study revealed that Paliurus ramossisimus (Rhamnaceae) is rich in ceanothic acid. Ceanothic Acid shows potent cytotoxicity on OVCAR-3, HeLa, and FS-5 Cells

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Preparation and cytotoxic effect of ceanothic acid derivatives.	1998-11	9834149
In vitro cytotoxic activity of 1-decarboxy-3-oxo-ceanothic acid in a human ovarian adenocarcinoma cell line.	1998-06	9730010

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Ceanothic Acid (10 ug/mL) shows potent cytotoxicity on OVCAR-3, HeLa, and FS-5 Cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:00:41 GMT 2025` Edited by `admin` on `Mon Mar 31 22:00:41 GMT 2025`
Record UNII	38P86ZU018
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2.ALPHA.-CARBOXY-3.BETA.-HYDROXY-A(1)-NORLUP-20(29)-EN-28-OIC ACID

Preferred Name

English

CEANOTHIC ACID

Common Name

English

EMMOLIC ACID

Common Name

English

3'H-CYCLOPENTA(3,4)-18-NORANDROST-3-ENE-3',13-DICARBOXYLIC ACID, TETRAHYDRO-4'-HYDROXY-4,5',5',9-TETRAMETHYL-15-(1-METHYLETHENYL)-, (3.BETA.,3'.BETA.,4.ALPHA.,4'.ALPHA.,5.BETA.,8.ALPHA.,9.BETA.,10.ALPHA.,13.ALPHA.,14.BETA.,15.BETA.)-

Common Name

English

CEANOTHIC ACID [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

161352