FRIEDELIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H50O
Molecular Weight	426.7174
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=OFMXGFHWLZPCFL-SVRPQWSVSA-N

InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22+,23-,24+,26+,27+,28-,29+,30-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23561182 | https://www.ncbi.nlm.nih.gov/pubmed/21718291 | https://www.google.com/patents/EP2070906A1

Friedelin is a natural compound with promising proprieties. On its own or with chemical modification it is possible to introduce relevant biological activities, e.g. anti-cancer, anti-aging and agrochemical. Its availability in significant amounts has been a major drawback on its regular use and in the pursuit of different applications. Cork and cork-derived materials (e.g. black condensate) are the most relevant sources of Friedelin in nature (up to 10% in concentration). Friedelin has being shown to possess marked antioxidant and liver protective effects. Friedelin has also being demonstrated to possess potent anti-inflammatory, analgesic and antipyretic activities.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
MCF7 21 Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28619518	Inhibitor 8297		1.8 µM [IC50]
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28619518	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28619518 https://www.researchgate.net/publication/273251110_Anticancer_Activity_of_Friedelin_Isolated_from_Ethanolic_Leaf_Extract_of_Cassia_tora_on_HeLa_and_HSC-1_Cell_Lines https://www.google.ru/url?sa=t&rct=j&q=&esrc=s&source=web&cd=1&ved=0ahUKEwi2wZaI2NnWAhXBYpoKHVC4Dp8QFggoMAA&url=https%3A%2F%2Fwww.ajol.info%2Findex.php%2Fajb%2Farticle%2Fdownload%2F92284%2F81737&usg=AOvVaw39P60-PKxXaR3XCl1kUr-J	Primary	Basic research	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21718291	Primary	Preclinical	Unknown Approved Use Unknown
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21718291	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Anti-inflammatory, analgesic and antipyretic effects of friedelin isolated from Azima tetracantha Lam. in mouse and rat models.	2011 Aug	21718291

Patents

Sample Use Guides

In Vivo Use Guide

Pre-treatment of rats with friedelin at 40 mg/kg for 7 days showed liver protection.

Route of Administration: Oral

In Vitro Use Guide

Friedelin potentially inhibit 78% of MCF-7 cell's growth, the IC50 value was 1.8uM in 24h and 1.2uM in 48h. 52% apoptotic cells and 6% necrotic cells in PI, AO/ErBr staining after 48h treatment with 1.2uM of friedelin were found.

Name

Type

Language

FRIEDELIN

Common Name

English

3(2H)-PICENONE, EICOSAHYDRO-4,4A,6B,8A,11,11,12B,14A-OCTAMETHYL-, (4R-(4.ALPHA.,4A.ALPHA.,6A.BETA.,6B.ALPHA.,8A.ALPHA.,12A.ALPHA.,12B.BETA.,14A.ALPHA.,14B.BETA.))-

Systematic Name

English

FRIEDELIN [MI]

Common Name

English

3-OXOFRIEDELANE

Common Name

English

FRIEDELINE

Common Name

English

NSC-55141

Code

English

(-)-FRIEDELIN

Common Name

English

FRIEDELANONE

Common Name

English

FRIEDELAN-3-ONE

Common Name

English

24,25,26-TRINOROLEANAN-3-ONE, 5,9,13-TRIMETHYL-, (4.BETA.,5.BETA.,8.ALPHA.,9.BETA.,10.ALPHA.,13.ALPHA.,14.BETA.)-

Systematic Name

English

Code System Code Type Description

CHEBI

5171