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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 of FRIEDELIN

SMILES

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

Molecular Formula C30H50O
Molecular Weight 426.7174
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
1.8 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

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.
Substance Class Chemical
Record UNII
AK21264UAD
Record Status Validated (UNII)
Record Version