friedelin

Also known as (-)-friedelin, friedeline, D:A-friedooleanan-3-one, friedelan-3-one

Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant. It is noted as having antimicrobial properties and has been recovered from the byproducts of corkboard manufacturing. The compound is also a biological precursor of celastrol. It is considered a friedelane-type compound, appearing structurally similar with the addition of a ketone group.

Chemical data

Formula: C30H50O
Molecular weight: 426.7 g/mol
IUPAC name: (4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bS)-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
SMILES: C[C@H]1C(=O)CC[C@@H]2[C@@]1(CC[C@H]3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C)C)C)C)C
InChIKey: OFMXGFHWLZPCFL-SVRPQWSVSA-N
XLogP: 9.8
Polar surface area: 17.1 Å²
H-bond donors: 0
H-bond acceptors: 1
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 426.386166

Show 3 more facts

chemical formula: C₃₀H₅₀O
canonical SMILES: CC1C(=O)CCC2C1(CCC3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C)C)C)C)C)C
isomeric SMILES: C[C@H]1C(=O)CC[C@@H]2[C@@]1(CC[C@H]3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C)C)C)C)C

Sources (4)

via Wikidata · CC0

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