CHEBI:5171 - friedelin

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ChEBI Name friedelin
ChEBI ID CHEBI:5171
Definition A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C30H50O
Net Charge 0
Average Mass 426.71740
Monoisotopic Mass 426.386
InChI 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
InChIKey OFMXGFHWLZPCFL-SVRPQWSVSA-N
SMILES [H][C@@]12CCC(=O)[C@H](C)[C@@]1(C)CC[C@@]1([H])[C@@]2(C)CC[C@@]2(C)[C@]3([H])CC(C)(C)CC[C@]3(C)CC[C@]12C
Roles Classification
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): anti-inflammatory drug
A substance that reduces or suppresses inflammation.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing friedelin (CHEBI:5171) has role anti-inflammatory drug (CHEBI:35472)
friedelin (CHEBI:5171) has role antipyretic (CHEBI:35493)
friedelin (CHEBI:5171) has role non-narcotic analgesic (CHEBI:35481)
friedelin (CHEBI:5171) has role plant metabolite (CHEBI:76924)
friedelin (CHEBI:5171) is a cyclic terpene ketone (CHEBI:36130)
friedelin (CHEBI:5171) is a pentacyclic triterpenoid (CHEBI:25872)
Incoming 1β-hydroxyfriedelin (CHEBI:70415) has functional parent friedelin (CHEBI:5171)
3β-hydroxyfriedelan-23-oic acid (CHEBI:70416) has functional parent friedelin (CHEBI:5171)
acetyl aleuritolic acid (CHEBI:70418) has functional parent friedelin (CHEBI:5171)
friedelin-3,4-lactone (CHEBI:70417) has functional parent friedelin (CHEBI:5171)
maytenfolone A (CHEBI:66686) has functional parent friedelin (CHEBI:5171)
IUPAC Name
(4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethylicosahydropicen-3(2H)-one
Synonyms Sources
(−)-friedelin ChEBI
D:A-friedooleanan-3-one ChemIDplus
friedelan-3-one ChemIDplus
friedelin UniProt
friedeline ChemIDplus
Database Links Databases
C00003747 KNApSAcK
C08626 KEGG COMPOUND
CPD-13047 MetaCyc
WO2009072916 Patent
View more database links
Registry Numbers Types Sources
559-74-0 CAS Registry Number KEGG COMPOUND
559-74-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17639555 PubMed citation Europe PMC
20610397 PubMed citation Europe PMC
20675291 PubMed citation Europe PMC
21718291 PubMed citation Europe PMC
Last Modified
01 June 2015