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CHEBI:5171 - friedelin

ChEBI IDCHEBI:5171
ChEBI Namefriedelin
Stars
DefinitionA 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.
Last Modified1 June 2015
DownloadsMolfile
FormulaC30H50O
Net Charge0
Average Mass426.729
Monoisotopic Mass426.38617
SMILES[H][C@]12CC[C@]3(C)[C@@H](C)C(=O)CC[C@@]3([H])[C@]1(C)CC[C@@]1(C)[C@]3([H])CC(C)(C)CC[C@]3(C)CC[C@]21C
InChIInChI=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
InChIKeyOFMXGFHWLZPCFL-SVRPQWSVSA-N
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
Applications:
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.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
anti-inflammatory drug  A substance that reduces or suppresses inflammation.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
friedelan-3-oneChemIDplus
D:A-friedooleanan-3-oneChemIDplus
friedelineChemIDplus
(−)-friedelinChEBI
UniProt Name  Source
friedelinUniProt
Manual XrefsDatabases
C08626KEGG COMPOUND
CPD-13047MetaCyc
WO2009072916Patent
C00003747KNApSAcK
Registry NumbersSources
CAS:559-74-0KEGG COMPOUND
CAS:559-74-0ChemIDplus
Citations