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CHEBI:67731 - scalaradial

ChEBI IDCHEBI:67731
ChEBI Namescalaradial
Stars
DefinitionA scalarane sesterterpenoid with formula C27H40O4. It is a natural product found in the marine sponges Spongia officinalis and Cacospongia mollior, and exhibits anti-inflammatory activity.
Last Modified14 October 2021
DownloadsMolfile
FormulaC27H40O4
Net Charge0
Average Mass428.613
Monoisotopic Mass428.29266
SMILES[H]C(=O)C1=CC[C@]2([H])[C@@](C)([C@H]1C([H])=O)[C@@H](OC(C)=O)C[C@@]1([H])[C@@]2(C)CC[C@@]2([H])C(C)(C)CCC[C@]12C
InChIInChI=1S/C27H40O4/c1-17(30)31-23-14-22-25(4)12-7-11-24(2,3)20(25)10-13-26(22,5)21-9-8-18(15-28)19(16-29)27(21,23)6/h8,15-16,19-23H,7,9-14H2,1-6H3/t19-,20-,21-,22+,23-,25-,26-,27+/m0/s1
InChIKeyADWFEADZGIHPDE-QGERINELSA-N
Species of MetaboliteComponentSourceComments
Spongia officinalis (ncbitaxon:252964) - PubMed (21548580) Diethyl ether soluble portion of acetone extract of chopped, frozen sponge.
Cacospongia mollior (ncbitaxon:1162743) - DOI (10.1007/BF01938315)
Glossodoris rufomarginata (ncbitaxon:508147) - PubMed (15620263)
Hypomontagnella monticulosa (ncbitaxon:2487000) - PubMed (33665446) Strain: Zg15SU
Roles Classification
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 3.1.1.4 (phospholipase A2) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of phospholipase A2 (EC 3.1.1.4).
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
TRP channel blocker  An agent that inhibits the passage of cations through the transient receptor potential (TRP) channels.
animal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
scalaradial (CHEBI:67731) has role animal metabolite (CHEBI:75767)
scalaradial (CHEBI:67731) has role anti-inflammatory agent (CHEBI:67079)
scalaradial (CHEBI:67731) has role apoptosis inducer (CHEBI:68495)
scalaradial (CHEBI:67731) has role EC 3.1.1.4 (phospholipase A2) inhibitor (CHEBI:50469)
scalaradial (CHEBI:67731) has role marine metabolite (CHEBI:76507)
scalaradial (CHEBI:67731) has role TRP channel blocker (CHEBI:139361)
scalaradial (CHEBI:67731) is a acetate ester (CHEBI:47622)
scalaradial (CHEBI:67731) is a carbotetracyclic compound (CHEBI:177332)
scalaradial (CHEBI:67731) is a dialdehyde (CHEBI:38124)
scalaradial (CHEBI:67731) is a enal (CHEBI:51688)
scalaradial (CHEBI:67731) is a scalarane sesterterpenoid (CHEBI:59370)
IUPAC Name 
(4aS,4bR,6S,6aS,7R,10aS,10bR,12aS)-7,8-diformyl-1,1,4a,6a,10b-pentamethyl-1,2,3,4,4a,4b,5,6,6a,7,10,10a,10b,11,12,12a-hexadecahydrochrysen-6-yl acetate
Synonym  Source
(+)-scalaradialKNApSAcK
Manual XrefsDatabases
C00043907KNApSAcK
10272825ChemSpider
Registry NumbersSources
CAS:53527-28-9ChemIDplus
Citations