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CHEBI:67731 - scalaradial

Default Structure
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
Cacospongia mollior (ncbitaxon:1162743) - DOI (10.1007/BF01938315)
Glossodoris rufomarginata (ncbitaxon:508147) - PubMed (15620263)
Hypomontagnella monticulosa (ncbitaxon:2487000) - PubMed (33665446) Strain: Zg15SU
Spongia officinalis (ncbitaxon:252964) - PubMed (21548580) Diethyl ether soluble portion of acetone extract of chopped, frozen sponge.
Roles Classification
Biological Roles:
TRP channel blocker  An agent that inhibits the passage of cations through the transient receptor potential (TRP) channels.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
animal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
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.
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
10272825ChemSpider
C00043907KNApSAcK
Registry NumbersSources
CAS:53527-28-9ChemIDplus
Citations