CHEBI:67731 - scalaradial

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ChEBI Name scalaradial
ChEBI ID CHEBI:67731
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H40O4
Net Charge 0
Average Mass 428.613
Monoisotopic Mass 428.29266
InChI InChI=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
InChIKey ADWFEADZGIHPDE-QGERINELSA-N
SMILES [H]C(=O)[C@H]1C(=CC[C@@]2([H])[C@]3(C)CC[C@@]4([H])C(C)(C)CCC[C@]4(C)[C@@]3([H])C[C@H](OC(C)=O)[C@]12C)C([H])=O
Metabolite of Species Details
Cacospongia mollior (NCBI:txid1162743) See: DOI
Hypomontagnella monticulosa (NCBI:txid2487000) of strain Zg15SU See: PubMed
Spongia officinalis (NCBI:txid252964) Diethyl ether soluble portion of acetone extract of chopped, frozen sponge. See: PubMed
Glossodoris rufomarginata (NCBI:txid508147) See: PubMed
Roles Classification
Biological Role(s): marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
animal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
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).
TRP channel blocker
An agent that inhibits the passage of cations through the transient receptor potential (TRP) channels.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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
(+)-scalaradial KNApSAcK
Manual Xrefs Databases
10272825 ChemSpider
C00043907 KNApSAcK
View more database links
Registry Number Type Source
53527-28-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15620263 PubMed citation Europe PMC
15645482 PubMed citation Europe PMC
17579085 PubMed citation Europe PMC
17691073 PubMed citation Europe PMC
18000710 PubMed citation Europe PMC
1930288 PubMed citation Europe PMC
21548580 PubMed citation Europe PMC
22509253 PubMed citation Europe PMC
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24769547 PubMed citation Europe PMC
29019677 PubMed citation Europe PMC
33665446 PubMed citation Europe PMC
7575673 PubMed citation Europe PMC
8185681 PubMed citation Europe PMC
8688196 PubMed citation Europe PMC
9060998 PubMed citation Europe PMC
Last Modified
14 October 2021