SCS-C007471

arenarialin E

Pathway: Terpenoids Superclass: Meroterpenoids

Chemical Structure

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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.

Download: SDF SMILES

Source Information

Dysidea arenaria (NA)

Kingdom Metazoa Phylum Porifera Class Demospongiae Order Dictyoceratida Family Dysideidae Genus Dysidea Species Dysidea arenaria

South China Sea · 15 m

DOI: 10.1021/acs.jnatprod.3c01239 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

326.4 Da

Threshold ≤ 500

ALogP

4.28

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C21H26O3

Molecular Weight:

326.4360 Da

SMILES:

CC1=CC(=O)[C@@H]2Oc3ccc(O)cc3C[C@]3(C)[C@@H](C)CC[C@@]1(C)[C@@H]23

InChIKey:

                        FVFDUMXWYVCGFB-NWXLSTKKSA-N
                        
                    

InChI:

InChI=1S/C21H26O3/c1-12-7-8-20(3)13(2)9-16(23)18-19(20)21(12,4)11-14-10-15(22)5-6-17(14)24-18/h5-6,9-10,12,18-19,22H,7-8,11H2,1-4H3/t12-,18-,19+,20+,21+/m0/s1

Calculated Properties

ALogP:

4.283 lipophilicity

TPSA:

46.53 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (1 aromatic)

Chiral Centers:

Fsp³:

0.5714 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007471

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Meroterpenoids

NPClassifier Class:

N/A

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas

Biological Activity Data

Activity values are displayed only when a quantitative or clearly reported result is available. Tested organisms, cell lines and molecular targets are shown under Target / model.

Activity	Assay	Target / model	Result	Reference
Anti-inflammatory	inhibition	TNF-α production	compounds 1, 2, 4, and 5 showed significant inhibitory activity against the production of TNF-α in LPS-induced RAW264.7 macrophages at 5, 10, and 20 μM concentrations	10.1021/acs.jnatprod.3c01239 Journal of Natural Products
Anti-inflammatory	inhibition	IL-6 production	arenarialins B (2) and D?F (4?6) exhibited potent inhibition on the production of IL-6 in a dose-dependent manner at concentrations of 2.5, 5, 10, and 20 μM	10.1021/acs.jnatprod.3c01239 Journal of Natural Products

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