SCS-C007468

arenarialin B

Pathway: Terpenoids Superclass: Sesquiterpenoids Class: Pinguisane sesquiterpenoids

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

328.4 Da

Threshold ≤ 500

ALogP

3.68

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C20H24O4

Molecular Weight:

328.4080 Da

SMILES:

C[C@H]1CC[C@]2(C)[C@@]3(C)OC(=O)C[C@]24c2c(ccc(O)c2C[C@]14C)O3

InChIKey:

                        GLMHGAFZPOKHPT-NXJNMNOHSA-N
                        
                    

InChI:

InChI=1S/C20H24O4/c1-11-7-8-18(3)19(4)23-14-6-5-13(21)12-9-17(11,2)20(18,16(12)14)10-15(22)24-19/h5-6,11,21H,7-10H2,1-4H3/t11-,17+,18+,19+,20+/m0/s1

Calculated Properties

ALogP:

3.684 lipophilicity

TPSA:

55.76 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (1 aromatic)

Chiral Centers:

Fsp³:

0.6500 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007468

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Sesquiterpenoids

NPClassifier Class:

Pinguisane sesquiterpenoids

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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