SCS-C007470
arenarialin D
Pathway: Terpenoids
Superclass: Meroterpenoids
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
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
302.4 Da
Threshold ≤ 500
ALogP
3.06
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C18H22O4
Molecular Weight:
302.3700 Da
SMILES:
C[C@H]1CC[C@]2(C)OC(=O)[C@@H]3Oc4ccc(O)cc4C[C@@]1(C)[C@H]32
InChIKey:
QANUTESGUDRDSZ-JNRNSOEHSA-N
InChI:
InChI=1S/C18H22O4/c1-10-6-7-18(3)15-14(16(20)22-18)21-13-5-4-12(19)8-11(13)9-17(10,15)2/h4-5,8,10,14-15,19H,6-7,9H2,1-3H3/t10-,14+,15-,17+,18-/m0/s1
Calculated Properties
ALogP:
3.064 lipophilicity
TPSA:
55.76 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
4
Rotatable Bonds:
0
Ring Count:
4
(1 aromatic)
Chiral Centers:
5
Fsp³:
0.6111 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007470
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
N/A
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
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 |
| Anti-inflammatory | downregulation | p-NF-κB p65, P<0.05 | — Structured numeric value is not available in this record; see the primary reference. | 10.1021/acs.jnatprod.3c01239 Journal of Natural Products |