SCS-C008306

sinusiaesin A

Pathway: Terpenoids Superclass: Diterpenoids Class: Cembrane diterpenoids

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.

Download: SDF SMILES

Source Information

Sinularia siaesensis (soft coral)

Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order NA Family NA Genus NA Species NA

South China Sea

DOI: 10.1021/acs.orglett.1c01601 · Organic Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight

380.5 Da

Threshold ≤ 500

ALogP

3.95

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H36O5

Molecular Weight:

380.5250 Da

SMILES:

C=C(C(=O)OC)[C@@H]1CC[C@@](C)(OC)[C@@H](O)CC/C(C)=C/CC[C@]2(C)O[C@H]2C1

InChIKey:

                        FFKOYVQMULTKOB-MCMGSFFUSA-N
                        
                    

InChI:

InChI=1S/C22H36O5/c1-15-8-7-12-22(4)19(27-22)14-17(16(2)20(24)25-5)11-13-21(3,26-6)18(23)10-9-15/h8,17-19,23H,2,7,9-14H2,1,3-6H3/b15-8+/t17-,18+,19+,21-,22+/m1/s1

Calculated Properties

ALogP:

3.946 lipophilicity

TPSA:

68.29 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (0 aromatic)

Chiral Centers:

Fsp³:

0.7727 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008306

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Diterpenoids

NPClassifier Class:

Cembrane diterpenoids

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	inhibitory activity	LPS-induced inflammation	20.0 μM	10.1021/acs.orglett.1c01601 Organic Letters
Anti-inflammatory	inhibitory activity	pro-inflammatory cytokines IL-6 and IL-1β mRNA expression	20.0 μM	10.1021/acs.orglett.1c01601 Organic Letters

Back to Compounds