SCS-C001646

11-epi-Sinulariolide acetate

Pathway: Terpenoids Superclass: Diterpenoids Class: Cembrane diterpenoids

Chemical Structure

Structure of 11-epi-Sinulariolide acetate

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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

Sinularia flexibilis (soft coral)

Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species Sinularia flexibilis

Xidao Island

DOI: 10.1016/j.bmcl.2018.12.004 · Bioorganic & Medicinal Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

464.6 Da

Threshold ≤ 500

ALogP

4.56

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C26H40O7

Molecular Weight:

464.5990 Da

SMILES:

C=C(C(=O)OC(C)=O)[C@H]1CC[C@](C)(O)[C@H](OC(C)=O)CCC/C=C(\C)CC[C@H]2O[C@]2(C)CC1

InChIKey:

                        BJOQPZWFPVECBV-KNEHUMPZSA-N
                        
                    

InChI:

InChI=1S/C26H40O7/c1-17-9-7-8-10-22(31-19(3)27)25(5,30)15-13-21(18(2)24(29)32-20(4)28)14-16-26(6)23(33-26)12-11-17/h9,21-23,30H,2,7-8,10-16H2,1,3-6H3/b17-9+/t21-,22+,23+,25-,26+/m0/s1

Calculated Properties

ALogP:

4.559 lipophilicity

TPSA:

102.43 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (0 aromatic)

Chiral Centers:

Fsp³:

0.7308 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001646

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	IC50	TNF-α	2.7 μM	10.1016/j.bmcl.2018.12.004 Bioorganic & Medicinal Chemistry
Antitumor	IC50	HT-29, SNU-398, Capan-1	24.9–32.6 μM	10.1016/j.bmcl.2018.12.004 Bioorganic & Medicinal Chemistry

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