SCS-C005974

(±)-pestalachloride D

Pathway: Polyketides | Terpenoids

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

Pestalotiopsis sp. ZJ-2009-7-6), isolated from Sarcophyton sp. (coral-associated fungus)

Original source name: Pestalotiopsis sp. (ZJ-2009-7-6), isolated from Sarcophyton sp.

Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Amphisphaeriales Family Sporocadaceae Genus Pestalotiopsis Species NA

South China Sea

DOI: 10.3390/md11041050 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

423.3 Da

Threshold ≤ 500

ALogP

5.01

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:

C21H20Cl2O5

Molecular Weight:

423.2920 Da

SMILES:

COc1c(Cl)c(C)c(Cl)c2c1[C@H]1c3c(C=O)c(O)cc(O)c3C[C@H]1C(C)(C)O2

InChIKey:

                        ANCGXXHYXGKUAF-IAQYHMDHSA-N
                        
                    

InChI:

InChI=1S/C21H20Cl2O5/c1-8-17(22)19(27-4)16-15-11(21(2,3)28-20(16)18(8)23)5-9-12(25)6-13(26)10(7-24)14(9)15/h6-7,11,15,25-26H,5H2,1-4H3/t11-,15-/m1/s1

Calculated Properties

ALogP:

5.009 lipophilicity

TPSA:

75.99 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (2 aromatic)

Chiral Centers:

Fsp³:

0.3810 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005974

NPClassifier Pathway:

Polyketides Terpenoids

NPClassifier Superclass:

N/A

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
Antibacterial	MIC	Escherichia coli	5.0 μM	10.3390/md11041050 Marine Drugs
Antibacterial	MIC	Vibrio anguillarum	10.0 μM	10.3390/md11041050 Marine Drugs
Antibacterial	MIC	Vibrio parahaemolyticus	20.0 μM	10.3390/md11041050 Marine Drugs
Toxicity	—	Danio rerio embryos	compound 1 was inactive at a concentration of 50 μg/mL, while 2 led to abnormal growth effects in several aspects of the embryonic development.	10.3390/md11041050 Marine Drugs

Back to Compounds