SCS-C006068

18Z-cytochalasin Z17

Pathway: Alkaloids Superclass: Pseudoalkaloids Class: Cytochalasan alkaloids

Chemical Structure

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Source Information

Aspergillus sp. (coral-derived fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species NA

South China Sea

DOI: 10.3390/molecules30224483 · Molecules

Drug-likeness (Lipinski Ro5)

Molecular Weight

463.6 Da

Threshold ≤ 500

ALogP

3.45

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C28H33NO5

Molecular Weight:

463.5740 Da

SMILES:

CC1=C(C)[C@H]2[C@H](Cc3ccccc3)NC(=O)[C@]23OC(=O)C/C=C(/C)C(=O)[C@@H](C)C/C=C/[C@H]3[C@@H]1O

InChIKey:

                        ZXLCFNNJGGXTCQ-LCPIHJEDSA-N
                        
                    

InChI:

InChI=1S/C28H33NO5/c1-16-9-8-12-21-26(32)19(4)18(3)24-22(15-20-10-6-5-7-11-20)29-27(33)28(21,24)34-23(30)14-13-17(2)25(16)31/h5-8,10-13,16,21-22,24,26,32H,9,14-15H2,1-4H3,(H,29,33)/b12-8+,17-13-/t16-,21-,22-,24-,26+,28+/m0/s1

Calculated Properties

ALogP:

3.454 lipophilicity

TPSA:

92.70 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (1 aromatic)

Chiral Centers:

Fsp³:

0.4643 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006068

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Pseudoalkaloids

NPClassifier Class:

Cytochalasan alkaloids

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
Antitumor	—	small cell lung cancer cell line H446; small cell lung cancer cell line H1048	All isolated compounds (1–10) were assessed for their cytotoxicity [...] compounds 3–8 exhibited varying degrees of inhibitory effect	10.3390/molecules30224483 Molecules
Antibacterial	—	Alternaria alternate, Curvularia australiensis, Rhizoctonia solani, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, Exiguobacterium profundum	Compounds 1–10 were also tested for their antimicrobial activities [...] none of those compounds showed observable activity with 50 μg per 6 mm disk.	10.3390/molecules30224483 Molecules

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