SCS-C006074
cytochalasin Z13
Pathway: Alkaloids
Superclass: Pseudoalkaloids
Class: Cytochalasan alkaloids
Chemical Structure
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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.
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
427.5 Da
Threshold ≤ 500
ALogP
1.93
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C25H33NO5
Molecular Weight:
427.5410 Da
SMILES:
CC1=C(C)[C@H]2[C@H](Cc3ccccc3)NC(=O)[C@@]2(O)[C@@H](/C=C/C[C@H](C)C(=O)[C@H](C)O)[C@@H]1O
InChIKey:
DCWOIJNXHXDCKT-YJFGZGKKSA-N
InChI:
InChI=1S/C25H33NO5/c1-14(22(28)17(4)27)9-8-12-19-23(29)16(3)15(2)21-20(26-24(30)25(19,21)31)13-18-10-6-5-7-11-18/h5-8,10-12,14,17,19-21,23,27,29,31H,9,13H2,1-4H3,(H,26,30)/b12-8+/t14-,17-,19-,20-,21-,23+,25+/m0/s1
Calculated Properties
ALogP:
1.934 lipophilicity
TPSA:
106.86 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
5
Rotatable Bonds:
7
Ring Count:
3
(1 aromatic)
Chiral Centers:
7
Fsp³:
0.5200 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006074
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Pseudoalkaloids
NPClassifier Class:
Cytochalasan alkaloids
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 |
|---|---|---|---|---|
| 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 against the small cell lung cancer cell lines H446 and H1048. [...] compounds 5, 7, and 8 showed significant cytotoxicity | 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 |