SCS-C006072
10-phenyl-[12]-cytochalasin Z16
Pathway: Alkaloids
Superclass: Pseudoalkaloids
Class: Cytochalasan alkaloids
Chemical Structure
![Structure of 10-phenyl-[12]-cytochalasin Z16](/scsmarinenp/static/images/structures/SCS-C006072.png)
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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
463.6 Da
Threshold ≤ 500
ALogP
3.31
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C28H33NO5
Molecular Weight:
463.5740 Da
SMILES:
C=C1[C@@H](O)C2/C=C/C[C@H](C)C(=O)/C(C)=C/CC(=O)O[C@]23C(=O)N[C@@H](Cc2ccccc2)[C@@H]3[C@@H]1C
InChIKey:
XIWMGCLILBQGSO-WLOFJACYSA-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/h5-8,10-13,16,18,21-22,24,26,32H,4,9,14-15H2,1-3H3,(H,29,33)/b12-8+,17-13+/t16-,18+,21?,22-,24-,26+,28+/m0/s1
Calculated Properties
ALogP:
3.310 lipophilicity
TPSA:
92.70 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
5
Rotatable Bonds:
2
Ring Count:
4
(1 aromatic)
Chiral Centers:
7
Fsp³:
0.4643 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006072
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 | IC50 | small cell lung cancer cell line H446; small cell lung cancer cell line H1048 | 0.044–1.61 μM | 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 |