SCS-C008054
asperfatsine A
Pathway: Alkaloids | Amino acids and Peptides
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. SCSIO 41034
(coral-derived fungus)
Original source name: Aspergillus sp. SCSIO41034 (isolated from an unidentified sponge species)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
NA
South China Sea
DOI:
10.1021/acs.jnatprod.5c00077
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
605.8 Da
Threshold ≤ 500
ALogP
6.31
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C36H51N3O5
Molecular Weight:
605.8200 Da
SMILES:
C=CC(C)(C)c1[nH]c2c(C[C@H](OC(=O)CCCCCC)C(C)(C)O)c(CC=C(C)C)ccc2c1/C=C1\NC(=O)[C@H](C)NC1=O
InChIKey:
WUQAJMCMPVXTON-GSOWCHERSA-N
InChI:
InChI=1S/C36H51N3O5/c1-10-12-13-14-15-30(40)44-29(36(8,9)43)21-26-24(17-16-22(3)4)18-19-25-27(32(39-31(25)26)35(6,7)11-2)20-28-34(42)37-23(5)33(41)38-28/h11,16,18-20,23,29,39,43H,2,10,12-15,17,21H2,1,3-9H3,(H,37,42)(H,38,41)/b28-20-/t23-,29-/m0/s1
Calculated Properties
ALogP:
6.311 lipophilicity
TPSA:
120.52 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
5
Rotatable Bonds:
14
Ring Count:
3
(2 aromatic)
Chiral Centers:
2
Fsp³:
0.5278 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008054
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
N/A
NPClassifier Class:
N/A
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 |
|---|---|---|---|---|
| Anti-inflammatory | inhibition effect | Monocyte adhesion to endothelial cells | — Structured numeric value is not available in this record; see the primary reference. | 10.1021/acs.jnatprod.5c00077 Journal of Natural Products |
| Antiviral | inactivity | dengue virus; Zika virus | However, all tested compounds were inactive to both viruses and cancer cell lines at a concentration of 20.0 μM. | 10.1021/acs.jnatprod.5c00077 Journal of Natural Products |
| Antitumor | inactivity | A549 cancer cells | However, all tested compounds were inactive to both viruses and cancer cell lines at a concentration of 20.0 μM. | 10.1021/acs.jnatprod.5c00077 Journal of Natural Products |
| Antitumor | — | Human umbilical vein endothelial cells (HUVECs) | whereas the other compounds showed no significant cytotoxicity at a concentration of 20.0 μM (Figure 4A). | 10.1021/acs.jnatprod.5c00077 Journal of Natural Products |