SCS-C008057
asperfatsine D
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids
Class: Indole diketopiperazine alkaloids (L-Trp, L-Ala)
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.
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
512.1 Da
Threshold ≤ 500
ALogP
5.04
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C29H38ClN3O3
Molecular Weight:
512.0940 Da
SMILES:
C=CC(C)(C)c1[nH]c2c(C[C@H](O)C(C)(C)Cl)c(CC=C(C)C)ccc2c1/C=C1\NC(=O)[C@H](C)NC1=O
InChIKey:
CDMYDOYAFDHDSS-KNHMBXKSSA-N
InChI:
InChI=1S/C29H38ClN3O3/c1-9-28(5,6)25-21(14-22-27(36)31-17(4)26(35)32-22)19-13-12-18(11-10-16(2)3)20(24(19)33-25)15-23(34)29(7,8)30/h9-10,12-14,17,23,33-34H,1,11,15H2,2-8H3,(H,31,36)(H,32,35)/b22-14-/t17-,23-/m0/s1
Calculated Properties
ALogP:
5.036 lipophilicity
TPSA:
94.22 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
3
Rotatable Bonds:
8
Ring Count:
3
(2 aromatic)
Chiral Centers:
2
Fsp³:
0.4483 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008057
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Peptide alkaloids
NPClassifier Class:
Indole diketopiperazine alkaloids (L-Trp, L-Ala)
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 |
| Anti-inflammatory | gene expression downregulation | Figure 5A and B | Pretreatment of different concentrations of 4 resulted in dose-dependent reductions in the expression of ICAM-1 and VCAM-1 (Figure 5A and B). | 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 |