SCS-C008061
arestrictin B
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids
Class: Indole diketopiperazine alkaloids (L-Trp, L-Ala)
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
461.6 Da
Threshold ≤ 500
ALogP
5.19
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C29H39N3O2
Molecular Weight:
461.6500 Da
SMILES:
C=CC(C)(C)c1[nH]c2c(CC=C(C)C)c(CC=C(C)C)ccc2c1C[C@@H]1NC(=O)[C@H](C)NC1=O
InChIKey:
RZKBCDQVIRHOQC-CYFREDJKSA-N
InChI:
InChI=1S/C29H39N3O2/c1-9-29(7,8)26-23(16-24-28(34)30-19(6)27(33)31-24)22-15-13-20(12-10-17(2)3)21(25(22)32-26)14-11-18(4)5/h9-11,13,15,19,24,32H,1,12,14,16H2,2-8H3,(H,30,34)(H,31,33)/t19-,24-/m0/s1
Calculated Properties
ALogP:
5.194 lipophilicity
TPSA:
73.99 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
2
Rotatable Bonds:
8
Ring Count:
3
(2 aromatic)
Chiral Centers:
2
Fsp³:
0.4483 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008061
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 | inactivity | 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 |