SCS-C000290
aflaquinolone A
Pathway: Alkaloids
Superclass: Tryptophan alkaloids | Anthranilic acid alkaloids
Class: Quinoline alkaloids
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
Scopulariopsis sp.
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Microascales
Family
Microascaceae
Genus
Scopulariopsis
Species
NA
South China Sea
DOI:
10.1007/s10126-015-9628-x
· Bioscience, Biotechnology, and Biochemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
435.5 Da
Threshold ≤ 500
ALogP
4.00
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C26H29NO5
Molecular Weight:
435.5000 Da
SMILES:
CO[C@@H]1C(=O)Nc2ccc(/C=C/[C@]3(C)CCC(=O)[C@@H](C)C3)c(O)c2[C@@]1(O)c1ccccc1
InChIKey:
QWVOGENNJWSIPL-KRLQRQCXSA-N
InChI:
InChI=1S/C26H29NO5/c1-16-15-25(2,14-12-20(16)28)13-11-17-9-10-19-21(22(17)29)26(31,18-7-5-4-6-8-18)23(32-3)24(30)27-19/h4-11,13,16,23,29,31H,12,14-15H2,1-3H3,(H,27,30)/b13-11+/t16-,23+,25+,26-/m0/s1
Calculated Properties
ALogP:
4.004 lipophilicity
TPSA:
95.86 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
5
Rotatable Bonds:
4
Ring Count:
4
(2 aromatic)
Chiral Centers:
4
Fsp³:
0.3846 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000290
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Tryptophan alkaloids
Anthranilic acid alkaloids
NPClassifier Class:
Quinoline 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 |
|---|---|---|---|---|
| Antifouling | EC50 | Balanus amphitrite cyprids,Artemia salina | 2.8 nM | 10.1007/s10126-015-9628-x Bioscience, Biotechnology, and Biochemistry |
| Antifouling | LD50 | Balanus amphitrite cyprids,Artemia salina | 5.5 μM | 10.1007/s10126-015-9628-x Bioscience, Biotechnology, and Biochemistry |