SCS-C000261
versiquinazoline O
Pathway: Alkaloids
Superclass: Anthranilic acid alkaloids
Class: Quinazoline 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
Aspergillus versicolor
(coral-associated fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus versicolor
South China Sea
DOI:
10.1039/c8ra06854b
· RSC Advances
Drug-likeness (Lipinski Ro5)
Molecular Weight
487.5 Da
Threshold ≤ 500
ALogP
2.10
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C27H29N5O4
Molecular Weight:
487.5000 Da
SMILES:
CCC(C)[C@@H]1N[C@@H]2N(C1=O)c1ccccc1[C@]2(O)C[C@@H]1C(=O)N[C@H](C)c2nc3ccccc3c(=O)n21
InChIKey:
SKFGYWJEITZBTI-YHRZVBOISA-N
InChI:
InChI=1S/C27H29N5O4/c1-4-14(2)21-25(35)32-19-12-8-6-10-17(19)27(36,26(32)30-21)13-20-23(33)28-15(3)22-29-18-11-7-5-9-16(18)24(34)31(20)22/h5-12,14-15,20-21,26,30,36H,4,13H2,1-3H3,(H,28,33)/t14?,15-,20-,21+,26-,27-/m1/s1
Calculated Properties
ALogP:
2.097 lipophilicity
TPSA:
116.56 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
7
Rotatable Bonds:
4
Ring Count:
6
(3 aromatic)
Chiral Centers:
6
Fsp³:
0.4074 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000261
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Anthranilic acid alkaloids
NPClassifier Class:
Quinazoline 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 |
|---|---|---|---|---|
| Enzyme inhibition | IC50 | TrxR | 13.0 μM | 10.1039/c8ra06854b RSC Advances |
| Antitumor | IC50 | A549 cell line | > 10.0 μM | 10.1039/c8ra06854b RSC Advances |