SCS-C000260
versiquinazoline N
Pathway: Alkaloids
Superclass: Anthranilic acid alkaloids
Class: Quinazoline alkaloids
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 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
485.5 Da
Threshold ≤ 500
ALogP
2.25
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C27H27N5O4
Molecular Weight:
485.5000 Da
SMILES:
CCC(C)[C@@H]1N[C@@H]2N(C1=O)c1ccccc1[C@]21C[C@@H]2C(=O)N[C@](C)(O1)c1nc3ccccc3c(=O)n12
InChIKey:
PJWNQQLNZSOQAT-QCWPMIFTSA-N
InChI:
InChI=1S/C27H27N5O4/c1-4-14(2)20-23(35)31-18-12-8-6-10-16(18)27(25(31)29-20)13-19-21(33)30-26(3,36-27)24-28-17-11-7-5-9-15(17)22(34)32(19)24/h5-12,14,19-20,25,29H,4,13H2,1-3H3,(H,30,33)/t14?,19-,20+,25-,26-,27-/m1/s1
Calculated Properties
ALogP:
2.247 lipophilicity
TPSA:
105.56 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
7
Rotatable Bonds:
2
Ring Count:
8
(3 aromatic)
Chiral Centers:
6
Fsp³:
0.4074 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000260
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 |