SCS-C000259

versiquinazoline M

Pathway: Alkaloids Superclass: Anthranilic acid alkaloids Class: Quinazoline alkaloids

Chemical Structure

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Download: SDF SMILES

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

445.4 Da

Threshold ≤ 500

ALogP

-0.29

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C23H19N5O5

Molecular Weight:

445.4000 Da

SMILES:

O=C1N[C@@H]2c3nc4ccccc4c(=O)n3[C@H]1C[C@]1(O)c3ccccc3N3C(=O)[C@H](CO)N2[C@H]31

InChIKey:

                        OSEDKWKVFUDTBD-FMQYXTRESA-N
                        
                    

InChI:

InChI=1S/C23H19N5O5/c29-10-16-21(32)28-14-8-4-2-6-12(14)23(33)9-15-19(30)25-18(27(16)22(23)28)17-24-13-7-3-1-5-11(13)20(31)26(15)17/h1-8,15-16,18,22,29,33H,9-10H2,(H,25,30)/t15-,16-,18-,22+,23-/m0/s1

Calculated Properties

ALogP:

-0.293 lipophilicity

TPSA:

128.00 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (3 aromatic)

Chiral Centers:

Fsp³:

0.3043 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000259

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Anthranilic acid alkaloids

NPClassifier Class:

Quinazoline alkaloids

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas

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	12.0 μM	10.1039/c8ra06854b RSC Advances
Antitumor	IC50	A549 cell line	> 10.0 μM	10.1039/c8ra06854b RSC Advances

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