SCS-C000263

versiquinazoline Q

Pathway: Alkaloids | Amino acids and Peptides Superclass: Peptide 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.

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

355.4 Da

Threshold ≤ 500

ALogP

1.80

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C19H21N3O4

Molecular Weight:

355.4000 Da

SMILES:

C=CC(C)(C)[C@@]12C=C(O)C(=O)N3[C@@H](C)C(=O)N[C@]31N(O)c1ccccc12

InChIKey:

                        UNSBPRMVTRXQEW-BKOMCJNNSA-N
                        
                    

InChI:

InChI=1S/C19H21N3O4/c1-5-17(3,4)18-10-14(23)16(25)21-11(2)15(24)20-19(18,21)22(26)13-9-7-6-8-12(13)18/h5-11,23,26H,1H2,2-4H3,(H,20,24)/t11-,18-,19-/m0/s1

Calculated Properties

ALogP:

1.802 lipophilicity

TPSA:

93.11 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (1 aromatic)

Chiral Centers:

Fsp³:

0.3684 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000263

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

N/A

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

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