SCS-C007244

aspernigrin A

Pathway: Alkaloids Superclass: Nicotinic acid alkaloids Class: Pyridine alkaloids

Chemical Structure

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Source Information

Aspergillus niger SCSIO Jcsw6F30 (alga)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus niger

South China Sea

DOI: 10.1016/j.bmcl.2015.12.005 · Bioorganic & Medicinal Chemistry Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight

228.3 Da

Threshold ≤ 500

ALogP

1.06

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C13H12N2O2

Molecular Weight:

228.2510 Da

SMILES:

NC(=O)c1c[nH]c(Cc2ccccc2)cc1=O

InChIKey:

                        RUUZDCZRFRLJFC-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C13H12N2O2/c14-13(17)11-8-15-10(7-12(11)16)6-9-4-2-1-3-5-9/h1-5,7-8H,6H2,(H2,14,17)(H,15,16)

Calculated Properties

ALogP:

1.065 lipophilicity

TPSA:

75.95 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (2 aromatic)

Chiral Centers:

Fsp³:

0.0769 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007244

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Nicotinic acid alkaloids

NPClassifier Class:

Pyridine 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
Antiviral	IC50	CCR5-tropic HIV-1 SF162 infection	61.8–104.6 μM	10.1016/j.bmcl.2015.12.005 Bioorganic & Medicinal Chemistry Letters

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