SCS-C007246

aspernigrin C

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

Download: SDF SMILES

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

570.6 Da

Threshold ≤ 500

ALogP

3.60

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C32H30N2O8

Molecular Weight:

570.5980 Da

SMILES:

COc1cc([C@H](Cc2ccccc2)n2cc(C(=O)NC(=O)C[C@H](C)C(=O)O)c(=O)cc2Cc2ccccc2)oc(=O)c1

InChIKey:

                        FWBIJYAFBSWBPA-FNZWTVRRSA-N
                        
                    

InChI:

InChI=1S/C32H30N2O8/c1-20(32(39)40)13-29(36)33-31(38)25-19-34(23(16-27(25)35)14-21-9-5-3-6-10-21)26(15-22-11-7-4-8-12-22)28-17-24(41-2)18-30(37)42-28/h3-12,16-20,26H,13-15H2,1-2H3,(H,39,40)(H,33,36,38)/t20-,26-/m0/s1

Calculated Properties

ALogP:

3.600 lipophilicity

TPSA:

144.91 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (4 aromatic)

Chiral Centers:

Fsp³:

0.2188 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007246

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	4.3–5.1000000000000005 μM	10.1016/j.bmcl.2015.12.005 Bioorganic & Medicinal Chemistry Letters

Back to Compounds