SCS-C007245

aspernigrin B

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

456.5 Da

Threshold ≤ 500

ALogP

3.33

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H24N2O5

Molecular Weight:

456.4980 Da

SMILES:

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

InChIKey:

                        CPVCVIXCXKPURM-QHCPKHFHSA-N
                        
                    

InChI:

InChI=1S/C27H24N2O5/c1-33-21-15-25(34-26(31)16-21)23(13-19-10-6-3-7-11-19)29-17-22(27(28)32)24(30)14-20(29)12-18-8-4-2-5-9-18/h2-11,14-17,23H,12-13H2,1H3,(H2,28,32)/t23-/m0/s1

Calculated Properties

ALogP:

3.332 lipophilicity

TPSA:

104.53 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (4 aromatic)

Chiral Centers:

Fsp³:

0.1481 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007245

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	inhibition	CCR5-tropic HIV-1 SF162 infection	— Structured numeric value is not available in this record; see the primary reference.	10.1016/j.bmcl.2015.12.005 Bioorganic & Medicinal Chemistry Letters

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