SCS-C007247

aspernigrin D

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

568.6 Da

Threshold ≤ 500

ALogP

4.10

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C33H32N2O7

Molecular Weight:

568.6260 Da

SMILES:

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

InChIKey:

                        FRYXMHAYTMRKBA-KMRXNPHXSA-N
                        
                    

InChI:

InChI=1S/C33H32N2O7/c1-21(22(2)36)14-31(38)34-33(40)27-20-35(25(17-29(27)37)15-23-10-6-4-7-11-23)28(16-24-12-8-5-9-13-24)30-18-26(41-3)19-32(39)42-30/h4-13,17-21,28H,14-16H2,1-3H3,(H,34,38,40)/t21-,28-/m0/s1

Calculated Properties

ALogP:

4.105 lipophilicity

TPSA:

124.68 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (4 aromatic)

Chiral Centers:

Fsp³:

0.2424 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007247

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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