SCS-C000308

methyl 3,4,5-trimethoxy-2-(2-(nicotinamido) benzamido) benzoate

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

Chemical Structure

Structure of methyl 3,4,5-trimethoxy-2-(2-(nicotinamido) benzamido) benzoate

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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.

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Source Information

Aspergillus terreus (mangrove endophytic fungus)

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

South China Sea

DOI: 10.1016/j.bioorg.2018.06.029 · Bioorganic Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

465.5 Da

Threshold ≤ 500

ALogP

3.40

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C24H23N3O7

Molecular Weight:

465.4620 Da

SMILES:

COC(=O)c1cc(OC)c(OC)c(OC)c1NC(=O)c1ccccc1NC(=O)c1cccnc1

InChIKey:

                        DXZREYMSIRCHNS-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C24H23N3O7/c1-31-18-12-16(24(30)34-4)19(21(33-3)20(18)32-2)27-23(29)15-9-5-6-10-17(15)26-22(28)14-8-7-11-25-13-14/h5-13H,1-4H3,(H,26,28)(H,27,29)

Calculated Properties

ALogP:

3.399 lipophilicity

TPSA:

125.08 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (3 aromatic)

Chiral Centers:

Fsp³:

0.1667 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000308

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
Anti-inflammatory	IC50	NO production	5.48 μM	10.1016/j.bioorg.2018.06.029 Bioorganic Chemistry

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