SCS-C001731

notoamide C

Pathway: Alkaloids | Amino acids and Peptides Superclass: Peptide alkaloids Class: Indole diketopiperazine alkaloids (L-Trp, L-Pro)

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Chemical Structure

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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.

Download: SDF SMILES

Source Information

Aspergillus westerdijkiae DFFSCS013 (NA)

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

South China Sea

DOI: 10.1007/s10295-014-1412-9 · Journal of Industrial Microbiology and Biotechnology

Drug-likeness (Lipinski Ro5)

Molecular Weight

449.5 Da

Threshold ≤ 500

ALogP

3.15

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C26H31N3O4

Molecular Weight:

449.5000 Da

SMILES:

C=CC(C)(C)[C@]1(C[C@@H]2NC(=O)[C@@H]3CCCN3C2=O)C(=O)Nc2c1ccc1c2C=CC(C)(C)O1

InChIKey:

                        KNFZHRYXLWKRSU-XWXLMPLOSA-N
                        
                    

InChI:

InChI=1S/C26H31N3O4/c1-6-24(2,3)26(14-17-22(31)29-13-7-8-18(29)21(30)27-17)16-9-10-19-15(20(16)28-23(26)32)11-12-25(4,5)33-19/h6,9-12,17-18H,1,7-8,13-14H2,2-5H3,(H,27,30)(H,28,32)/t17-,18-,26-/m0/s1

Calculated Properties

ALogP:

3.152 lipophilicity

TPSA:

87.74 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (1 aromatic)

Chiral Centers:

Fsp³:

0.5000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001731

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

Indole diketopiperazine alkaloids (L-Trp, L-Pro)

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
Antifouling	EC50	Bugula neritina larvae	9.85 μg/mL	10.1007/s10295-014-1412-9 Journal of Industrial Microbiology and Biotechnology
Antifouling	LC50	Bugula neritina larvae	> 200.0 μg/mL	10.1007/s10295-014-1412-9 Journal of Industrial Microbiology and Biotechnology

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