SCS-C001458

Notoamide F

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 sclerotiorum GDST-2013-0501 (soft coral-derived fungus)

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

South China Sea

DOI: 10.3389/fmicb.2022.808532 · Frontiers in Microbiology

Drug-likeness (Lipinski Ro5)

Molecular Weight

461.6 Da

Threshold ≤ 500

ALogP

3.58

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H31N3O4

Molecular Weight:

461.6000 Da

SMILES:

CO[C@H]1c2c([nH]c3c4c(ccc23)OC(C)(C)C=C4)C(C)(C)[C@@H]2C[C@]34CCCN3C(=O)[C@]12NC4=O

InChIKey:

                        RWPUAUNPEMCSNR-CZQHCSHRSA-N
                        
                    

InChI:

InChI=1S/C27H31N3O4/c1-24(2)11-9-14-16(34-24)8-7-15-18-20(28-19(14)15)25(3,4)17-13-26-10-6-12-30(26)23(32)27(17,21(18)33-5)29-22(26)31/h7-9,11,17,21,28H,6,10,12-13H2,1-5H3,(H,29,31)/t17-,21-,26-,27+/m0/s1

Calculated Properties

ALogP:

3.580 lipophilicity

TPSA:

83.66 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (2 aromatic)

Chiral Centers:

Fsp³:

0.5556 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001458

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
Enzyme inhibition	—	DNA topoisomerase I	100.0 μM	10.3389/fmicb.2022.808532 Frontiers in Microbiology
Antibacterial	—	Staphylococcus epidermidis	12.5 μM	10.3389/fmicb.2022.808532 Frontiers in Microbiology

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