SCS-C001729

brevianamide F

Pathway: Alkaloids | Amino acids and Peptides Superclass: Peptide alkaloids | Small peptides Class: Dipeptides | 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

283.3 Da

Threshold ≤ 500

ALogP

1.20

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C16H17N3O2

Molecular Weight:

283.3200 Da

SMILES:

O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCC[C@@H]12

InChIKey:

                        RYFZBPVMVYTEKZ-KBPBESRZSA-N
                        
                    

InChI:

InChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1

Calculated Properties

ALogP:

1.200 lipophilicity

TPSA:

65.20 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (2 aromatic)

Chiral Centers:

Fsp³:

0.3750 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001729

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids Small peptides

NPClassifier Class:

Dipeptides 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	6.35 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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