SCS-C008059

breynivosine A

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

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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 sp. SCSIO 41034 (coral-derived fungus)

Original source name: Aspergillus sp. SCSIO41034 (isolated from an unidentified sponge species)

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

South China Sea

DOI: 10.1021/acs.jnatprod.5c00077 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

493.6 Da

Threshold ≤ 500

ALogP

3.79

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C29H39N3O4

Molecular Weight:

493.6480 Da

SMILES:

C=CC(C)(C)c1[nH]c2c(C[C@H](O)C(C)(C)O)c(CC=C(C)C)ccc2c1/C=C1\NC(=O)[C@H](C)NC1=O

InChIKey:

                        PQKTYRJLSIDFMW-KNHMBXKSSA-N
                        
                    

InChI:

InChI=1S/C29H39N3O4/c1-9-28(5,6)25-21(14-22-27(35)30-17(4)26(34)31-22)19-13-12-18(11-10-16(2)3)20(24(19)32-25)15-23(33)29(7,8)36/h9-10,12-14,17,23,32-33,36H,1,11,15H2,2-8H3,(H,30,35)(H,31,34)/b22-14-/t17-,23-/m0/s1

Calculated Properties

ALogP:

3.790 lipophilicity

TPSA:

114.45 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.4483 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008059

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

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

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	inhibition effect	Monocyte adhesion to endothelial cells	— Structured numeric value is not available in this record; see the primary reference.	10.1021/acs.jnatprod.5c00077 Journal of Natural Products
Antiviral	inactivity	dengue virus; Zika virus	However, all tested compounds were inactive to both viruses and cancer cell lines at a concentration of 20.0 μM.	10.1021/acs.jnatprod.5c00077 Journal of Natural Products
Antitumor	inactivity	A549 cancer cells	However, all tested compounds were inactive to both viruses and cancer cell lines at a concentration of 20.0 μM.	10.1021/acs.jnatprod.5c00077 Journal of Natural Products
Antitumor	—	Human umbilical vein endothelial cells (HUVECs)	whereas the other compounds showed no significant cytotoxicity at a concentration of 20.0 μM (Figure 4A).	10.1021/acs.jnatprod.5c00077 Journal of Natural Products

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