SCS-C006820

penicillenol B2

Pathway: Amino acids and Peptides | Polyketides Superclass: Linear polyketides Class: 3-acyl tetramic acids

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 restrictus (NA)

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

South China Sea · 2326 m · 17°59'742' N, 111°48'092' E

DOI: 10.1038/ja.2017.45 · The Journal of Antibiotics

Drug-likeness (Lipinski Ro5)

Molecular Weight

279.4 Da

Threshold ≤ 500

ALogP

3.35

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C16H25NO3

Molecular Weight:

279.3800 Da

SMILES:

C/C=C1\C(O)=C(C(=O)C(C)CCCCCC)C(=O)N1C

InChIKey:

                        FRKQEEBAWRDYCO-WUXMJOGZSA-N
                        
                    

InChI:

InChI=1S/C16H25NO3/c1-5-7-8-9-10-11(3)14(18)13-15(19)12(6-2)17(4)16(13)20/h6,11,19H,5,7-10H2,1-4H3/b12-6+

Calculated Properties

ALogP:

3.350 lipophilicity

TPSA:

57.61 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

1 (0 aromatic)

Chiral Centers:

Fsp³:

0.6250 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006820

NPClassifier Pathway:

Amino acids and Peptides Polyketides

NPClassifier Superclass:

Linear polyketides

NPClassifier Class:

3-acyl tetramic acids

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
Antibacterial	MIC	Staphylococcus aureus	70.0 μM (19.4 μg ml-1)	10.1038/ja.2017.45 The Journal of Antibiotics
Antifungal	BIC80	Candida albicans	200.0 μg ml-1	10.1038/ja.2017.45 The Journal of Antibiotics

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