SCS-C006819
penicillenol B1
Pathway: Amino acids and Peptides | Polyketides
Superclass: Linear polyketides
Class: 3-acyl tetramic acids
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
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
1
Threshold ≤ 5
H-Bond Acceptors
3
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-SDQBBNPISA-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 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
7
Ring Count:
1
(0 aromatic)
Chiral Centers:
1
Fsp³:
0.6250 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006819
NPClassifier Pathway:
Amino acids and Peptides
Polyketides
NPClassifier Superclass:
Linear polyketides
NPClassifier Class:
3-acyl tetramic acids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
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 | 8.0 μM (2.2 μg ml-1) | 10.1038/ja.2017.45 The Journal of Antibiotics |
| Antifungal | BIC80 | Candida albicans | 100.0 μg ml-1 | 10.1038/ja.2017.45 The Journal of Antibiotics |
| Antivirulence / Quorum sensing | inhibition rate | Candida albicans preformed biofilms | 62.0 % | 10.1038/ja.2017.45 The Journal of Antibiotics |
| Antifungal | — | Candida albicans | hyphal growth was modest in 25 μg ml-1 penicillenol A2 and 50 μg ml-1 penicillenol B1 | 10.1038/ja.2017.45 The Journal of Antibiotics |
| Other specified activity | transcript level reduction | HWP1, ALS1, ALS3, ECE1, SAP4 | — Structured numeric value is not available in this record; see the primary reference. | 10.1038/ja.2017.45 The Journal of Antibiotics |
| Antifungal | EPS inhibition | Candida albicans EPS | 31.0 % | 10.1038/ja.2017.45 The Journal of Antibiotics |
| Antifungal | Pz value | Candida albicans phospholipase | 0.79 | 10.1038/ja.2017.45 The Journal of Antibiotics |
| Antivirulence / Quorum sensing | — | Candida albicans biofilms | both penicillenols A2 and B1 might synergistically act with the antifungal agent AmB on C. albicans biofilm formation | 10.1038/ja.2017.45 The Journal of Antibiotics |