SCS-C000561
pseurotin A
Pathway: Amino acids and Peptides | Polyketides
Superclass: Cyclic polyketides
Class: 3-Spirotetramic 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
Pseudallescheria boydii
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Microascales
Family
Microascaceae
Genus
Pseudallescheria
Species
Pseudallescheria boydii
South China Sea
DOI:
10.1021/acs.jnatprod.8b01053
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
431.4 Da
Threshold ≤ 500
ALogP
0.00
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
8
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H25NO8
Molecular Weight:
431.4000 Da
SMILES:
CC/C=C\[C@H](O)[C@H](O)C1=C(C)C(=O)[C@]2(O1)C(=O)N[C@@](OC)(C(=O)c1ccccc1)[C@@H]2O
InChIKey:
SLYDIPAXCVVRNY-UOWMTANKSA-N
InChI:
InChI=1S/C22H25NO8/c1-4-5-11-14(24)15(25)16-12(2)17(26)21(31-16)19(28)22(30-3,23-20(21)29)18(27)13-9-7-6-8-10-13/h5-11,14-15,19,24-25,28H,4H2,1-3H3,(H,23,29)/b11-5-/t14-,15-,19+,21+,22+/m0/s1
Calculated Properties
ALogP:
0.003 lipophilicity
TPSA:
142.39 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
8
Rotatable Bonds:
7
Ring Count:
3
(1 aromatic)
Chiral Centers:
5
Fsp³:
0.4091 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000561
NPClassifier Pathway:
Amino acids and Peptides
Polyketides
NPClassifier Superclass:
Cyclic polyketides
NPClassifier Class:
3-Spirotetramic 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 | IC50 | Erwinia carotovora,Pseudomonas syringae | 220.0 μg/mL | 10.1021/acs.jnatprod.8b01053 Journal of Natural Products |
| Antibacterial | MIC | Bacillus cereus,Shigella shiga | 64.0 μg/mL | 10.1021/acs.jnatprod.8b01053 Journal of Natural Products |
| Immunomodulatory / Anti-allergic | IC50 | IgE production | 3.6 μM | 10.1021/acs.jnatprod.8b01053 Journal of Natural Products |
| Bone metabolism / Osteoclast | IC50 | osteoclasts | 0.1 μM | 10.1021/acs.jnatprod.8b01053 Journal of Natural Products |