SCS-C000343
pestaloxazine A
Pathway: Alkaloids
Superclass: Lysine alkaloids
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.
Source Information
Pestalotiopsis sp.
(coral-associated fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Amphisphaeriales
Family
Sporocadaceae
Genus
Pestalotiopsis
Species
NA
South China Sea
DOI:
10.1021/acs.orglett.5b01995
· Organic Letters
Drug-likeness (Lipinski Ro5)
Molecular Weight
480.5 Da
Threshold ≤ 500
ALogP
-0.61
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:
C22H32N4O8
Molecular Weight:
480.5000 Da
SMILES:
C/C(=C\C(=O)N1CCC[C@@]2(NC(=O)[C@]3(CCCN(C(=O)/C=C(\C)CCO)O3)NC2=O)O1)CCO
InChIKey:
ULBZDTAPWSWKLY-UDVIYJLQSA-N
InChI:
InChI=1S/C22H32N4O8/c1-15(5-11-27)13-17(29)25-9-3-7-21(33-25)19(31)24-22(20(32)23-21)8-4-10-26(34-22)18(30)14-16(2)6-12-28/h13-14,27-28H,3-12H2,1-2H3,(H,23,32)(H,24,31)/b15-13+,16-14+/t21-,22-/m1/s1
Calculated Properties
ALogP:
-0.610 lipophilicity
TPSA:
157.74 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
8
Rotatable Bonds:
6
Ring Count:
3
(0 aromatic)
Chiral Centers:
2
Fsp³:
0.6364 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000343
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Lysine alkaloids
NPClassifier Class:
N/A
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 |
|---|---|---|---|---|
| Antiviral | IC50 | EV71 | 14.2 μM | 10.1021/acs.orglett.5b01995 Organic Letters |