SCS-C000568
purpactin A
Pathway: Polyketides
Superclass: Aromatic polyketides
Class: Depsidones
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
Penicillium pinophilum
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium pinophilum
South China Sea
DOI:
10.1021/acs.jnatprod.5b00575
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
414.4 Da
Threshold ≤ 500
ALogP
4.82
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C23H26O7
Molecular Weight:
414.4000 Da
SMILES:
COc1c([C@H](CC(C)C)OC(C)=O)ccc2c1C(=O)OCc1cc(C)cc(O)c1O2
InChIKey:
NUYFKDBCHFKOBT-IBGZPJMESA-N
InChI:
InChI=1S/C23H26O7/c1-12(2)8-19(29-14(4)24)16-6-7-18-20(22(16)27-5)23(26)28-11-15-9-13(3)10-17(25)21(15)30-18/h6-7,9-10,12,19,25H,8,11H2,1-5H3/t19-/m0/s1
Calculated Properties
ALogP:
4.822 lipophilicity
TPSA:
91.29 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
7
Rotatable Bonds:
5
Ring Count:
3
(2 aromatic)
Chiral Centers:
1
Fsp³:
0.3913 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000568
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Aromatic polyketides
NPClassifier Class:
Depsidones
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 |
|---|---|---|---|---|
| Antitumor | EC50 | MCF7,H460,SF268 | 10.0 μg/mL | 10.1021/acs.jnatprod.5b00575 Journal of Natural Products |
| Antitumor | IC50 | MCF7,H460,SF268 | ≈ 2.0 μM | 10.1021/acs.jnatprod.5b00575 Journal of Natural Products |
| Antitumor | IC50 | MCF7,H460,SF268 | 20.5 μM | 10.1021/acs.jnatprod.5b00575 Journal of Natural Products |