SCS-C000349
ochratoxin A
Pathway: Shikimates and Phenylpropanoids
Superclass: Coumarins
Class: Isocoumarins
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 sp.
(coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
NA
South China Sea
DOI:
10.1016/j.fct.2012.11.037
· Food and Chemical Toxicology
Drug-likeness (Lipinski Ro5)
Molecular Weight
403.8 Da
Threshold ≤ 500
ALogP
2.57
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C20H18ClNO6
Molecular Weight:
403.8000 Da
SMILES:
C[C@@H]1Cc2c(Cl)cc(C(=O)N[C@@H](Cc3ccccc3)C(=O)O)c(O)c2C(=O)O1
InChIKey:
RWQKHEORZBHNRI-BMIGLBTASA-N
InChI:
InChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1
Calculated Properties
ALogP:
2.573 lipophilicity
TPSA:
112.93 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
5
Rotatable Bonds:
5
Ring Count:
3
(2 aromatic)
Chiral Centers:
2
Fsp³:
0.2500 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000349
NPClassifier Pathway:
Shikimates and Phenylpropanoids
NPClassifier Superclass:
Coumarins
NPClassifier Class:
Isocoumarins
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 |
|---|---|---|---|---|
| Toxicity | LC50 | Artemia salina | 13.74 μM | 10.1016/j.fct.2012.11.037 Food and Chemical Toxicology |