SCS-C002054
orlandin
Pathway: Shikimates and Phenylpropanoids
Superclass: Coumarins
Class: Simple coumarins
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
Aspergillus niger ASSB4
(alga)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus niger
South China Sea
DOI:
10.1007/s00044-020-02658-6
· Medicinal Chemistry Research
Drug-likeness (Lipinski Ro5)
Molecular Weight
410.4 Da
Threshold ≤ 500
ALogP
3.61
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
8
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H18O8
Molecular Weight:
410.4000 Da
SMILES:
COc1cc(=O)oc2c(-c3c(O)cc(C)c4c(OC)cc(=O)oc34)c(O)cc(C)c12
InChIKey:
SSGXAFNGBRRLQM-UHFFFAOYSA-N
InChI:
InChI=1S/C22H18O8/c1-9-5-11(23)19(21-17(9)13(27-3)7-15(25)29-21)20-12(24)6-10(2)18-14(28-4)8-16(26)30-22(18)20/h5-8,23-24H,1-4H3
Calculated Properties
ALogP:
3.612 lipophilicity
TPSA:
119.34 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
8
Rotatable Bonds:
3
Ring Count:
4
(4 aromatic)
Chiral Centers:
0
Fsp³:
0.1818 fraction sp³ carbon
Database Information
Compound ID:
SCS-C002054
NPClassifier Pathway:
Shikimates and Phenylpropanoids
NPClassifier Superclass:
Coumarins
NPClassifier Class:
Simple coumarins
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 | inhibition_percent | PC-3 cells | 25.0 % | 10.1007/s00044-020-02658-6 Medicinal Chemistry Research |