SCS-C007283
6,8-dimethoxy-3-methylisocoumarin
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 terreus
(mangrove endophytic fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus terreus
South China Sea
DOI:
10.1016/s1875-5364(19)30017-2
· Chinese Journal of Natural Medicines
Drug-likeness (Lipinski Ro5)
Molecular Weight
222.2 Da
Threshold ≤ 500
ALogP
1.81
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C12H14O4
Molecular Weight:
222.2400 Da
SMILES:
COc1cc2c(c(OC)c1)C(=O)O[C@@H](C)C2
InChIKey:
XANBXQAFBJDNNB-ZETCQYMHSA-N
InChI:
InChI=1S/C12H14O4/c1-7-4-8-5-9(14-2)6-10(15-3)11(8)12(13)16-7/h5-7H,4H2,1-3H3/t7-/m0/s1
Calculated Properties
ALogP:
1.805 lipophilicity
TPSA:
44.76 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
4
Rotatable Bonds:
2
Ring Count:
2
(1 aromatic)
Chiral Centers:
1
Fsp³:
0.4167 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007283
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 |
|---|---|---|---|---|
| Antimycobacterial | inhibition rate | Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) | < 60.0 % | 10.1016/s1875-5364(19)30017-2 Chinese Journal of Natural Medicines |
| Antitumor | activity level | human glioma U87 cells | all these compounds (1?17) exhibited weak or no cytotoxic activities towards human glioma U87 cells at a concentration of 10 μmol·L?1 | 10.1016/s1875-5364(19)30017-2 Chinese Journal of Natural Medicines |
| Neuroprotective / Neuromodulatory | activity level | glutamate-induced toxicity in HT22 cells | — Structured numeric value is not available in this record; see the primary reference. | 10.1016/s1875-5364(19)30017-2 Chinese Journal of Natural Medicines |