SCS-C007973
euroticin B
Pathway: Polyketides
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
Eurotium sp.
(gorgonian-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Eurotium
Species
NA
South China Sea
· 158 m
· 17°29.804′N, 110°0.292′E
DOI:
10.1021/acs.joc.0c01407
· The Journal of Organic Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
298.4 Da
Threshold ≤ 500
ALogP
4.15
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C19H22O3
Molecular Weight:
298.3820 Da
SMILES:
C[C@H]1C=C[C@H]2CCc3c(O)cc4c(c3[C@H]2O1)OC(C)(C)C=C4
InChIKey:
YZMJMTPWSHCYBA-PRXAMGSTSA-N
InChI:
InChI=1S/C19H22O3/c1-11-4-5-12-6-7-14-15(20)10-13-8-9-19(2,3)22-18(13)16(14)17(12)21-11/h4-5,8-12,17,20H,6-7H2,1-3H3/t11-,12-,17-/m0/s1
Calculated Properties
ALogP:
4.155 lipophilicity
TPSA:
38.69 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
0
Ring Count:
4
(1 aromatic)
Chiral Centers:
3
Fsp³:
0.4737 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007973
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
N/A
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 |
|---|---|---|---|---|
| Antitumor | — | A549 human cancer cell lines | Compounds (+)-2 and (-)-2 displayed no cytotoxic activities against HepG-2, MCF-7, SF-268, and A549 cell lines at a concentration of 40 μM. | 10.1021/acs.joc.0c01407 The Journal of Organic Chemistry |
| Antioxidant | EC50 | DPPH radical | 35.6–39.4 μM | 10.1021/acs.joc.0c01407 The Journal of Organic Chemistry |
| Antioxidant | EC50 | DPPH radical | 20.5–22.700000000000003 μM | 10.1021/acs.joc.0c01407 The Journal of Organic Chemistry |
| Enzyme inhibition | — | α-glucosidase | They did not exhibit α-glucosidase or tyrosinase inhibitory activities. | 10.1021/acs.joc.0c01407 The Journal of Organic Chemistry |
| Enzyme inhibition | — | tyrosinase | They did not exhibit α-glucosidase or tyrosinase inhibitory activities. | 10.1021/acs.joc.0c01407 The Journal of Organic Chemistry |