SCS-C007043
phenylahistin
Pathway: Alkaloids
Superclass: Histidine alkaloids
Class: Imidazole alkaloids
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
Phomopsis sp. SYSUQYP-23
(fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Diaporthales
Family
Diaporthaceae
Genus
Phomopsis
Species
NA
South China Sea
DOI:
10.1016/j.bioorg.2020.103712
· Bioorganic Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
350.4 Da
Threshold ≤ 500
ALogP
2.07
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C20H22N4O2
Molecular Weight:
350.4220 Da
SMILES:
C=CC(C)(C)c1[nH]cnc1/C=C1\NC(=O)[C@H](Cc2ccccc2)NC1=O
InChIKey:
GWMHBVLPNWHWGW-CNYBTUBUSA-N
InChI:
InChI=1S/C20H22N4O2/c1-4-20(2,3)17-14(21-12-22-17)11-16-19(26)23-15(18(25)24-16)10-13-8-6-5-7-9-13/h4-9,11-12,15H,1,10H2,2-3H3,(H,21,22)(H,23,26)(H,24,25)/b16-11-/t15-/m0/s1
Calculated Properties
ALogP:
2.071 lipophilicity
TPSA:
86.88 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
3
Rotatable Bonds:
5
Ring Count:
3
(2 aromatic)
Chiral Centers:
1
Fsp³:
0.2500 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007043
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Histidine alkaloids
NPClassifier Class:
Imidazole alkaloids
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 |
|---|---|---|---|---|
| Anti-inflammatory | IC50 | Nitric oxide (NO) production | 25.0 μM | 10.1016/j.bioorg.2020.103712 Bioorganic Chemistry |