SCS-C000228
tardioxopiperazine A
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids
Class: Indole diketopiperazine alkaloids (L-Trp, L-Ala)
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
Nigrospora oryzae
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Amphisphaeriales
Family
Apiosporaceae
Genus
Nigrospora
Species
Nigrospora oryzae
South China Sea
DOI:
10.1007/s10600-014-1189-0
· Chemistry of Natural Compounds
Drug-likeness (Lipinski Ro5)
Molecular Weight
393.5 Da
Threshold ≤ 500
ALogP
3.69
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C24H31N3O2
Molecular Weight:
393.5000 Da
SMILES:
C=CC(C)(C)c1[nH]c2ccc(CC=C(C)C)cc2c1C[C@@H]1NC(=O)[C@H](C)NC1=O
InChIKey:
WXGWEFVOPYZZTA-YWZLYKJASA-N
InChI:
InChI=1S/C24H31N3O2/c1-7-24(5,6)21-18(13-20-23(29)25-15(4)22(28)27-20)17-12-16(9-8-14(2)3)10-11-19(17)26-21/h7-8,10-12,15,20,26H,1,9,13H2,2-6H3,(H,25,29)(H,27,28)/t15-,20-/m0/s1
Calculated Properties
ALogP:
3.686 lipophilicity
TPSA:
73.99 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
2
Rotatable Bonds:
6
Ring Count:
3
(2 aromatic)
Chiral Centers:
2
Fsp³:
0.4167 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000228
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Peptide alkaloids
NPClassifier Class:
Indole diketopiperazine alkaloids (L-Trp, L-Ala)
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 | IC50 | Con A-induced | 4.5 μM | 10.1007/s10600-014-1189-0 Chemistry of Natural Compounds |
| Anti-inflammatory | IC50 | LPS-induced | 0.7 μM | 10.1007/s10600-014-1189-0 Chemistry of Natural Compounds |
| Antitumor | inhibition_percent | lymphocyte proliferation,NCI-H1975/GR cell lines | 50.94 % | 10.1007/s10600-014-1189-0 Chemistry of Natural Compounds |