SCS-C006221
DC1149B
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids
Class: Thiodiketopiperazine alkaloids
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
Penicillium ludwigii
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium ludwigii
South China Sea
DOI:
10.3389/fmicb.2022.857041
· Frontiers in Microbiology
Drug-likeness (Lipinski Ro5)
Molecular Weight
517.0 Da
Threshold ≤ 500
ALogP
0.84
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
10
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C20H21ClN2O8S2
Molecular Weight:
516.9810 Da
SMILES:
COc1ccc([C@H]2SS[C@@]34C[C@]5(O)[C@H](Cl)C=C[C@@H](O)[C@@H]5ON3C(=O)[C@@H]2NC4=O)c(O)c1OC
InChIKey:
CGVGJKPWGRDNTB-SVZWZRKASA-N
InChI:
InChI=1S/C20H21ClN2O8S2/c1-29-10-5-3-8(13(25)14(10)30-2)15-12-17(26)23-20(33-32-15,18(27)22-12)7-19(28)11(21)6-4-9(24)16(19)31-23/h3-6,9,11-12,15-16,24-25,28H,7H2,1-2H3,(H,22,27)/t9-,11-,12-,15-,16+,19+,20-/m1/s1
Calculated Properties
ALogP:
0.842 lipophilicity
TPSA:
137.79 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
10
Rotatable Bonds:
3
Ring Count:
6
(1 aromatic)
Chiral Centers:
7
Fsp³:
0.5000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006221
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Peptide alkaloids
NPClassifier Class:
Thiodiketopiperazine 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 |
|---|---|---|---|---|
| Antibacterial | MIC | Erysipelothrix rhusiopathiae WH13013 | 50.0–100.0 μg/ml | 10.3389/fmicb.2022.857041 Frontiers in Microbiology |
| Antibacterial | MIC | Streptococcus suis SC19 | 50.0–100.0 μg/ml | 10.3389/fmicb.2022.857041 Frontiers in Microbiology |
| Antitumor | IC50 | 22Rv1 cells | 13.6 μM | 10.3389/fmicb.2022.857041 Frontiers in Microbiology |
| Antitumor | IC50 | PC-3 cells | 5.1 μM | 10.3389/fmicb.2022.857041 Frontiers in Microbiology |
| Antitumor | inhibition | PC-3 cell colony formation | — Structured numeric value is not available in this record; see the primary reference. | 10.3389/fmicb.2022.857041 Frontiers in Microbiology |
| Cellular modulation | induction | PC-3 cell apoptosis | — Structured numeric value is not available in this record; see the primary reference. | 10.3389/fmicb.2022.857041 Frontiers in Microbiology |