SCS-C007181
bisdethiobis(methylthio)-acetylaranotin
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
Aspergillus sydowii
(coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus sydowii
South China Sea
DOI:
10.1016/j.fitote.2019.03.031
· Fitoterapia
Drug-likeness (Lipinski Ro5)
Molecular Weight
534.6 Da
Threshold ≤ 500
ALogP
2.04
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
10
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C24H26N2O8S2
Molecular Weight:
534.6120 Da
SMILES:
CS[C@@]12CC3=COC=C[C@H](OC(C)=O)[C@H]3N1C(=O)[C@]1(SC)CC3=COC=C[C@H](OC(C)=O)[C@H]3N1C2=O
InChIKey:
MNIWVYZRLOFLBX-KHTMQFLISA-N
InChI:
InChI=1S/C24H26N2O8S2/c1-13(27)33-17-5-7-31-11-15-9-23(35-3)22(30)26-20-16(12-32-8-6-18(20)34-14(2)28)10-24(26,36-4)21(29)25(23)19(15)17/h5-8,11-12,17-20H,9-10H2,1-4H3/t17-,18-,19-,20-,23+,24+/m0/s1
Calculated Properties
ALogP:
2.039 lipophilicity
TPSA:
111.68 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
10
Rotatable Bonds:
4
Ring Count:
5
(0 aromatic)
Chiral Centers:
6
Fsp³:
0.5000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007181
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 | — | Methicillin-resistant Staphyloccocus aureus; Staphyloccocus aureus; Enterococcus faecalis; Escherichia coli; Klebsiella pneumoniae | none of compounds showed antibacterial and cytotoxic activities | 10.1016/j.fitote.2019.03.031 Fitoterapia |
| Antitumor | — | K562; SGC-7901; A549; Hela cell lines | none of compounds showed antibacterial and cytotoxic activities | 10.1016/j.fitote.2019.03.031 Fitoterapia |
| Antitumor | — | MDCK cells | > 200.0 μM | 10.1016/j.fitote.2019.03.031 Fitoterapia |