SCS-C006093
citriperazine B
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
Lecanicillium kalimantanense
(NA)
Original source name: Lecanicillium kalimantanense | L. kalimantanense SCSIO41702
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Hypocreales
Family
Cordycipitaceae
Genus
Gamszarea
Species
Gamszarea kalimantanensis
South China Sea
DOI:
10.3390/md21110575
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
296.4 Da
Threshold ≤ 500
ALogP
1.22
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C13H16N2O2S2
Molecular Weight:
296.4170 Da
SMILES:
CS[C@@H]1NC(=O)[C@@](Cc2ccccc2)(SC)NC1=O
InChIKey:
LDOGKHFLRYUENB-WCQYABFASA-N
InChI:
InChI=1S/C13H16N2O2S2/c1-18-11-10(16)15-13(19-2,12(17)14-11)8-9-6-4-3-5-7-9/h3-7,11H,8H2,1-2H3,(H,14,17)(H,15,16)/t11-,13+/m0/s1
Calculated Properties
ALogP:
1.224 lipophilicity
TPSA:
58.20 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
4
Rotatable Bonds:
4
Ring Count:
2
(1 aromatic)
Chiral Centers:
2
Fsp³:
0.3846 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006093
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 |
|---|---|---|---|---|
| Antitumor Chemical note: cytotoxicity of thiodiketopiperazine alkaloids | structure-activity relationship | — | A comparison of the structures and cytotoxicities of 6, 7, and 19 suggested that lacking thiomethyl and benzene could significantly decrease the cytotoxicity of this type of alkaloids | 10.3390/md21110575 Marine Drugs |