SCS-C006300
tirandamycin A
Pathway: Polyketides
Superclass: Linear polyketides
Class: 3-oligoenoyltetramic acids
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
Streptomyces tirandamycinicus
(NA)
Original source name: Streptomyces tirandamycinicus sp. nov.
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces tirandamycinicus
South China Sea
DOI:
10.3389/fmicb.2019.00482
· Frontiers in Microbiology
Drug-likeness (Lipinski Ro5)
Molecular Weight
445.5 Da
Threshold ≤ 500
ALogP
2.15
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C24H31NO7
Molecular Weight:
445.5120 Da
SMILES:
CC(/C=C/C(O)=C1/C(=O)CNC1=O)=C\[C@@H](C)[C@H]1OC2(C)O[C@@H](C(=O)[C@@H]3O[C@@]32C)C(C)C1C
InChIKey:
ZTPDFGAEFXTNFK-RNIVADNFSA-N
InChI:
InChI=1S/C24H31NO7/c1-11(7-8-15(26)17-16(27)10-25-22(17)29)9-12(2)19-13(3)14(4)20-18(28)21-23(5,32-21)24(6,30-19)31-20/h7-9,12-14,19-21,26H,10H2,1-6H3,(H,25,29)/b8-7+,11-9+,17-15+/t12-,13?,14?,19-,20-,21+,23+,24?/m1/s1
Calculated Properties
ALogP:
2.149 lipophilicity
TPSA:
114.46 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
7
Rotatable Bonds:
4
Ring Count:
4
(0 aromatic)
Chiral Centers:
8
Fsp³:
0.6250 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006300
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Linear polyketides
NPClassifier Class:
3-oligoenoyltetramic acids
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 | Streptococcus agalactiae HNe0 | 2.52 μg/mL | 10.3389/fmicb.2019.00482 Frontiers in Microbiology |
| Antibacterial | MIC | Bacillus subtilis GIM1.222 | 5.5 μg/mL | 10.3389/fmicb.2019.00482 Frontiers in Microbiology |
| Antibacterial | MIC | Staphylococcus aureus GIM1.221, Escherichia coli GIM1.223 | > 128.0 μg/mL | 10.3389/fmicb.2019.00482 Frontiers in Microbiology |