SCS-C006228
USF-19A
Pathway: Amino acids and Peptides | Polyketides
Superclass: Macrolides
Class: Antimycins
Chemical Structure
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Streptomyces somaliensis SCSIO ZH66
(NA)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces somaliensis
South China Sea
· 3536 m
· 120° 0.250'E; 20° 22.971'N
DOI:
10.3389/fmicb.2017.00678
· Frontiers in Microbiology
Drug-likeness (Lipinski Ro5)
Molecular Weight
464.5 Da
Threshold ≤ 500
ALogP
1.14
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H28N2O9
Molecular Weight:
464.4710 Da
SMILES:
CC(C)C(=O)O[C@H]1[C@H](C)OC(=O)[C@@H](NC(=O)c2cccc(NC=O)c2O)[C@@H](C)OC(=O)[C@@H]1C
InChIKey:
WJILAMJSXMNDKI-YEWWMAIHSA-N
InChI:
InChI=1S/C22H28N2O9/c1-10(2)20(28)33-18-11(3)21(29)31-12(4)16(22(30)32-13(18)5)24-19(27)14-7-6-8-15(17(14)26)23-9-25/h6-13,16,18,26H,1-5H3,(H,23,25)(H,24,27)/t11-,12-,13+,16+,18-/m1/s1
Calculated Properties
ALogP:
1.140 lipophilicity
TPSA:
157.33 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
9
Rotatable Bonds:
6
Ring Count:
2
(1 aromatic)
Chiral Centers:
5
Fsp³:
0.5000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006228
NPClassifier Pathway:
Amino acids and Peptides
Polyketides
NPClassifier Superclass:
Macrolides
NPClassifier Class:
Antimycins
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 |
|---|---|---|---|---|
| Anti-inflammatory | IC50 | IL-5 cytokine | 0.57 μM | 10.3389/fmicb.2017.00678 Frontiers in Microbiology |
| Antitumor | LD50 | Human umbilical vein endothelial cells (HUVEC) | 34.6 μM | 10.3389/fmicb.2017.00678 Frontiers in Microbiology |
| Antibacterial | inhibition zone | Five multi-drug resistant bacterial strains: S. aureus CCARM 3090, E. coli CCARM 1009, E. faecalis CCARM 5172, E. faecium CCARM 5203, S. typhimurium CCARM 8250 | 0.0 mm | 10.3389/fmicb.2017.00678 Frontiers in Microbiology |