SCS-C007033
somamycin A
Pathway: Amino acids and Peptides | Polyketides
Superclass: Macrolides
Class: Macrocyclic tetramic 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 somaliensis
(NA)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces somaliensis
South China Sea
· 3536 m
DOI:
10.1016/j.bioorg.2020.103954
· Bioorganic Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
510.6 Da
Threshold ≤ 500
ALogP
1.96
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C29H38N2O6
Molecular Weight:
510.6310 Da
SMILES:
C=C[C@@H]1C[C@@H]2C[C@@H]3[C@H]4C/C=C\C(=O)NCC[C@H](O)[C@H]5NC(=O)C(=C5O)C(=O)/C=C/[C@@H]4C[C@H](O)[C@H]3[C@@H]2[C@H]1C
InChIKey:
LGWIKXPOEGBEOB-JIHNEDJNSA-N
InChI:
InChI=1S/C29H38N2O6/c1-3-15-11-17-12-19-18-5-4-6-23(35)30-10-9-21(33)27-28(36)26(29(37)31-27)20(32)8-7-16(18)13-22(34)25(19)24(17)14(15)2/h3-4,6-8,14-19,21-22,24-25,27,33-34,36H,1,5,9-13H2,2H3,(H,30,35)(H,31,37)/b6-4-,8-7+/t14-,15+,16+,17+,18-,19+,21-,22-,24+,25-,27+/m0/s1
Calculated Properties
ALogP:
1.957 lipophilicity
TPSA:
135.96 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
6
Rotatable Bonds:
1
Ring Count:
5
(0 aromatic)
Chiral Centers:
11
Fsp³:
0.6207 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007033
NPClassifier Pathway:
Amino acids and Peptides
Polyketides
NPClassifier Superclass:
Macrolides
NPClassifier Class:
Macrocyclic tetramic 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 |
|---|---|---|---|---|
| Antifungal | MIC | Fusarium oxysporum MHKW | 1.6 μg/mL | 10.1016/j.bioorg.2020.103954 Bioorganic Chemistry |
| Antifungal | MIC | Alternaria brassicae BCHB | 3.1 μg/mL | 10.1016/j.bioorg.2020.103954 Bioorganic Chemistry |
| Antitumor | IC50 | HCT116 human cancer cell line | 0.6 μM | 10.1016/j.bioorg.2020.103954 Bioorganic Chemistry |
| Antitumor | IC50 | K562 human cancer cell line | 1.5 μM | 10.1016/j.bioorg.2020.103954 Bioorganic Chemistry |