SCS-C000040
rabelomycin
Pathway: Polyketides
Superclass: Polycyclic aromatic polyketides
Class: Angucyclines
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
Micromonospora rosaria
(NA)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Micromonosporales
Family
Micromonosporaceae
Genus
Micromonospora
Species
Micromonospora rosaria
South China Sea
· -30m
· E 116°17.754', N 22°41.083'
DOI:
10.1021/np300505y
· Journal of Natural Products
Streptomyces globisporus SCSIO LCY30
(NA)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces globisporus
South China Sea
DOI:
10.3390/md22010021
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
338.3 Da
Threshold ≤ 500
ALogP
1.75
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C19H14O6
Molecular Weight:
338.3000 Da
SMILES:
C[C@]1(O)CC(=O)c2c(cc(O)c3c2C(=O)c2cccc(O)c2C3=O)C1
InChIKey:
JJOLHRYZQSDLSA-LJQANCHMSA-N
InChI:
InChI=1S/C19H14O6/c1-19(25)6-8-5-11(21)15-16(13(8)12(22)7-19)17(23)9-3-2-4-10(20)14(9)18(15)24/h2-5,20-21,25H,6-7H2,1H3/t19-/m1/s1
Calculated Properties
ALogP:
1.753 lipophilicity
TPSA:
111.90 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
6
Rotatable Bonds:
0
Ring Count:
4
(2 aromatic)
Chiral Centers:
1
Fsp³:
0.2105 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000040
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Polycyclic aromatic polyketides
NPClassifier Class:
Angucyclines
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 | Escherichia coli ATCC 25922 | 16.0 μg/mL | 10.1021/np300505y Journal of Natural Products |
| Antibacterial | MIC | Staphylococcus aureus ATCC 29213 | 1.0 μg/mL | 10.1021/np300505y Journal of Natural Products |
| Antibacterial | MIC | Bacillus thuringiensis SCSIO BT01 | 8.0 μg/mL | 10.1021/np300505y Journal of Natural Products |
| Antibacterial | MIC | Bacillus subtilis SCSIO BS01 | 16.0 μg/mL | 10.1021/np300505y Journal of Natural Products |
| Antitumor | IC50 | SF-268 | 5.54 ± 0.05 μM | 10.1021/np300505y Journal of Natural Products |
| Antitumor | IC50 | MCF-7 | 4.28 ± 0.08 μM | 10.1021/np300505y Journal of Natural Products |
| Antitumor | IC50 | NCI-H460 | 9.91 ± 0.08 μM | 10.1021/np300505y Journal of Natural Products |
| Antibacterial | MIC | Micrococcus luteus ML01 | 2.0 μg/mL | 10.3390/md22010021 Marine Drugs |
| Antitumor | IC50 | SW480 cells | 1.57 μM | 10.3390/md22010021 Marine Drugs |