SCS-C007519
borrelidin A
Pathway: Polyketides
Superclass: Macrolides
Class: Erythromycins
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 olivaceus SCSIO LO13
(NA)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces olivaceus
South China Sea
· N22°33′13.71″, E114°31′09.20″
DOI:
10.1002/cbdv.201900560
· Chemistry & Biodiversity
Drug-likeness (Lipinski Ro5)
Molecular Weight
489.7 Da
Threshold ≤ 500
ALogP
4.64
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:
C28H43NO6
Molecular Weight:
489.6530 Da
SMILES:
C[C@@H]1C[C@H](C)C[C@H](C)[C@@H](O)CC(=O)O[C@H]([C@@H]2CCC[C@H]2C(=O)O)C/C=C/C=C(/C#N)[C@H](O)[C@@H](C)C1
InChIKey:
OJCKRNPLOZHAOU-UGKRXNSESA-N
InChI:
InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1
Calculated Properties
ALogP:
4.636 lipophilicity
TPSA:
127.85 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
6
Rotatable Bonds:
2
Ring Count:
2
(0 aromatic)
Chiral Centers:
9
Fsp³:
0.7500 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007519
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Macrolides
NPClassifier Class:
Erythromycins
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 | IC50 | A549; HeLa; HepG2; MCF7; RKO | Compound 4 showed strong cytotoxic activities against all cell lines. | 10.1002/cbdv.201900560 Chemistry & Biodiversity |
| Antibacterial | MIC | Micrococcus luteus | < 0.5 μM | 10.1002/cbdv.201900560 Chemistry & Biodiversity |