SCS-C007868
9,9′-diene-11,13,11′,13′-tetra-O-methylelaiolide
Pathway: Polyketides
Superclass: Macrolides
Class: Bafilomycins
Glycoside
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 malaysiensis
(NA)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces malaysiensis
South China Sea
DOI:
10.1021/acs.jnatprod.1c00297
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
785.1 Da
Threshold ≤ 500
ALogP
8.87
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
10
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C46H72O10
Molecular Weight:
785.0720 Da
SMILES:
CC[C@@H]1[C@@H](C)O[C@@](OC)(/C(C)=C/[C@H](C)[C@H]2OC(=O)/C=C/C=C/[C@H](C)[C@@H]([C@@H](C)/C=C(\C)[C@@]3(OC)C[C@@H](OC)[C@H](CC)[C@@H](C)O3)OC(=O)/C=C/C=C/[C@@H]2C)C[C@H]1OC
InChIKey:
NRTYBSNXQFTVTP-BPMREDQYSA-N
InChI:
InChI=1S/C46H72O10/c1-15-37-35(9)55-45(51-13,27-39(37)49-11)33(7)25-31(5)43-29(3)21-17-19-24-42(48)54-44(30(4)22-18-20-23-41(47)53-43)32(6)26-34(8)46(52-14)28-40(50-12)38(16-2)36(10)56-46/h17-26,29-32,35-40,43-44H,15-16,27-28H2,1-14H3/b21-17+,22-18+,23-20+,24-19+,33-25+,34-26+/t29-,30-,31-,32-,35+,36+,37+,38+,39+,40+,43-,44-,45+,46+/m0/s1
Calculated Properties
ALogP:
8.871 lipophilicity
TPSA:
107.98 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
10
Rotatable Bonds:
12
Ring Count:
3
(0 aromatic)
Chiral Centers:
14
Fsp³:
0.6957 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007868
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Macrolides
NPClassifier Class:
Bafilomycins
Glycoside:
Yes
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 | tested cancer cell lines | compounds 1, 4, 5, and 7 showed cytotoxicity against some or all of the five cancer cell lines with IC50 values ranging from 0.067 to 7.2 μM. | 10.1021/acs.jnatprod.1c00297 Journal of Natural Products |