SCS-C005959
bafilomycin B1
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 cavourensis
(NA)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces cavourensis
South China Sea
· 1464 m
DOI:
10.4014/jmb.1407.07025
· Journal of Microbiology and Biotechnology
Drug-likeness (Lipinski Ro5)
Molecular Weight
814.0 Da
Threshold ≤ 500
ALogP
5.55
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
12
Threshold ≤ 10
3 violations (MW, ALogP, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C45H67NO12
Molecular Weight:
814.0260 Da
SMILES:
CO/C1=C\C(C)=C\[C@H](C)[C@H](O)[C@@H](C)C/C(C)=C/C=C/[C@@H](OC)[C@H]([C@H](C)[C@H](O)[C@@H](C)[C@]2(O)C[C@H](OC(=O)/C=C/C(=O)NC3=C(C)CCC3=O)[C@@H](C)[C@H](C(C)C)O2)OC1=O
InChIKey:
FIKHYVBISKHDAF-AEUJPWFRSA-N
InChI:
InChI=1S/C45H67NO12/c1-24(2)42-30(8)36(56-38(49)19-18-37(48)46-39-27(5)16-17-33(39)47)23-45(53,58-42)32(10)41(51)31(9)43-34(54-11)15-13-14-25(3)20-28(6)40(50)29(7)21-26(4)22-35(55-12)44(52)57-43/h13-15,18-19,21-22,24,28-32,34,36,40-43,50-51,53H,16-17,20,23H2,1-12H3,(H,46,48)/b15-13+,19-18+,25-14+,26-21+,35-22-/t28-,29-,30+,31+,32+,34+,36-,40+,41-,42-,43-,45-/m0/s1
Calculated Properties
ALogP:
5.553 lipophilicity
TPSA:
187.15 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
12
Rotatable Bonds:
11
Ring Count:
3
(0 aromatic)
Chiral Centers:
12
Fsp³:
0.6444 fraction sp³ carbon
Database Information
Compound ID:
SCS-C005959
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 |
|---|---|---|---|---|
| Antifungal | inhibition zone diameter | Fusarium oxysporum f. sp. corylus chinensis | 19.93 mm | 10.4014/jmb.1407.07025 Journal of Microbiology and Biotechnology |
| Antifungal | inhibition zone diameter | multiple Fusarium spp.; Botrytis cinerea | compound 2 showed a stronger activity and a wider antifungal spectrum than compound 1 | 10.4014/jmb.1407.07025 Journal of Microbiology and Biotechnology |