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SCS-C005941

O-β-kijanosyl-(1→17)-kijanolide

Pathway: Polyketides Superclass: Macrolides Class: Spirotetronate macrolides Glycoside
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Chemical Structure

Structure of O-β-kijanosyl-(1→17)-kijanolide
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Download: SDF SMILES

Source Information

Streptomyces sp. 12A35 (bacterium)
Kingdom Bacillati Phylum Actinomycetota Class Actinomycetes Order Kitasatosporales Family Streptomycetaceae Genus Streptomyces Species NA
South China Sea  · 2134 m  · 17°59.928'N, 111°36.160'E
DOI: 10.3390/md11103891  · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight
782.9 Da
Threshold ≤ 500
ALogP
4.99
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
13
Threshold ≤ 10
2 violations (MW, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C42H58N2O12
Molecular Weight:
782.9280 Da
SMILES:
CC(=O)ONC1C(C)OC(O[C@H]2C/C=C(\C)[C@@H]3C=C[C@@H]4[C@@H](O)[C@@H](C)C[C@H](C)[C@H]4[C@]3(C)C(=O)C3=C(O)[C@@]4(C[C@@H](C)C(CO)=C[C@H]4/C=C/2C)OC3=O)CC1(C)[N+](=O)[O-]
InChIKey:
VIQNENZSZJPBJM-YPVNDDKISA-N
InChI:
InChI=1S/C42H58N2O12/c1-20-10-13-31(54-32-18-40(8,44(51)52)36(25(6)53-32)43-56-26(7)46)21(2)15-28-16-27(19-45)24(5)17-42(28)38(49)33(39(50)55-42)37(48)41(9)30(20)12-11-29-34(41)22(3)14-23(4)35(29)47/h10-12,15-16,22-25,28-32,34-36,43,45,47,49H,13-14,17-19H2,1-9H3/b20-10+,21-15+/t22-,23-,24+,25?,28+,29-,30-,31-,32?,34+,35-,36?,40?,41+,42-/m0/s1
Calculated Properties
ALogP:
4.987 lipophilicity
TPSA:
203.99 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
13
Rotatable Bonds:
6
Ring Count:
6 (0 aromatic)
Chiral Centers:
15
Fsp³:
0.6905 fraction sp³ carbon

Database Information

Compound ID:
SCS-C005941
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Macrolides
NPClassifier Class:
Spirotetronate macrolides
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

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 Bacillus subtilis 50.0 μg/mL 10.3390/md11103891 Marine Drugs
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Structure enlarged