SCS-C006828
tirandamycin C
Pathway: Polyketides
Superclass: Linear polyketides
Class: 3-oligoenoyltetramic acids
Chemical Structure
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Streptomyces sp. SCSIO 1666
(bacterium)
Original source name: Streptomyces sp. SCSIO1666
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces sp. SCSIO1666
South China Sea
DOI:
10.1016/j.bbrc.2011.02.040
· Biochemical and Biophysical Research Communications
Drug-likeness (Lipinski Ro5)
Molecular Weight
387.5 Da
Threshold ≤ 500
ALogP
3.12
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H29NO5
Molecular Weight:
387.4760 Da
SMILES:
CC1=CC[C@H]2O[C@]1(C)O[C@H]([C@H](C)/C=C(C)/C=C/C(O)=C1/C(=O)CNC1=O)[C@H]2C
InChIKey:
WWRZQUIPJGHZFD-IVGQTCGHSA-N
InChI:
InChI=1S/C22H29NO5/c1-12(6-8-16(24)19-17(25)11-23-21(19)26)10-13(2)20-15(4)18-9-7-14(3)22(5,27-18)28-20/h6-8,10,13,15,18,20,24H,9,11H2,1-5H3,(H,23,26)/b8-6+,12-10+,19-16+/t13-,15+,18-,20-,22-/m1/s1
Calculated Properties
ALogP:
3.122 lipophilicity
TPSA:
84.86 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
5
Rotatable Bonds:
4
Ring Count:
3
(0 aromatic)
Chiral Centers:
5
Fsp³:
0.5455 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006828
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Linear polyketides
NPClassifier Class:
3-oligoenoyltetramic acids
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 | — | bacterial RNA polymerase | The tirandamycins (1–4, Fig. 1) belong to a small group of naturally occurring tetramic acid antibiotics that exhibited broad biological activities, such as antiviral, antiulcerative, antitumor, and antibacterial properties | 10.1016/j.bbrc.2011.02.040 Biochemical and Biophysical Research Communications |