SCS-C006301

tirandamycin B

Pathway: Polyketides Superclass: Linear polyketides Class: 3-oligoenoyltetramic acids

Chemical Structure

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Download: SDF SMILES

Source Information

Streptomyces tirandamycinicus (NA)

Original source name: Streptomyces tirandamycinicus sp. nov.

Kingdom Bacillati Phylum Actinomycetota Class Actinomycetes Order Kitasatosporales Family Streptomycetaceae Genus Streptomyces Species Streptomyces tirandamycinicus

South China Sea

DOI: 10.3389/fmicb.2019.00482 · Frontiers in Microbiology

Drug-likeness (Lipinski Ro5)

Molecular Weight

447.5 Da

Threshold ≤ 500

ALogP

0.88

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C23H29NO8

Molecular Weight:

447.4840 Da

SMILES:

CC(/C=C/C(O)=C1/C(=O)CNC1=O)=C\[C@@H](C)[C@H]1OC2(C)O[C@@H](C(=O)[C@@H]3O[C@@]32CO)C1(C)C

InChIKey:

                        JCLWWXZEPQGIAJ-SCMMSBPUSA-N
                        
                    

InChI:

InChI=1S/C23H29NO8/c1-11(6-7-13(26)15-14(27)9-24-20(15)29)8-12(2)17-21(3,4)18-16(28)19-23(10-25,32-19)22(5,30-17)31-18/h6-8,12,17-19,25-26H,9-10H2,1-5H3,(H,24,29)/b7-6+,11-8+,15-13+/t12-,17-,18+,19+,22?,23+/m1/s1

Calculated Properties

ALogP:

0.875 lipophilicity

TPSA:

134.69 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.6087 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006301

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Linear polyketides

NPClassifier Class:

3-oligoenoyltetramic acids

Glycoside:

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	Streptococcus agalactiae HNe0	2.55 μg/mL	10.3389/fmicb.2019.00482 Frontiers in Microbiology
Antibacterial	MIC	Bacillus subtilis GIM1.222	6.8 μg/mL	10.3389/fmicb.2019.00482 Frontiers in Microbiology
Antibacterial	MIC	Staphylococcus aureus GIM1.221, Escherichia coli GIM1.223	> 128.0 μg/mL	10.3389/fmicb.2019.00482 Frontiers in Microbiology

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