SCS-C000605

isotirandamycin B

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.

Download: SDF SMILES

Source Information

Streptomyces sp. SCSIO 41399 (bacterium)

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

South China Sea

DOI: 10.1038/s41429-018-0103-6 · The Journal of Antibiotics

Drug-likeness (Lipinski Ro5)

Molecular Weight

433.5 Da

Threshold ≤ 500

ALogP

0.48

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H27NO8

Molecular Weight:

433.5000 Da

SMILES:

CC(C=CC(O)=C1C(=O)CNC1=O)=C[C@@H](C)[C@H]1O[C@@]2(C)O[C@H](C(=O)[C@@H]3O[C@@]32CO)[C@@H]1C

InChIKey:

                        LYJKREGDQDJIDC-RXSAWIGCSA-N
                        
                    

InChI:

InChI=1S/C22H27NO8/c1-10(5-6-13(25)15-14(26)8-23-20(15)28)7-11(2)17-12(3)18-16(27)19-22(9-24,31-19)21(4,29-17)30-18/h5-7,11-12,17-19,24-25H,8-9H2,1-4H3,(H,23,28)/t11-,12-,17-,18+,19+,21+,22+/m1/s1

Calculated Properties

ALogP:

0.485 lipophilicity

TPSA:

134.69 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.5909 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000605

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	5.7–11.5 μM	10.1038/s41429-018-0103-6 The Journal of Antibiotics

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