SCS-C000608

tirandamycin C2

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

Chemical Structure

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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: 10.1021/ol200447h · Organic Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight

403.5 Da

Threshold ≤ 500

ALogP

2.09

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H29NO6

Molecular Weight:

403.5000 Da

SMILES:

CC1=C[C@@H](O)C2OC1(C)O[C@H]([C@H](C)/C=C(C)/C=C/C(O)=C1\C(=O)CNC1=O)[C@H]2C

InChIKey:

                        ADEAEUKXVJOXIM-AOYOPVBSSA-N
                        
                    

InChI:

InChI=1S/C22H29NO6/c1-11(6-7-15(24)18-17(26)10-23-21(18)27)8-12(2)19-14(4)20-16(25)9-13(3)22(5,28-19)29-20/h6-9,12,14,16,19-20,24-25H,10H2,1-5H3,(H,23,27)/b7-6+,11-8+,18-15-/t12-,14-,16-,19-,20?,22?/m1/s1

Calculated Properties

ALogP:

2.093 lipophilicity

TPSA:

105.09 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (0 aromatic)

Chiral Centers:

Fsp³:

0.5455 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000608

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	—	Gram-positive bacteria	antibacterial	10.1021/ol200447h Organic Letters

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