SCS-C006603

chrysomycin B

Pathway: Polyketides Superclass: Polycyclic aromatic polyketides Class: Angucyclines

Chemical Structure

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Source Information

Streptomyces sp. (bacterium)

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

South China Sea · ?3000 m

DOI: 10.3390/md22060259 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

496.5 Da

Threshold ≤ 500

ALogP

3.06

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H28O9

Molecular Weight:

496.5120 Da

SMILES:

COc1cc2c(oc(=O)c3cc(C)cc(OC)c32)c2c([C@H]3O[C@@H](C)[C@@H](O)[C@](C)(O)[C@@H]3O)ccc(O)c12

InChIKey:

                        BJPYMDSMDBCKEP-HURHZEBWSA-N
                        
                    

InChI:

InChI=1S/C27H28O9/c1-11-8-15-19(17(9-11)33-4)14-10-18(34-5)21-16(28)7-6-13(20(21)22(14)36-26(15)31)23-25(30)27(3,32)24(29)12(2)35-23/h6-10,12,23-25,28-30,32H,1-5H3/t12-,23+,24+,25+,27-/m0/s1

Calculated Properties

ALogP:

3.063 lipophilicity

TPSA:

138.82 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (4 aromatic)

Chiral Centers:

Fsp³:

0.3704 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006603

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Polycyclic aromatic polyketides

NPClassifier Class:

Angucyclines

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
Antimycobacterial	MIC	wild-type Mycobacterium tuberculosis and clinically isolated MDR M. tuberculosis strains	1.56–6.25 μg/mL	10.3390/md22060259 Marine Drugs
Antibacterial	MIC	Staphylococcus aureus (ATCC 6538), methicillin-resistant S. aureus (MRSA), Streptococcus pneumoniae (ATCC 49619)	3.12–25.0 μg/mL	10.3390/md22060259 Marine Drugs
Antifungal	inhibition	Candida albicans	no inhibition against C. albicans	10.3390/md22060259 Marine Drugs

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