SCS-C001194

emestrin M

Pathway: Alkaloids | Amino acids and Peptides Superclass: Peptide alkaloids Class: Thiodiketopiperazine alkaloids

Chemical Structure

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Source Information

Aspergillus terreus RA2905 (mangrove endophytic fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus terreus

Beibu Gulf

DOI: 10.3390/md18030132 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

434.5 Da

Threshold ≤ 500

ALogP

1.57

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C20H22N2O5S2

Molecular Weight:

434.5000 Da

SMILES:

CS[C@@]1(Cc2ccccc2O)NC(=O)[C@]2(SC)CC3=COC=C[C@H](O)[C@H]3N2C1=O

InChIKey:

                        BXICUEGSLMRXKC-XAMWDVODSA-N
                        
                    

InChI:

InChI=1S/C20H22N2O5S2/c1-28-19(9-12-5-3-4-6-14(12)23)18(26)22-16-13(11-27-8-7-15(16)24)10-20(22,29-2)17(25)21-19/h3-8,11,15-16,23-24H,9-10H2,1-2H3,(H,21,25)/t15-,16-,19+,20+/m0/s1

Calculated Properties

ALogP:

1.573 lipophilicity

TPSA:

99.10 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (1 aromatic)

Chiral Centers:

Fsp³:

0.4000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001194

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

Thiodiketopiperazine alkaloids

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	Pseudomonas aeruginosa ATCC 27853	64.0 μg/mL	10.3390/md18030132 Marine Drugs

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