SCS-C006222

outovirin B

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

Chemical Structure

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Source Information

Penicillium ludwigii (NA)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species Penicillium ludwigii

South China Sea

DOI: 10.3389/fmicb.2022.857041 · Frontiers in Microbiology

Drug-likeness (Lipinski Ro5)

Molecular Weight

497.5 Da

Threshold ≤ 500

ALogP

-1.00

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (HBA) — borderline drug-like

Chemical Properties

Molecular Formula:

C20H21N2O9S2-

Molecular Weight:

497.5270 Da

SMILES:

COc1c([O-])ccc(C2SS[C@]34C[C@@]5(O)[C@H](O)C=CC(O)[C@@H]5ON3C(=O)[C@@H]2N(C)C4=O)c1O

InChIKey:

                        GGFPUTLKQMUZQF-OQURITATSA-M
                        
                    

InChI:

InChI=1S/C20H22N2O9S2/c1-21-12-15(8-3-4-9(23)14(30-2)13(8)26)32-33-20(18(21)28)7-19(29)11(25)6-5-10(24)16(19)31-22(20)17(12)27/h3-6,10-12,15-16,23-26,29H,7H2,1-2H3/p-1/t10?,11-,12-,15?,16+,19-,20+/m1/s1

Calculated Properties

ALogP:

-0.997 lipophilicity

TPSA:

163.06 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (1 aromatic)

Chiral Centers:

Fsp³:

0.5000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006222

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	Erysipelothrix rhusiopathiae WH13013	50.0–100.0 μg/ml	10.3389/fmicb.2022.857041 Frontiers in Microbiology
Antibacterial	MIC	Streptococcus suis SC19	50.0–100.0 μg/ml	10.3389/fmicb.2022.857041 Frontiers in Microbiology

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