SCS-C008394

Sch54794

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

Chemical Structure

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Source Information

Penicillium sp. (soft coral-derived fungus)

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

South China Sea

DOI: 10.13863/j.issn1001-4454.2008.07.008

Drug-likeness (Lipinski Ro5)

Molecular Weight

380.5 Da

Threshold ≤ 500

ALogP

2.57

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C18H24N2O3S2

Molecular Weight:

380.5350 Da

SMILES:

CS[C@@H]1NC(=O)[C@](Cc2ccc(OCC=C(C)C)cc2)(SC)NC1=O

InChIKey:

                        OUPACRHVFRGERT-WMZOPIPTSA-N
                        
                    

InChI:

InChI=1S/C18H24N2O3S2/c1-12(2)9-10-23-14-7-5-13(6-8-14)11-18(25-4)17(22)19-16(24-3)15(21)20-18/h5-9,16H,10-11H2,1-4H3,(H,19,22)(H,20,21)/t16-,18-/m0/s1

Calculated Properties

ALogP:

2.568 lipophilicity

TPSA:

67.43 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (1 aromatic)

Chiral Centers:

Fsp³:

0.4444 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008394

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
Antitumor	IC50	laryngeal carcinoma	33.0 μg/ml	10.13863/j.issn1001-4454.2008.07.008
Antitumor	IC50	hepatocellular carcinoma	25.0 μg/ml	10.13863/j.issn1001-4454.2008.07.008

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