SCS-C001355

Piericidin derivative

Pathway: Polyketides

Chemical Structure

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Source Information

Streptomyces psammoticus (Streptomyces)

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

Pearl River Estuary · -5m · E 113°33′11.15″, N22°53′40.16″

DOI: 10.1021/acs.jmedchem.9b00598 · Journal of Medicinal Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

445.6 Da

Threshold ≤ 500

ALogP

5.06

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:

C26H39NO5

Molecular Weight:

445.6000 Da

SMILES:

COc1nc(C/C=C(\C)C/C(C)=C/C(C)=C/[C@@H](C)[C@@H](O)[C@]2(C)O[C@H]2C)c(C)c(O)c1OC

InChIKey:

                        XOTNBTWLMWQADF-UUOARQPGSA-N
                        
                    

InChI:

InChI=1S/C26H39NO5/c1-15(10-11-21-19(5)22(28)23(30-8)25(27-21)31-9)12-16(2)13-17(3)14-18(4)24(29)26(7)20(6)32-26/h10,13-14,18,20,24,29H,11-12H2,1-9H3,(H,27,28)/b15-10+,16-13+,17-14+/t18-,20+,24-,26-/m1/s1

Calculated Properties

ALogP:

5.059 lipophilicity

TPSA:

84.34 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (1 aromatic)

Chiral Centers:

Fsp³:

0.5769 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001355

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

N/A

NPClassifier Class:

N/A

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	Peroxiredoxin 1 (PRDX1)	> 100.0 μM	10.1021/acs.jmedchem.9b00598 Journal of Medicinal Chemistry

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