SCS-C001358

Piericidin glycoside

Pathway: Polyketides Glycoside

Chemical Structure

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Download: SDF SMILES

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

593.7 Da

Threshold ≤ 500

ALogP

2.25

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

3 violations (MW, HBD, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C31H47NO10

Molecular Weight:

593.7140 Da

SMILES:

COc1nc(C/C=C(\C)C/C=C/C(C)=C/[C@@H](C)[C@@H](O[C@@H]2OC(CO)[C@@H](O)[C@H](O)C2O)/C(C)=C/CO)c(C)c(O)c1OC

InChIKey:

                        ZNDBGWYPOYJCKZ-ACIYCDNASA-N
                        
                    

InChI:

InChI=1S/C31H47NO10/c1-17(11-12-22-21(5)24(35)29(39-6)30(32-22)40-7)9-8-10-18(2)15-20(4)28(19(3)13-14-33)42-31-27(38)26(37)25(36)23(16-34)41-31/h8,10-11,13,15,20,23,25-28,31,33-34,36-38H,9,12,14,16H2,1-7H3,(H,32,35)/b10-8+,17-11+,18-15+,19-13+/t20-,23?,25-,26+,27?,28+,31+/m1/s1

Calculated Properties

ALogP:

2.254 lipophilicity

TPSA:

171.19 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (1 aromatic)

Chiral Centers:

Fsp³:

0.5806 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001358

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

N/A

NPClassifier Class:

N/A

Glycoside:

Yes

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)	7.21 μM	10.1021/acs.jmedchem.9b00598 Journal of Medicinal Chemistry

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