SCS-C001357

Glucopiericidin A

Pathway: Polyketides Glycoside

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

577.7 Da

Threshold ≤ 500

ALogP

2.87

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C31H47NO9

Molecular Weight:

577.7000 Da

SMILES:

C/C=C(\C)[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](C)/C=C(C)/C=C/C/C(C)=C/Cc1[nH]c(OC)c(OC)c(=O)c1C

InChIKey:

                        YQOARHMNLCWEPG-DFTUVXBYSA-N
                        
                    

InChI:

InChI=1S/C31H47NO9/c1-9-19(4)28(41-31-27(37)26(36)25(35)23(16-33)40-31)20(5)15-18(3)12-10-11-17(2)13-14-22-21(6)24(34)29(38-7)30(32-22)39-8/h9-10,12-13,15,20,23,25-28,31,33,35-37H,11,14,16H2,1-8H3,(H,32,34)/b12-10+,17-13+,18-15+,19-9+/t20-,23-,25-,26+,27-,28+,31+/m1/s1

Calculated Properties

ALogP:

2.869 lipophilicity

TPSA:

150.70 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-C001357

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

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