SCS-C007349

Bis(pyronaamidine)zinc

Pathway: Alkaloids Superclass: Histidine alkaloids Class: Imidazole alkaloids

Chemical Structure

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Download: SDF SMILES

Source Information

Leucetta chagosensis (calcareous marine sponge)

Kingdom Metazoa Phylum Porifera Class Calcarea Order Clathrinida Family Leucettidae Genus Leucetta Species Leucetta chagosensis

South China Sea

DOI: 10.1021/acs.jnatprod.7b01006 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

1050.4 Da

Threshold ≤ 500

ALogP

6.66

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

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

Chemical Properties

Molecular Formula:

C50H52N10O12Zn

Molecular Weight:

1050.4140 Da

SMILES:

COc1ccc(Cc2nc([N-]C3=NC(=O)N(C)C3=O)n(C)c2Cc2ccc(OC)c(OC)c2O)cc1.COc1ccc(Cc2nc([N-]C3=NC(=O)N(C)C3=O)n(C)c2Cc2ccc(OC)c(OC)c2O)cc1.[Zn+2]

InChIKey:

                        YYONOPNKAQCKOT-UHFFFAOYSA-L
                        
                    

InChI:

InChI=1S/2C25H27N5O6.Zn/c2*1-29-18(13-15-8-11-19(35-4)21(36-5)20(15)31)17(12-14-6-9-16(34-3)10-7-14)26-24(29)27-22-23(32)30(2)25(33)28-22;/h2*6-11H,12-13H2,1-5H3,(H2,26,27,28,31,33);/q;;+2/p-2

Calculated Properties

ALogP:

6.655 lipophilicity

TPSA:

259.16 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (6 aromatic)

Chiral Centers:

Fsp³:

0.2800 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007349

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Histidine alkaloids

NPClassifier Class:

Imidazole 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
Anti-inflammatory	inhibitory activity	LPS-induced IL-6 production	THP-1 cells pretreated with 2 and 5 at 10 μM showed decreases in the LPS-induced production of IL-6 (P<0.05 for 2 and P<0.01 for 5).	10.1021/acs.jnatprod.7b01006 Journal of Natural Products
Antitumor	IC50	A549, PC9, MCF-7 human cancer cell lines	> 20.0 μM	10.1021/acs.jnatprod.7b01006 Journal of Natural Products

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