SCS-C007346

Leuchagodine B

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

330.3 Da

Threshold ≤ 500

ALogP

0.81

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C15H18N6O3

Molecular Weight:

330.3480 Da

SMILES:

CN/C(N)=N\C(=O)Nc1nc(Cc2ccc3c(c2)OCO3)cn1C

InChIKey:

                        UWCAAKSJPAYJFU-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C15H18N6O3/c1-17-13(16)19-15(22)20-14-18-10(7-21(14)2)5-9-3-4-11-12(6-9)24-8-23-11/h3-4,6-7H,5,8H2,1-2H3,(H4,16,17,18,19,20,22)

Calculated Properties

ALogP:

0.806 lipophilicity

TPSA:

115.79 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.2667 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007346

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
Anti-inflammatory	inhibitory activity	LPS-induced TNF-α production	— Structured numeric value is not available in this record; see the primary reference.	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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