SCS-C006453

6-(2-amino-4-oxo-1H,5H-imidazol-5-yl)-5-hydroxy-3,10-diazabicyclo[5.3.0]deca-1(7),5,8-trien-2-one

Pathway: Alkaloids Superclass: Histidine alkaloids Class: Imidazole alkaloids

Chemical Structure

Structure of 6-(2-amino-4-oxo-1H,5H-imidazol-5-yl)-5-hydroxy-3,10-diazabicyclo[5.3.0]deca-1(7),5,8-trien-2-one

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Source Information

Stylissa massa (NA)

Kingdom Metazoa Phylum Porifera Class Demospongiae Order Axinellida Family Axinellidae Genus Stylissa Species Stylissa massa

South China Sea

DOI: 10.3390/md20070454 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

261.2 Da

Threshold ≤ 500

ALogP

-1.16

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C11H11N5O3

Molecular Weight:

261.2410 Da

SMILES:

NC1=NC(=O)C(C2=C(O)CNC(=O)c3[nH]ccc32)N1

InChIKey:

                        NASDRQFHACERHL-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C11H11N5O3/c12-11-15-8(10(19)16-11)6-4-1-2-13-7(4)9(18)14-3-5(6)17/h1-2,8,13,17H,3H2,(H,14,18)(H3,12,15,16,19)

Calculated Properties

ALogP:

-1.160 lipophilicity

TPSA:

132.60 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (1 aromatic)

Chiral Centers:

Fsp³:

0.1818 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006453

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
Enzyme inhibition	IC50	aldose reductase (ALR2)	— Structured numeric value is not available in this record; see the primary reference.	10.3390/md20070454 Marine Drugs

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