SCS-C006462

(4E)-4-(2-amino-4-oxo-1H-imidazol-5-ylidene)-5-methoxy-1,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one

Pathway: Alkaloids Superclass: Histidine alkaloids Class: Imidazole alkaloids

Chemical Structure

Structure of (4E)-4-(2-amino-4-oxo-1H-imidazol-5-ylidene)-5-methoxy-1,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-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

275.3 Da

Threshold ≤ 500

ALogP

-1.07

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C12H13N5O3

Molecular Weight:

275.2680 Da

SMILES:

COC1CNC(=O)c2[nH]ccc2/C1=C1\NC(N)=NC1=O

InChIKey:

                        WDFPZZAIUGWSFU-VQHVLOKHSA-N
                        
                    

InChI:

InChI=1S/C12H13N5O3/c1-20-6-4-15-10(18)8-5(2-3-14-8)7(6)9-11(19)17-12(13)16-9/h2-3,6,14H,4H2,1H3,(H,15,18)(H3,13,16,17,19)/b9-7+

Calculated Properties

ALogP:

-1.071 lipophilicity

TPSA:

121.60 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (1 aromatic)

Chiral Centers:

Fsp³:

0.2500 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006462

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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