SCS-C006461

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

Pathway: Alkaloids Superclass: Histidine alkaloids Class: Imidazole alkaloids

Chemical Structure

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

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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.

Download: SDF SMILES

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

245.2 Da

Threshold ≤ 500

ALogP

-0.70

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C11H11N5O2

Molecular Weight:

245.2420 Da

SMILES:

NC1=NC(=O)/C(=C2\CCNC(=O)c3[nH]ccc32)N1

InChIKey:

                        JYRJOQGKGMHTOO-VURMDHGXSA-N
                        
                    

InChI:

InChI=1S/C11H11N5O2/c12-11-15-8(10(18)16-11)6-2-4-14-9(17)7-5(6)1-3-13-7/h1,3,13H,2,4H2,(H,14,17)(H3,12,15,16,18)/b8-6-

Calculated Properties

ALogP:

-0.696 lipophilicity

TPSA:

112.37 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-C006461

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
Enzyme inhibition	KD	aldose reductase (ALR2)	12.5 μM	10.3390/md20070454 Marine Drugs

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