SCS-C008340

Tagpyrrollin A

Pathway: Alkaloids

Chemical Structure

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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.

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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: 10.1021/acs.orglett.4c01976 · Organic Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight

343.3 Da

Threshold ≤ 500

ALogP

-0.86

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C16H17N5O4

Molecular Weight:

343.3430 Da

SMILES:

O=C1NCC/C(=C2/N=C3NC4CC(C(O)CO4)N3C2=O)c2cc[nH]c21

InChIKey:

                        RINJKJVZVGASJA-JYRVWZFOSA-N
                        
                    

InChI:

InChI=1S/C16H17N5O4/c22-10-6-25-11-5-9(10)21-15(24)13(20-16(21)19-11)8-2-4-18-14(23)12-7(8)1-3-17-12/h1,3,9-11,17,22H,2,4-6H2,(H,18,23)(H,19,20)/b13-8-

Calculated Properties

ALogP:

-0.863 lipophilicity

TPSA:

119.05 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (1 aromatic)

Chiral Centers:

Fsp³:

0.4375 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008340

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

N/A

NPClassifier Class:

N/A

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	enzyme inhibition	AKR1B1 (aldose reductase)	9.6 μM	10.1021/acs.orglett.4c01976 Organic Letters
Enzyme inhibition	binding affinity	AKR1B1	3.4 μM	10.1021/acs.orglett.4c01976 Organic Letters

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