SCS-C001363

Neopetrosin B

Pathway: Alkaloids Superclass: Tryptophan alkaloids Class: Carboline alkaloids

Chemical Structure

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Source Information

Neopetrosia chaliniformis (NA)

Kingdom Metazoa Phylum Porifera Class Demospongiae Order Haplosclerida Family Petrosiidae Genus Neopetrosia Species Neopetrosia chaliniformis

Xisha Islands

DOI: 10.1021/acs.jnatprod.2c00292 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

419.4 Da

Threshold ≤ 500

ALogP

-1.77

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (HBD) — borderline drug-like

Chemical Properties

Molecular Formula:

C20H25N3O7

Molecular Weight:

419.4340 Da

SMILES:

C[C@@H]1NC(=O)[C@H](Cc2c([C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[nH]c3ccccc23)NC1=O

InChIKey:

                        AHEQIJBMCDOQAN-CRPATHLLSA-N
                        
                    

InChI:

InChI=1S/C20H25N3O7/c1-8-19(28)23-12(20(29)21-8)6-10-9-4-2-3-5-11(9)22-14(10)18-17(27)16(26)15(25)13(7-24)30-18/h2-5,8,12-13,15-18,22,24-27H,6-7H2,1H3,(H,21,29)(H,23,28)/t8-,12-,13+,15+,16-,17-,18+/m0/s1

Calculated Properties

ALogP:

-1.772 lipophilicity

TPSA:

164.14 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (2 aromatic)

Chiral Centers:

Fsp³:

0.5000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001363

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Tryptophan alkaloids

NPClassifier Class:

Carboline 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
Antifibrotic / Organ protection	—	zebrafish liver	20.0 μM	10.1021/acs.jnatprod.2c00292 Journal of Natural Products

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