SCS-C001927

(9S,10R,9'S,10'R)-nakamuric acid

Pathway: Alkaloids Superclass: Proline alkaloids Class: Pyrrole alkaloids

Chemical Structure

Structure of (9S,10R,9'S,10'R)-nakamuric acid

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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

Agelas sp. (NA)

Kingdom Metazoa Phylum Porifera Class Demospongiae Order Agelasida Family Agelasidae Genus Agelas Species NA

Yongxing Island

DOI: 10.1016/j.tet.2017.03.078 · Tetrahedron

Drug-likeness (Lipinski Ro5)

Molecular Weight

583.2 Da

Threshold ≤ 500

ALogP

2.06

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

2 violations (MW, HBD) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C20H21Br2N7O4

Molecular Weight:

583.2410 Da

SMILES:

Nc1ncc([C@@H]2[C@@H](CNC(=O)c3cc(Br)c[nH]3)[C@H](CNC(=O)c3cc(Br)c[nH]3)[C@H]2C(=O)O)[nH]1

InChIKey:

                        SJXLCFWCEINREE-KUDNYVPYSA-N
                        
                    

InChI:

InChI=1S/C20H21Br2N7O4/c21-8-1-12(24-3-8)17(30)26-5-10-11(6-27-18(31)13-2-9(22)4-25-13)16(19(32)33)15(10)14-7-28-20(23)29-14/h1-4,7,10-11,15-16,24-25H,5-6H2,(H,26,30)(H,27,31)(H,32,33)(H3,23,28,29)/t10-,11-,15-,16+/m0/s1

Calculated Properties

ALogP:

2.063 lipophilicity

TPSA:

181.78 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (3 aromatic)

Chiral Centers:

Fsp³:

0.3000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001927

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Proline alkaloids

NPClassifier Class:

Pyrrole 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
Antibacterial	MIC	S. aureus ATCC25923, S. aureus ATCC43300	16.0 μg/mL	10.1016/j.tet.2017.03.078 Tetrahedron

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