SCS-C000243

notoamide X

Pathway: Alkaloids | Amino acids and Peptides Superclass: Peptide alkaloids Class: Indole diketopiperazine alkaloids (L-Trp, L-Pro)

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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.

Download: SDF SMILES

Source Information

Aspergillus ochraceus (fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus ochraceus

South China Sea

DOI: 10.1039/c9ra03640g · RSC Advances

Drug-likeness (Lipinski Ro5)

Molecular Weight

461.5 Da

Threshold ≤ 500

ALogP

2.79

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C26H27N3O5

Molecular Weight:

461.5000 Da

SMILES:

CC1(C)C=Cc2c(ccc3c4c(n(O)c23)C(C)(C)[C@@H]2C[C@]35CCCN3C(=O)[C@]2(NC5=O)C4=O)O1

InChIKey:

                        WUZAONONDREMBU-MEMLUFBQSA-N
                        
                    

InChI:

InChI=1S/C26H27N3O5/c1-23(2)10-8-13-15(34-23)7-6-14-17-19(29(33)18(13)14)24(3,4)16-12-25-9-5-11-28(25)22(32)26(16,20(17)30)27-21(25)31/h6-8,10,16,33H,5,9,11-12H2,1-4H3,(H,27,31)/t16-,25-,26+/m0/s1

Calculated Properties

ALogP:

2.786 lipophilicity

TPSA:

100.87 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (2 aromatic)

Chiral Centers:

Fsp³:

0.5000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000243

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

Indole diketopiperazine alkaloids (L-Trp, L-Pro)

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
Antitumor	IC50	hepatocellular carcinoma cell lines	0.42–3.39 μM	10.1039/c9ra03640g RSC Advances

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