SCS-C000245

notoamide Z

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

493.6 Da

Threshold ≤ 500

ALogP

1.96

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H31N3O6

Molecular Weight:

493.6000 Da

SMILES:

CO[C@@H]1[C@@]23NC(=O)[C@]4(CCCN4C2=O)C[C@H]3C(C)(C)C2=[N+]([O-])c3c(ccc4c3C=CC(C)(C)O4)[C@]21O

InChIKey:

                        RGEKCJWSPYJSNC-ZUZRYDNBSA-N
                        
                    

InChI:

InChI=1S/C27H31N3O6/c1-23(2)11-9-14-16(36-23)8-7-15-18(14)30(34)19-24(3,4)17-13-25-10-6-12-29(25)22(32)26(17,28-21(25)31)20(35-5)27(15,19)33/h7-9,11,17,20,33H,6,10,12-13H2,1-5H3,(H,28,31)/t17-,20+,25-,26+,27-/m0/s1

Calculated Properties

ALogP:

1.959 lipophilicity

TPSA:

114.17 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (1 aromatic)

Chiral Centers:

Fsp³:

0.5926 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000245

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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