SCS-C000244

notoamide Y

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

477.2 Da

Threshold ≤ 500

ALogP

2.37

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H31N3O5

Molecular Weight:

477.2300 Da

SMILES:

CO[C@@H]1[C@@]23NC(=O)[C@]4(CCCN4C2=O)C[C@H]3C(C)(C)[C@]12C(=O)Nc1c2ccc2c1C=CC(C)(C)O2

InChIKey:

                        KYOGJHMTXUTNJJ-WDMQBYORSA-N
                        
                    

InChI:

InChI=1S/C27H31N3O5/c1-23(2)11-9-14-16(35-23)8-7-15-18(14)28-21(32)26(15)19(34-5)27-17(24(26,3)4)13-25(20(31)29-27)10-6-12-30(25)22(27)33/h7-9,11,17,19H,6,10,12-13H2,1-5H3,(H,28,32)(H,29,31)/t17-,19-,25-,26-,27+/m0/s1

Calculated Properties

ALogP:

2.365 lipophilicity

TPSA:

96.97 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-C000244

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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