SCS-C000056

cyclo L-Trp-L-Phe

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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 hiratsukae SCSIO 7S2001 (SCSIO 7S2001)

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

South China Sea

DOI: 10.3390/md20010071 · Marine Drugs

Aspergillus versicolor (coral-associated fungus)

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

South China Sea · -20m · 112°20′E,16°50′N

DOI: 10.1007/s00449-010-0464-0 · Bioprocess and Biosystems Engineering

Drug-likeness (Lipinski Ro5)

Molecular Weight

333.0 Da

Threshold ≤ 500

ALogP

1.94

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C20H19N3O2

Molecular Weight:

333.0000 Da

SMILES:

O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N[C@H]1Cc1ccccc1

InChIKey:

                        CUVKAUWOMPJEMI-ROUUACIJSA-N
                        
                    

InChI:

InChI=1S/C20H19N3O2/c24-19-17(10-13-6-2-1-3-7-13)22-20(25)18(23-19)11-14-12-21-16-9-5-4-8-15(14)16/h1-9,12,17-18,21H,10-11H2,(H,22,25)(H,23,24)/t17-,18-/m0/s1

Calculated Properties

ALogP:

1.936 lipophilicity

TPSA:

73.99 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (3 aromatic)

Chiral Centers:

Fsp³:

0.2000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000056

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids Small peptides

NPClassifier Class:

Dipeptides Indole diketopiperazine alkaloids (L-Trp, L-Trp) Other indole diketopiperazine alkaloids Simple diketopiperazine 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
Antitumor	IC50	human tumor cell lines	3.3 μg/mL	10.1007/s00449-010-0464-0 Bioprocess and Biosystems Engineering

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