SCS-C008064

tardiketopiperazine B

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

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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 sp. SCSIO 41034 (coral-derived fungus)

Original source name: Aspergillus sp. SCSIO41034 (isolated from an unidentified sponge species)

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

South China Sea

DOI: 10.1021/acs.jnatprod.5c00077 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

393.5 Da

Threshold ≤ 500

ALogP

3.69

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C24H31N3O2

Molecular Weight:

393.5310 Da

SMILES:

C=CC(C)(C)c1[nH]c2c(CC=C(C)C)cccc2c1C[C@@H]1NC(=O)[C@H](C)NC1=O

InChIKey:

                        QNQMVKRHUCFRIY-KXBFYZLASA-N
                        
                    

InChI:

InChI=1S/C24H31N3O2/c1-7-24(5,6)21-18(13-19-23(29)25-15(4)22(28)26-19)17-10-8-9-16(20(17)27-21)12-11-14(2)3/h7-11,15,19,27H,1,12-13H2,2-6H3,(H,25,29)(H,26,28)/t15-,19-/m0/s1

Calculated Properties

ALogP:

3.686 lipophilicity

TPSA:

73.99 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.4167 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008064

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

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

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	—	HUVECs	20.0 μM	10.1021/acs.jnatprod.5c00077 Journal of Natural Products
Antiviral	inhibitory activity	HSV-1/2, dengue virus, Zika virus	20.0 μM	10.1021/acs.jnatprod.5c00077 Journal of Natural Products
Antitumor	inhibitory activity	PC-3, 22Rv1, A549 cancer cell lines	20.0 μM	10.1021/acs.jnatprod.5c00077 Journal of Natural Products

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