SCS-C008058

asperfatsine G

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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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

3.73

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:

CC(C)=CCc1ccc2c(C[C@@H]3NC(=O)[C@H](C)NC3=O)c[nH]c2c1CC=C(C)C

InChIKey:

                        SZWNMDKDCGFDLP-KKSFZXQISA-N
                        
                    

InChI:

InChI=1S/C24H31N3O2/c1-14(2)6-8-17-9-11-20-18(12-21-24(29)26-16(5)23(28)27-21)13-25-22(20)19(17)10-7-15(3)4/h6-7,9,11,13,16,21,25H,8,10,12H2,1-5H3,(H,26,29)(H,27,28)/t16-,21-/m0/s1

Calculated Properties

ALogP:

3.731 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-C008058

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	—	Human umbilical vein endothelial cells (HUVECs)	Compounds 5, 7, and 12 exhibited moderate cytotoxicity to HUVECs after 24 h, whereas the other compounds showed no significant cytotoxicity at a concentration of 20.0 μM.	10.1021/acs.jnatprod.5c00077 Journal of Natural Products
Antiviral	inactivity	dengue virus; Zika virus	However, all tested compounds were inactive to both viruses and cancer cell lines at a concentration of 20.0 μM.	10.1021/acs.jnatprod.5c00077 Journal of Natural Products
Antitumor	inactivity	A549 cancer cells	However, all tested compounds were inactive to both viruses and cancer cell lines at a concentration of 20.0 μM.	10.1021/acs.jnatprod.5c00077 Journal of Natural Products

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