SCS-C008062

asperfatsine E

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

507.7 Da

Threshold ≤ 500

ALogP

4.44

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C30H41N3O4

Molecular Weight:

507.6750 Da

SMILES:

C=CC(C)(C)c1[nH]c2c(C[C@H](O)C(C)(C)OC)c(CC=C(C)C)ccc2c1/C=C1\NC(=O)[C@H](C)NC1=O

InChIKey:

                        DDYTTZAAOYMWQH-BPXFCJCUSA-N
                        
                    

InChI:

InChI=1S/C30H41N3O4/c1-10-29(5,6)26-22(15-23-28(36)31-18(4)27(35)32-23)20-14-13-19(12-11-17(2)3)21(25(20)33-26)16-24(34)30(7,8)37-9/h10-11,13-15,18,24,33-34H,1,12,16H2,2-9H3,(H,31,36)(H,32,35)/b23-15-/t18-,24-/m0/s1

Calculated Properties

ALogP:

4.444 lipophilicity

TPSA:

103.45 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.4667 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008062

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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