SCS-C008063

asperfatsine F

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

475.6 Da

Threshold ≤ 500

ALogP

4.60

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C29H37N3O3

Molecular Weight:

475.6330 Da

SMILES:

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

InChIKey:

                        JHLPLABLVPGIIN-HKPSVDRMSA-N
                        
                    

InChI:

InChI=1S/C29H37N3O3/c1-8-29(6,7)26-22(15-23-27(34)31-24(16-33)28(35)30-23)21-14-12-19(11-9-17(2)3)20(25(21)32-26)13-10-18(4)5/h8-10,12,14-15,24,32-33H,1,11,13,16H2,2-7H3,(H,30,35)(H,31,34)/b23-15-/t24-/m0/s1

Calculated Properties

ALogP:

4.597 lipophilicity

TPSA:

94.22 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.3793 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008063

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
Anti-inflammatory	inactivity	Monocyte adhesion to endothelial cells	— Structured numeric value is not available in this record; see the primary reference.	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
Antitumor	—	Human umbilical vein endothelial cells (HUVECs)	whereas the other compounds showed no significant cytotoxicity at a concentration of 20.0 μM (Figure 4A).	10.1021/acs.jnatprod.5c00077 Journal of Natural Products

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