SCS-C008055

asperfatsine B

Pathway: Amino acids and Peptides Superclass: Oligopeptides Class: Lipopeptides

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

758.1 Da

Threshold ≤ 500

ALogP

10.38

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

2 violations (MW, ALogP) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C47H71N3O5

Molecular Weight:

758.1010 Da

SMILES:

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

InChIKey:

                        BEYPHZHQAICILC-ATDGRXASSA-N
                        
                    

InChI:

InChI=1S/C47H71N3O5/c1-10-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-41(51)55-40(47(8,9)54)32-37-35(28-27-33(3)4)29-30-36-38(43(50-42(36)37)46(6,7)11-2)31-39-45(53)48-34(5)44(52)49-39/h11,18-19,27,29-31,34,40,50,54H,2,10,12-17,20-26,28,32H2,1,3-9H3,(H,48,53)(H,49,52)/b19-18-,39-31-/t34-,40-/m0/s1

Calculated Properties

ALogP:

10.378 lipophilicity

TPSA:

120.52 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.5957 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008055

NPClassifier Pathway:

Amino acids and Peptides

NPClassifier Superclass:

Oligopeptides

NPClassifier Class:

Lipopeptides

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
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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