SCS-C000018
beauvericin
Pathway: Amino acids and Peptides | Polyketides
Superclass: Oligopeptides
Class: Cyclic peptides | Depsipeptides
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Aspergillus terreus GX7-3B
(mangrove endophytic fungus)
Original source name: Aspergillus terreus (No. GX7-3B)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus terreus
Guangxi coast
DOI:
10.3390/md11072616
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
783.9 Da
Threshold ≤ 500
ALogP
4.91
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C45H57N3O9
Molecular Weight:
783.9000 Da
SMILES:
CC(C)[C@H]1OC(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](Cc2ccccc2)N(C)C1=O
InChIKey:
GYSCAQFHASJXRS-FFCOJMSVSA-N
InChI:
InChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1
Calculated Properties
ALogP:
4.912 lipophilicity
TPSA:
139.83 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
9
Rotatable Bonds:
9
Ring Count:
4
(3 aromatic)
Chiral Centers:
6
Fsp³:
0.4667 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000018
NPClassifier Pathway:
Amino acids and Peptides
Polyketides
NPClassifier Superclass:
Oligopeptides
NPClassifier Class:
Cyclic peptides
Depsipeptides
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
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 |
|---|---|---|---|---|
| Enzyme inhibition | IC50 | AChE | 3.09 μM | 10.3390/md11072616 Marine Drugs |
| Antitumor | IC50 | MCF-7 | 2.02 μM | 10.3390/md11072616 Marine Drugs |
| Antitumor | IC50 | A549 | 0.82 μM | 10.3390/md11072616 Marine Drugs |
| Antitumor | IC50 | Hela | 1.14 μM | 10.3390/md11072616 Marine Drugs |
| Antitumor | IC50 | KB | 1.1 μM | 10.3390/md11072616 Marine Drugs |