SCS-C007452
cyclo(ζ6a'-(α,ζα-dimethylallyl)-L-Trp-L-Trp)
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids
Class: Indole diketopiperazine alkaloids (L-Trp, L-Trp)
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
Penicillium brefeldianum GXIMD 02511
(NA)
Original source name: Penicillium brefeldianum | Penicillium brefeldianum GXIMD 02511
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium brefeldianum
South China Sea
DOI:
10.1021/acs.jnatprod.5c00425
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
454.6 Da
Threshold ≤ 500
ALogP
4.17
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C28H30N4O2
Molecular Weight:
454.5740 Da
SMILES:
C=CC(C)(C)Cc1[nH]c2ccccc2c1C[C@@H]1NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC1=O
InChIKey:
VCKBKFARXZFEED-ZEQRLZLVSA-N
InChI:
InChI=1S/C28H30N4O2/c1-4-28(2,3)15-25-20(19-10-6-8-12-22(19)30-25)14-24-27(34)31-23(26(33)32-24)13-17-16-29-21-11-7-5-9-18(17)21/h4-12,16,23-24,29-30H,1,13-15H2,2-3H3,(H,31,34)(H,32,33)/t23-,24-/m0/s1
Calculated Properties
ALogP:
4.172 lipophilicity
TPSA:
89.78 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
2
Rotatable Bonds:
7
Ring Count:
5
(4 aromatic)
Chiral Centers:
2
Fsp³:
0.2857 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007452
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Peptide alkaloids
NPClassifier Class:
Indole diketopiperazine alkaloids (L-Trp, L-Trp)
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 |
|---|---|---|---|---|
| Anti-inflammatory | inhibitory activity | NF-κB | Compounds 1, 2, 4?9, 11?13, 16, 17, 19, and 21?23 exhibited potent inhibitions on NF-κB activation at 20 μM | 10.1021/acs.jnatprod.5c00425 Journal of Natural Products |