SCS-C006276
variecolorin H
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids
Class: Indole diketopiperazine alkaloids (L-Trp, L-Ala)
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.
Source Information
Aspergillus sp. SCSIO 41407
(coral-derived fungus)
Original source name: Aspergillus sp. SCSIO41407
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
NA
South China Sea
DOI:
10.3390/molecules26164851
· Molecules
Drug-likeness (Lipinski Ro5)
Molecular Weight
353.4 Da
Threshold ≤ 500
ALogP
2.58
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C20H23N3O3
Molecular Weight:
353.4220 Da
SMILES:
C=CC(C)(C)c1[nH]c2ccccc2c1/C=C1\NC(=O)C(C)(OC)NC1=O
InChIKey:
AULFXBHXEZPTRY-PTNGSMBKSA-N
InChI:
InChI=1S/C20H23N3O3/c1-6-19(2,3)16-13(12-9-7-8-10-14(12)21-16)11-15-17(24)23-20(4,26-5)18(25)22-15/h6-11,21H,1H2,2-5H3,(H,22,25)(H,23,24)/b15-11-
Calculated Properties
ALogP:
2.581 lipophilicity
TPSA:
83.22 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
3
Rotatable Bonds:
4
Ring Count:
3
(2 aromatic)
Chiral Centers:
1
Fsp³:
0.3000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006276
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Peptide alkaloids
NPClassifier Class:
Indole diketopiperazine alkaloids (L-Trp, L-Ala)
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 | nuclear factor-κB (NF-κB) | 19.2 μM | 10.3390/molecules26164851 Molecules |
| Bone metabolism / Osteoclast | inhibitory activity | RANKL-induced osteoclast differentiation | 5.0 μM | 10.3390/molecules26164851 Molecules |
| Enzyme inhibition | inhibitory activity | acetylcholinesterase (AChE) | All the isolated compounds (1–15) were evaluated for AChE inhibitory activity. Compounds 3–6 displayed inhibition against AChE | 10.3390/molecules26164851 Molecules |