SCS-C006110
dihydrocryptoechinulin D
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids
Class: Other indole diketopiperazine alkaloids
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
Eurotium sp. SCSIO F452
(gorgonian-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Eurotium
Species
NA
South China Sea
· 158 m
· 17°29.804'N, 110°0.292'E
DOI:
10.3389/fchem.2019.00350
· Frontiers in Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
621.8 Da
Threshold ≤ 500
ALogP
6.53
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C38H43N3O5
Molecular Weight:
621.7780 Da
SMILES:
C=CC(C)(C)c1[nH]c2ccccc2c1/C=C1\NC(=O)C2(CC(C)C=CC2CCc2c(O)cc(CC=C(C)C)c(O)c2C=O)NC1=O
InChIKey:
DLAMKANDEMZUSS-DXJNIWACSA-N
InChI:
InChI=1S/C38H43N3O5/c1-7-37(5,6)34-28(26-10-8-9-11-30(26)39-34)19-31-35(45)41-38(36(46)40-31)20-23(4)13-15-25(38)16-17-27-29(21-42)33(44)24(18-32(27)43)14-12-22(2)3/h7-13,15,18-19,21,23,25,39,43-44H,1,14,16-17,20H2,2-6H3,(H,40,46)(H,41,45)/b31-19-
Calculated Properties
ALogP:
6.535 lipophilicity
TPSA:
131.52 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
5
Rotatable Bonds:
9
Ring Count:
5
(3 aromatic)
Chiral Centers:
3
Fsp³:
0.3421 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006110
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Peptide alkaloids
NPClassifier Class:
Other indole diketopiperazine alkaloids
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 |
|---|---|---|---|---|
| Antioxidant | IC50 | DPPH radical | — Structured numeric value is not available in this record; see the primary reference. | 10.3389/fchem.2019.00350 Frontiers in Chemistry |
| Antitumor | IC50 | SF-268 tumor cell line | 48.900000000000006–54.5 μM | 10.3389/fchem.2019.00350 Frontiers in Chemistry |
| Antitumor | IC50 | HepG2 tumor cell line | 47.9–51.9 μM | 10.3389/fchem.2019.00350 Frontiers in Chemistry |
| Antitumor | IC50 | SF-268 tumor cell line | 95.5–99.1 μM | 10.3389/fchem.2019.00350 Frontiers in Chemistry |
| Antitumor | IC50 | HepG2 tumor cell line | 97.7–99.7 μM | 10.3389/fchem.2019.00350 Frontiers in Chemistry |