SCS-C008269
GKK1032B
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Tetramate alkaloids
Class: Pyrrocidine tetramate 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
Penicillium sp.
(soft coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
NA
South China Sea
DOI:
10.1021/acs.jnatprod.2c00473
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
501.7 Da
Threshold ≤ 500
ALogP
5.15
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C32H39NO4
Molecular Weight:
501.6670 Da
SMILES:
C=C[C@@]1(C)C=C(C)[C@H]2[C@@H]3[C@H](Oc4ccc(cc4)C[C@@H]4C(=O)NC(=O)[C@@H]4C(=O)[C@H]31)[C@@H]1[C@@H](C)C[C@@H](C)C[C@@]12C
InChIKey:
GAPPHVJLWSRLAC-FXHYYJINSA-N
InChI:
InChI=1S/C32H39NO4/c1-7-31(5)15-18(4)24-23-26(31)27(34)22-21(29(35)33-30(22)36)13-19-8-10-20(11-9-19)37-28(23)25-17(3)12-16(2)14-32(24,25)6/h7-11,15-17,21-26,28H,1,12-14H2,2-6H3,(H,33,35,36)/t16-,17+,21+,22+,23+,24+,25+,26+,28+,31+,32-/m1/s1
Calculated Properties
ALogP:
5.151 lipophilicity
TPSA:
72.47 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
4
Rotatable Bonds:
1
Ring Count:
7
(1 aromatic)
Chiral Centers:
11
Fsp³:
0.5938 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008269
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Tetramate alkaloids
NPClassifier Class:
Pyrrocidine tetramate 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 |
|---|---|---|---|---|
| Enzyme inhibition | IC50 | CD45, TCPTP, SHP1, PTP1B | 8.1–17.8 μM | 10.1021/acs.jnatprod.2c00473 Journal of Natural Products |
| Other specified activity | IC50 | LAR | > 200.0 μM | 10.1021/acs.jnatprod.2c00473 Journal of Natural Products |
| Antibacterial | IC50 | six tested pathogens (all or some) | 20.0–50.0 μg/mL | 10.1021/acs.jnatprod.2c00473 Journal of Natural Products |
| Antitumor | IC50 | human lung adenocarcinoma cell line H1975 | >= 10.0 μM | 10.1021/acs.jnatprod.2c00473 Journal of Natural Products |