SCS-C006767
roquefortine C
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Histidine alkaloids | Peptide alkaloids
Class: Imidazole alkaloids | Other indole diketopiperazine alkaloids
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
Penicillium sp.
(soft coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
NA
South China Sea
DOI:
10.1177/1934578x1300800313
· Natural Product Communications
Drug-likeness (Lipinski Ro5)
Molecular Weight
389.5 Da
Threshold ≤ 500
ALogP
2.38
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H23N5O2
Molecular Weight:
389.4590 Da
SMILES:
C=CC(C)(C)[C@@]12C[C@H]3C(=O)N/C(=C/c4cnc[nH]4)C(=O)N3[C@@H]1Nc1ccccc12
InChIKey:
SPWSUFUPTSJWNG-JJUKSXGLSA-N
InChI:
InChI=1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+/t17-,20-,22+/m0/s1
Calculated Properties
ALogP:
2.383 lipophilicity
TPSA:
90.12 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
4
Rotatable Bonds:
3
Ring Count:
5
(2 aromatic)
Chiral Centers:
3
Fsp³:
0.3182 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006767
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Histidine alkaloids
Peptide alkaloids
NPClassifier Class:
Imidazole alkaloids
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 |
|---|---|---|---|---|
| Antifouling | inhibition of larval settlement | Balanus amphitrite | 7.0 μg/mL | 10.1177/1934578x1300800313 Natural Product Communications |
| Antifouling | inhibition of larval settlement | Bugula neritina | 2.1 μg/mL | 10.1177/1934578x1300800313 Natural Product Communications |