264624-39-7
AlkaPlorer ID: AK009146
Synonym: '(+)-cis-3,4-Dihydrohamacanthin B', 'cis-3,4-Dihydrohamacanthin B'
IUPAC Name: (3S,5R)-3,5-bis(6-bromo-1H-indol-3-yl)piperazin-2-one
Structure
SMILES: OC1=NC[C@@H](C2=CNC3=CC(Br)=CC=C23)N[C@H]1C1=CNC2=CC(Br)=CC=C12
InChI: InChI=1S/C20H16Br2N4O/c21-10-1-3-12-14(7-23-16(12)5-10)18-9-25-20(27)19(26-18)15-8-24-17-6-11(22)2-4-13(15)17/h1-8,18-19,23-24,26H,9H2,(H,25,27)/t18-,19-/m0/s1
InChIKey: OXVVLWOQGFZGEO-OALUTQOASA-N
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| None | Spongosorites | Halichondriidae | Suberitida | Demospongiae | Porifera | Metazoa | Eukaryota |
| None | Spongosorites | Halichondriidae | Suberitida | Demospongiae | Porifera | Metazoa | Eukaryota |
Properties Information
Molecule Weight: 488.1830000000001
TPSA？: 76.2
MolLogP？: 5.516300000000002
Number of H-Donors: 4
Number of H-Acceptors: 2
RingCount: 5
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Enterococcus faecalis | Enterococcus faecalis | MIC | 40.0 | ug.mL-1 | 10.1016/j.bmcl.2016.08.095 |
| Enterococcus faecium | Enterococcus faecium | MIC | 25.0 | ug.mL-1 | 10.1021/np049577a |
| Escherichia coli | Escherichia coli | MIC | 25.0 | ug.mL-1 | 10.1021/np049577a |
| Escherichia coli | Escherichia coli | MIC | 40.0 | ug.mL-1 | 10.1016/j.bmcl.2016.08.095 |
| Homo sapiens | A549 | ED50 | 3.41 | ug ml-1 | 10.1021/np049577a |
| Homo sapiens | HCT-15 | ED50 | 2.83 | ug ml-1 | 10.1021/np049577a |
| Homo sapiens | SK-MEL-2 | ED50 | 3.85 | ug ml-1 | 10.1021/np049577a |
| Homo sapiens | SK-OV-3 | ED50 | 3.62 | ug ml-1 | 10.1021/np049577a |
| Homo sapiens | XF498 | ED50 | 3.22 | ug ml-1 | 10.1021/np049577a |
| Klebsiella oxytoca | Klebsiella oxytoca | MIC | 25.0 | ug.mL-1 | 10.1021/np049577a |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | MIC | 25.0 | ug.mL-1 | 10.1021/np049577a |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 6.25 | ug.mL-1 | 10.1021/np500755v |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 10.0 | ug.mL-1 | 10.1016/j.bmcl.2016.08.095 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 12.5 | ug.mL-1 | 10.1016/j.bmc.2014.01.020 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 12.5 | ug.mL-1 | 10.1016/j.bmc.2019.07.023 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 12.5 | ug.mL-1 | 10.1016/j.ejmech.2016.09.018 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 12.5 | ug.mL-1 | 10.1021/np049577a |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 12.5 | ug.mL-1 | 10.1021/np500755v |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 16.0 | nM | 10.1016/j.ejmech.2020.112945 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 20.0 | ug.mL-1 | 10.1016/j.bmcl.2016.08.095 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 25.0 | ug.mL-1 | 10.1021/np049577a |
| Staphylococcus aureus (strain MRSA252) | Pyruvate kinase | IC50 | 16.0 | nM | 10.1016/j.ejmech.2016.09.018 |
| Staphylococcus aureus (strain MRSA252) | Pyruvate kinase | IC50 | 16.0 | nM | 10.1021/jm500373x |
| Streptococcus pyogenes | Streptococcus pyogenes | MIC | 12.5 | ug.mL-1 | 10.1021/np049577a |
| Streptococcus pyogenes | Streptococcus pyogenes | MIC | 25.0 | ug.mL-1 | 10.1021/np049577a |
| None | Unchecked | IC50 | 16.0 | nM | 10.1016/j.bmc.2014.01.020 |
| None | Unchecked | IC50 | 16.0 | nM | 10.1016/j.bmc.2019.07.023 |
| None | Unchecked | IC50 | 16.0 | nM | 10.1021/np500755v |
| None | Unchecked | IC50 | 5100.0 | nM | 10.1016/j.ejmech.2020.112945 |
| None | Unchecked | Selectivity ratio | 166.0 | None | 10.1016/j.ejmech.2016.09.018 |
| None | Unchecked | Selectivity ratio | 166.0 | None | 10.1021/np500755v |