Discorhabdine A
AlkaPlorer ID: AK008829
Synonym: None
IUPAC Name: (1S,14S,16R)-19-bromo-11-hydroxy-15-thia-4,9,13-triazahexacyclo[12.6.1.13,7.01,16.02,12.010,22]docosa-2(12),3,7(22),8,10,19-hexaen-18-one
Structure
SMILES: O=C1C[C@H]2S[C@H]3C[C@]2(C=C1Br)C1=C(N3)C(=O)C2=C3C1=NCCC3=CN2
InChI: InChI=1S/C18H14BrN3O2S/c19-8-4-18-5-11(25-10(18)3-9(8)23)22-16-13(18)14-12-7(1-2-20-14)6-21-15(12)17(16)24/h4,6,10-11,21-22H,1-3,5H2/t10-,11+,18+/m1/s1
InChIKey: IMRWMDAHKYBDMQ-DDBGAENHSA-N
Reference
Cytotoxic pigments from new zealand sponges of the genus latrunculia : discorhabdins a, b and c
CAS: 112515-41-0
LOTUS: LTS0068524
NPASS: NPC221726
Source
Properties Information
Molecule Weight: 416.3000000000002
TPSA？: 74.32
MolLogP？: 2.4831000000000003
Number of H-Donors: 2
Number of H-Acceptors: 5
RingCount: 6
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Chlorocebus sabaeus | Vero | IC50 | 6800.0 | nM | 10.1021/np900281r |
| Hepacivirus hominis | Hepatitis C virus | EC90 | 10.0 | uM | 10.1021/np900281r |
| Homo sapiens | A549 | IC50 | 0.04 | ug.mL-1 | 10.1021/np50096a015 |
| Homo sapiens | A549 | IC50 | 0.05 | ug.mL-1 | 10.1021/np8007667 |
| Homo sapiens | Endothelin receptor ET-A | Activity | 79.0 | % | 10.1021/np900287e |
| Homo sapiens | Endothelin receptor ET-A | Activity | 100.0 | % | 10.1021/np900287e |
| Homo sapiens | HCT-116 | IC50 | 7.0 | nM | 10.1021/np034084b |
| Homo sapiens | HT-29 | IC50 | 0.01 | ug.mL-1 | 10.1021/np50096a015 |
| Homo sapiens | HT-29 | IC50 | 0.05 | ug.mL-1 | 10.1021/np8007667 |
| Homo sapiens | MDA-MB-231 | IC50 | 0.05 | ug.mL-1 | 10.1021/np8007667 |
| Homo sapiens | Neuropeptide Y receptor type 1 | Activity | 40.0 | % | 10.1021/np900287e |
| Homo sapiens | Neuropeptide Y receptor type 1 | Activity | 90.0 | % | 10.1021/np900287e |
| Mus musculus | Mus musculus | Activity | 25.0 | % | 10.1021/np900281r |
| Mus musculus | Mus musculus | Activity | nan | None | 10.1021/np900281r |
| Mus musculus | P388 | IC50 | 0.1 | ug.mL-1 | 10.1021/np50096a015 |
| Mycobacterium intracellulare | Mycobacterium intracellulare | IC50 | 360.0 | nM | 10.1021/np900281r |
| Mycobacterium intracellulare | Mycobacterium intracellulare | MIC | 740.0 | nM | 10.1021/np900281r |
| Mycobacterium tuberculosis | Mycobacterium tuberculosis | IC50 | nan | None | 10.1021/np900281r |
| Mycobacterium tuberculosis | Mycobacterium tuberculosis | MIC | 7700.0 | nM | 10.1021/np900281r |
| Plasmodium berghei | Plasmodium berghei | Activity | 6.6 | % | 10.1021/np900281r |
| Plasmodium falciparum | Plasmodium falciparum | IC50 | 53.0 | nM | 10.1021/np900281r |
| Staphylococcus aureus | Staphylococcus aureus | IC50 | 4800.0 | nM | 10.1021/np900281r |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 12000.0 | nM | 10.1021/np900281r |
| None | ADMET | Activity | nan | None | 10.1021/np900281r |
| None | NON-PROTEIN TARGET | IC50 | 4.8 | ug.mL-1 | 10.1021/np50096a015 |
| None | Unchecked | Activity | nan | None | 10.1021/np50096a015 |
| None | Unchecked | IC50 | 17.0 | nM | 10.1021/acs.jnatprod.2c00987 |
| None | Unchecked | Ratio IC50 | 130.0 | None | 10.1021/np900281r |