115439-61-7
AlkaPlorer ID: AK026675
Synonym: 'Discorhabdin B', '(+)-Discorhabdin B'
IUPAC Name: (1S,14S)-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),8,10,16,19-heptaen-18-one
Structure
SMILES: O=C1C=C2S[C@H]3C[C@]2(C=C1Br)C1=C(N3)C(=O)C2=C3C1=NCCC3=CN2
InChI: InChI=1S/C18H12BrN3O2S/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/h3-4,6,11,21-22H,1-2,5H2/t11-,18-/m0/s1
InChIKey: SVKKMXJIWIOCJC-VOJFVSQTSA-N
Reference
Discorhabdins I and L, Cytotoxic Alkaloids from the Sponge <i>Latrunculia </i><i>b</i><i>revis</i>
LOTUS: LTS0083945
NPASS: NPC225622
data_source: manually
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| None | Sceptrella | Latrunculiidae | Poecilosclerida | Demospongiae | Porifera | Metazoa | Eukaryota |
| Hypomyces odoratus | Hypomyces | Hypocreaceae | Hypocreales | Sordariomycetes | Ascomycota | Fungi | Eukaryota |
| Ageratina aromatica | Ageratina | Asteraceae | Asterales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
Properties Information
Molecule Weight: 414.28400000000016
TPSA？: 74.32
MolLogP？: 2.6083000000000007
Number of H-Donors: 2
Number of H-Acceptors: 5
RingCount: 6
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Bacillus subtilis | Bacillus subtilis | IZ | 6.0 | mM | 10.1016/j.bmcl.2005.12.081 |
| Bacillus subtilis | Bacillus subtilis | MIC | 12.5 | ug.mL-1 | 10.1021/np9005629 |
| Escherichia coli | Escherichia coli | IZ | 1.0 | mM | 10.1016/j.bmcl.2005.12.081 |
| Escherichia coli | Escherichia coli | MIC | 100.0 | ug.mL-1 | 10.1021/np9005629 |
| Homo sapiens | 786-0 | GI50 | 883.08 | nM | None |
| Homo sapiens | A498 | GI50 | 5649.37 | nM | None |
| Homo sapiens | A549 | GI50 | 2471.72 | nM | None |
| Homo sapiens | ACHN | GI50 | 632.41 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 1686.55 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 233.88 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 72.11 | nM | None |
| Homo sapiens | DLD-1 | GI50 | 616.6 | nM | None |
| Homo sapiens | DMS-114 | GI50 | 196.34 | nM | None |
| Homo sapiens | DMS-273 | GI50 | 1166.81 | nM | None |
| Homo sapiens | DU-145 | GI50 | 1918.67 | nM | None |
| Homo sapiens | EKVX | GI50 | 1682.67 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 2296.15 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 102.57 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 744.73 | nM | None |
| Homo sapiens | HL-60 | GI50 | 85.31 | nM | None |
| Homo sapiens | HOP-18 | GI50 | 1782.38 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 972.75 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 1499.68 | nM | None |
| Homo sapiens | HT-29 | GI50 | 344.35 | nM | None |
| Homo sapiens | Hypoxia-inducible factor 1 alpha | IC50 | 3700.0 | nM | 10.1021/acs.jnatprod.5b00846 |
| Homo sapiens | Hypoxia-inducible factor 1 alpha | INH | 0.1 | uM | 10.1021/acs.jnatprod.5b00846 |
| Homo sapiens | Hypoxia-inducible factor 1 alpha | INH | 1.0 | uM | 10.1021/acs.jnatprod.5b00846 |
| Homo sapiens | Hypoxia-inducible factor 1 alpha | Inhibition | nan | % | 10.1021/acs.jnatprod.5b00846 |
| Homo sapiens | IGROV-1 | GI50 | 1531.09 | nM | None |
| Homo sapiens | K562 | GI50 | 208.93 | nM | None |
| Homo sapiens | K562 | IC50 | 7200.0 | nM | 10.1021/np9005629 |
| Homo sapiens | KM12 | GI50 | 1599.56 | nM | None |
| Homo sapiens | KM-20L2 | GI50 | 463.45 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 346.74 | nM | None |
| Homo sapiens | LXFL 529 | GI50 | 189.67 | nM | None |
| Homo sapiens | M14 | GI50 | 726.11 | nM | None |
| Homo sapiens | M19-MEL | GI50 | 232.27 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 115.35 | nM | None |
| Homo sapiens | MCF7 | GI50 | 520.0 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 304.79 | nM | None |
| Homo sapiens | MDA-MB-435 | GI50 | 157.76 | nM | None |
| Homo sapiens | MDA-N | GI50 | 165.2 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 147.91 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 205.12 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 2243.88 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 1221.8 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 2985.38 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 3047.89 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 272.9 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 346.74 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 218.27 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 1853.53 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 540.75 | nM | None |
| Homo sapiens | PC-3 | GI50 | 1828.1 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 304.79 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 272.27 | nM | None |
| Homo sapiens | SF-268 | GI50 | 1541.7 | nM | None |
| Homo sapiens | SF-295 | GI50 | 1503.14 | nM | None |
| Homo sapiens | SF-539 | GI50 | 1625.55 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 468.81 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 1402.81 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 1037.53 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 5623.41 | nM | None |
| Homo sapiens | SN12C | GI50 | 1230.27 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 12445.15 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 1552.39 | nM | None |
| Homo sapiens | SNB-78 | GI50 | 1778.28 | nM | None |
| Homo sapiens | SR | GI50 | 2691.53 | nM | None |
| Homo sapiens | SW-620 | GI50 | 85.7 | nM | None |
| Homo sapiens | T47D | GI50 | 283.14 | nM | None |
| Homo sapiens | TK-10 | GI50 | 1399.59 | nM | None |
| Homo sapiens | U-251 | GI50 | 1753.88 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 213.3 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 554.63 | nM | None |
| Homo sapiens | UO-31 | GI50 | 1570.36 | nM | None |
| Homo sapiens | XF498 | GI50 | 1422.33 | nM | None |
| Micrococcus luteus | Micrococcus luteus | MIC | 25.0 | ug.mL-1 | 10.1021/np9005629 |
| Mus musculus | P388 | IC50 | 0.044 | ug.mL-1 | 10.1016/j.bmcl.2005.12.081 |
| Proteus vulgaris | Proteus vulgaris | MIC | 3.125 | ug.mL-1 | 10.1021/np9005629 |
| Salmonella enterica | Salmonella enterica | MIC | 100.0 | ug.mL-1 | 10.1021/np9005629 |
| Staphylococcus aureus | Sortase A | IC50 | 131700.0 | nM | 10.1021/np9005629 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 50.0 | ug.mL-1 | 10.1021/np9005629 |
| None | NON-PROTEIN TARGET | IC50 | 1800.0 | nM | 10.1021/acs.jnatprod.5b00846 |
| None | NON-PROTEIN TARGET | IC50 | 3100.0 | nM | 10.1021/acs.jnatprod.5b00846 |
| None | NON-PROTEIN TARGET | IC50 | 7000.0 | nM | 10.1021/acs.jnatprod.5b00846 |