Bactobolin
AlkaPlorer ID: AK005829
Synonym: None
IUPAC Name: (2S)-N-[(3S,4R,4aR,5R,6R)-3-(dichloromethyl)-5,6,8-trihydroxy-3-methyl-1-oxo-4a,5,6,7-tetrahydro-4H-isochromen-4-yl]-2-aminopropanamide
Structure
SMILES: C[C@H](N)C(O)=N[C@@H]1[C@H]2C(=C(O)C[C@@H](O)[C@@H]2O)C(=O)O[C@]1(C)C(Cl)Cl
InChI: InChI=1S/C14H20Cl2N2O6/c1-4(17)11(22)18-10-8-7(5(19)3-6(20)9(8)21)12(23)24-14(10,2)13(15)16/h4,6,8-10,13,19-21H,3,17H2,1-2H3,(H,18,22)/t4-,6+,8-,9-,10+,14-/m0/s1
InChIKey: RBCHRRIVFAIGFI-RGBMRXMBSA-N
Reference
Quorum-Sensing-Regulated Bactobolin Production by <i>Burkholderia thailandensis</i> E264
PubChem CID: 54676871
CAS: 72615-20-4
LOTUS: LTS0010392
{NPAtlas: NPA005764
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| None | Pseudomonas | Pseudomonadaceae | Pseudomonadales | Gammaproteobacteria | Pseudomonadota | None | Bacteria |
Properties Information
Molecule Weight: 383.22800000000007
TPSA？: 145.6
MolLogP？: 0.3317000000000004
Number of H-Donors: 5
Number of H-Acceptors: 7
RingCount: 2
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Acinetobacter baumannii | Acinetobacter baumannii | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Candida albicans | Candida albicans | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Cryptococcus neoformans | Cryptococcus neoformans | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Escherichia coli | Escherichia coli | MIC | 5000.0 | nM | 10.6019/CHEMBL4296183 |
| Homo sapiens | 786-0 | GI50 | 65.46 | nM | None |
| Homo sapiens | A498 | GI50 | 328.85 | nM | None |
| Homo sapiens | A549 | GI50 | 186.64 | nM | None |
| Homo sapiens | ACHN | GI50 | 175.79 | nM | None |
| Homo sapiens | BT-549 | GI50 | 165.2 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 165.58 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 62.09 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 104.95 | nM | None |
| Homo sapiens | DLD-1 | GI50 | 239.88 | nM | None |
| Homo sapiens | DMS-114 | GI50 | 177.83 | nM | None |
| Homo sapiens | DMS-273 | GI50 | 326.59 | nM | None |
| Homo sapiens | DU-145 | GI50 | 181.97 | nM | None |
| Homo sapiens | EKVX | GI50 | 206.54 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 164.06 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 145.21 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 597.04 | nM | None |
| Homo sapiens | HEK293 | CC50 | 396.0 | nM | 10.6019/CHEMBL4296183 |
| Homo sapiens | HL-60 | GI50 | 166.34 | nM | None |
| Homo sapiens | HOP-18 | GI50 | 570.16 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 151.71 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 111.43 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 124.74 | nM | None |
| Homo sapiens | HT-29 | GI50 | 155.24 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 361.41 | nM | None |
| Homo sapiens | K562 | GI50 | 199.53 | nM | None |
| Homo sapiens | KM12 | GI50 | 171.79 | nM | None |
| Homo sapiens | KM-20L2 | GI50 | 262.42 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 94.62 | nM | None |
| Homo sapiens | LXFL 529 | GI50 | 107.65 | nM | None |
| Homo sapiens | M14 | GI50 | 127.94 | nM | None |
| Homo sapiens | M19-MEL | GI50 | 231.74 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 277.97 | nM | None |
| Homo sapiens | MCF7 | GI50 | 145.55 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 155.6 | nM | None |
| Homo sapiens | MDA-MB-435 | GI50 | 248.31 | nM | None |
| Homo sapiens | MDA-N | GI50 | 104.95 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 104.95 | nM | None |
| Homo sapiens | Monoamine oxidase A | Activity | nan | None | 10.1021/jm800656v |
| Homo sapiens | Monoamine oxidase B | Activity | nan | None | 10.1021/jm800656v |
| Homo sapiens | NCI/ADR-RES | GI50 | 3357.38 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 194.54 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 183.23 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 201.37 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 110.92 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 160.32 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 339.63 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 133.35 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 603.95 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 166.72 | nM | None |
| Homo sapiens | PC-3 | GI50 | 231.74 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 190.99 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 170.22 | nM | None |
| Homo sapiens | RXF 631 | GI50 | 289.07 | nM | None |
| Homo sapiens | SF-268 | GI50 | 183.65 | nM | None |
| Homo sapiens | SF-295 | GI50 | 180.3 | nM | None |
| Homo sapiens | SF-539 | GI50 | 229.09 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 221.82 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 234.42 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 128.82 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 271.02 | nM | None |
| Homo sapiens | SN12C | GI50 | 164.44 | nM | None |
| Homo sapiens | SN12K1 | GI50 | 297.17 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 167.11 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 184.93 | nM | None |
| Homo sapiens | SNB-78 | GI50 | 280.54 | nM | None |
| Homo sapiens | SR | GI50 | 77.62 | nM | None |
| Homo sapiens | SW-620 | GI50 | 145.21 | nM | None |
| Homo sapiens | T47D | GI50 | 209.41 | nM | None |
| Homo sapiens | TK-10 | GI50 | 356.45 | nM | None |
| Homo sapiens | U-251 | GI50 | 143.88 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 377.57 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 230.14 | nM | None |
| Homo sapiens | UO-31 | GI50 | 979.49 | nM | None |
| Homo sapiens | XF498 | GI50 | 93.76 | nM | None |
| Klebsiella pneumoniae | Klebsiella pneumoniae | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Mus musculus | P388 | GI50 | 80.72 | nM | None |
| Mus musculus | P388/ADR | GI50 | 302.69 | nM | None |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 1250.0 | nM | 10.6019/CHEMBL4296183 |