tobramycin
CHEBI:28864 EXACT SEEDED antibacterialenzyme inhibitor
A amino cyclitol glycoside that is kanamycin B lacking the 3-hydroxy substituent from the 2,6-diaminoglucose ring.
Structure
| Standard InChIKey | NLVFBUXFDBBNBW-PBSUHMDJSA-N |
|---|---|
| SMILES | C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H](C[C@@H]([C@H](O3)CN)O)N)N |
| Stereochemistry | fully defined |
| Cross-references | pubchem:36294 |
Filing pathway
Carbohydrates — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is saccharide, from MIBiG.
Producer organisms 3
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Streptoalloteichus hindustanus NCBITaxon:2017 |
SOURCE_ASSERTION | mibig:BGC0000719 | PMID:16915821 |
| Streptoalloteichus tenebrarius NCBITaxon:1933 |
SOURCE_ASSERTION | mibig:BGC0000720 | PMID:14757238 |
| Streptoalloteichus tenebrarius NCBITaxon:1933 |
SOURCE_ASSERTION | mibig:BGC0000721 | PMID:19362651 |
Occurrences 12
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Streptomyces cremeus NCBITaxon:66881 |
LOTUS | DOI:10.1007/BF00272160 |
| Streptomyces cremeus NCBITaxon:66881 |
LOTUS | DOI:10.1007/BF00327918 |
| Streptomyces cremeus NCBITaxon:66881 |
LOTUS | DOI:10.1007/S00253-010-2908-5 |
| Streptomyces cremeus NCBITaxon:66881 |
LOTUS | DOI:10.1007/S00284-004-4212-Z |
| Streptomyces cremeus NCBITaxon:66881 |
LOTUS | DOI:10.1016/J.BMCL.2004.10.028 |
| Streptomyces cremeus NCBITaxon:66881 |
LOTUS | DOI:10.1016/S0378-1097(03)00881-4 |
| Streptomyces cremeus NCBITaxon:66881 |
LOTUS | DOI:10.1023/B:BILE.0000007063.66429.90 |
| Streptomyces cremeus NCBITaxon:66881 |
LOTUS | DOI:10.1038/JA.2008.111 |
| Streptomyces cremeus NCBITaxon:66881 |
LOTUS | DOI:10.7164/ANTIBIOTICS.45.1167 |
| Aspergillus fumigatus NCBITaxon:746128 |
LOTUS | DOI:10.1021/ACS.JNATPROD.8B00382 |
| Serratia plymuthica NCBITaxon:82996 |
LOTUS | DOI:10.1021/ACS.JNATPROD.7B00565 |
| Streptoalloteichus hindustanus NCBITaxon:2017 |
LOTUS | DOI:10.1038/JA.2006.51 |
Biosynthetic gene clusters 3
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000719 | Streptoalloteichus hindustanus NCBITaxon:2017 |
CLUSTER_UNSTATED | genbank:AB103327.1 |
| mibig:BGC0000720 | Streptoalloteichus tenebrarius NCBITaxon:1933 |
CLUSTER_UNSTATED | genbank:AJ579650.1 |
| mibig:BGC0000721 | Streptoalloteichus tenebrarius NCBITaxon:1933 |
CLUSTER_UNSTATED | genbank:AJ810851.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Bioactivities 14
| Assay | Result | Reference |
|---|---|---|
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell line | 7.4219 uM | pubchem.aid:2202236 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell line | 20.9177 uM | pubchem.aid:2202237 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell line | 23.47 uM | pubchem.aid:2202234 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 0.7943 uM | pubchem.aid:1645887 |
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 0.7943 uM | pubchem.aid:1645887 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | 18.6429 uM | pubchem.aid:1963824 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | 18.6429 uM | pubchem.aid:1963824 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells | 2.9547 uM | pubchem.aid:1963823 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells | 2.9547 uM | pubchem.aid:1963823 |
| qHTS assay for small molecule agonists of the p53 signaling pathway - cell viability | 1.0124 uM | pubchem.aid:651633 |
| A screen for compounds that inhibit the activity of LtaS in Staphylococcus aureus | ACTIVE | pubchem.aid:720641 |
| Cell-based high throughput primary assay to identify activators of GPR151 | ACTIVE | pubchem.aid:1508602 |
| DSSTox (FDAMDD) FDA Maximum (Recommended) Daily Dose Database | ACTIVE | pubchem.aid:1195 |
| High Throughput Screen to Identify Inhibitors of Mycobacterium tuberculosis H37Rv | ACTIVE | pubchem.aid:1332 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:28864 (same structure, same inchikey)
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000719, BGC0000720, BGC0000721. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000719 | MIBIG | 5 |
| BGC0000720 | MIBIG | 3 |
| BGC0000721 | MIBIG | 4 |
| CHEBI:28864 | CHEBI | 3-star |
This page is generated from data/natural_products/carbohydrates/tobramycin.yaml, which is generated from the committed inventories. Neither is edited by hand.