validamycin A
CHEBI:29703 EXACT SEEDED antifungal
A member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its β-D-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group. It is the major validamycin produced by Streptomyces hygroscopicus.
Structure
| Standard InChIKey | JARYYMUOCXVXNK-CSLFJTBJSA-N |
|---|---|
| SMILES | C1[C@@H]([C@H]([C@@H]([C@H]([C@H]1N[C@H]2C=C([C@H]([C@@H]([C@H]2O)O)O)CO)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO |
| Stereochemistry | fully defined |
| Cross-references | pubchem:443629 |
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 1
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 |
|---|---|---|---|
| Streptomyces hygroscopicus subsp. yingchengensis NCBITaxon:228732 |
SOURCE_ASSERTION | mibig:BGC0000701 | PMID:16680521 |
Occurrences 24
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 hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1007/0-387-28822-8_2 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1007/S00253-008-1711-Z |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1007/S00253-014-5943-9 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1007/S00253-017-8165-0 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1007/S00449-012-0707-3 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1007/S00449-012-0718-0 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1007/S10482-006-9058-X |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1016/J.BIORTECH.2010.08.114 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1016/J.BIORTECH.2012.03.124 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1016/J.BIORTECH.2017.10.012 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1016/J.GENE.2005.12.035 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1016/J.GENE.2007.02.015 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1016/J.JBIOSC.2016.05.007 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1016/J.JBIOTEC.2009.04.015 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1016/J.JBIOTEC.2015.12.010 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1016/J.YMBEN.2011.10.001 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1021/JA00245A061 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1099/MIC.0.076901-0 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.1128/AEM.71.9.5066-5076.2005 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.7164/ANTIBIOTICS.40.329 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
LOTUS | DOI:10.7164/ANTIBIOTICS.41.1488 |
| Streptomyces hygroscopicus NCBITaxon:1912 |
CHEBI | PMID:5549382 |
| Streptomyces lividans NCBITaxon:1916 |
LOTUS | DOI:10.1016/J.GENE.2007.02.015 |
| Streptomyces hygroscopicus subsp. limoneus NCBITaxon:264445 |
CHEBI | PMID:22961651 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000701 | Streptomyces hygroscopicus subsp. yingchengensis NCBITaxon:228732 |
CLUSTER_UNSTATED | genbank:DQ160226.1 |
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.
Elsewhere in the fleet
- AntibioticMech — CHEBI:29703 (same structure, same inchikey)
Open questions 1
name-disagreement — ChEBI calls this structure 'validamycin A' and MIBiG calls it 'jinggangmycin'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000701 | MIBIG | 5 |
| CHEBI:29703 | CHEBI | 3-star |
This page is generated from data/natural_products/carbohydrates/validamycin-a.yaml, which is generated from the committed inventories. Neither is edited by hand.