neocarzinostatin chromophore
CHEBI:29655 EXACT SEEDED enzyme inhibitor
A naphthoate ester obtained by formal condensation of the carboxy group of 2-hydroxy-7-methoxy-5-methyl-1-naphthoic acid with the 5-hydroxy group of (1aS,5R,6R,6aE,9aR)-5-hydroxy-1a-[(4R)-2-oxo-1,3-dioxolan-4-yl]-2,3,8,9-tetradehydro-1a,5,6,9a-tetrahydrocyclopenta[5,6]cyclonona[1,2-b]oxiren-6-yl 2,6-dideoxy-2-(methylamino)-α-D-galactopyranoside. The chromophoric part of neocarzinostatin, it is tightly and non-covelently bound to a 113-membered apoprotein, which serves to protect it and release it to the target DNA.
Structure
| Standard InChIKey | QZGIWPZCWHMVQL-UIYAJPBUSA-N |
|---|---|
| SMILES | C[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)O[C@H]\2[C@@H](C=C3/C2=C\C#C[C@@H]4[C@@](O4)(C#C3)[C@H]5COC(=O)O5)OC(=O)C6=C(C=CC7=C(C=C(C=C76)OC)C)O)NC)O)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:447545 |
Filing pathway
Unclassified — 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 pks, 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 carzinostaticus subsp. neocarzinostaticus NCBITaxon:167636 |
BGC_CHARACTERIZED | mibig:BGC0000112 | PMID:15797213 |
Occurrences 1
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 carzinostaticus NCBITaxon:167636 |
LOTUS | DOI:10.1021/JA00191A028 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000112 | Streptomyces carzinostaticus subsp. neocarzinostaticus NCBITaxon:167636 |
CLUSTER_DEMONSTRATED | genbank:AY117439.1 |
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 2
| Assay | Result | Reference |
|---|---|---|
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 0.0001 uM | PMID:15640161 |
| Experimentally measured binding affinity data derived from PDB | ACTIVE | PMID:15640161 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000112 | MIBIG | 5 |
| CHEBI:29655 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/neocarzinostatin-chromophore.yaml, which is generated from the committed inventories. Neither is edited by hand.