neocarzinostatin chromophore

CHEBI:29655 EXACT SEEDED enzyme inhibitor

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

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.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 2 nodes, 1 edge

Neocarzinostatin chromophore binds the mature Streptomyces carzinostaticus neocarzinostatin apoprotein captured in PDB 1O5P.

Subject	Predicate	Object	Notes	Evidence
neocarzinostatin chromophore	binds	Streptomyces carzinostaticus neocarzinostatin apoprotein	PubChem BioAssay AID 977611 maps this exact Standard InChIKey to a 0.1 nM Kd row for PDB 1O5P chain A; RCSB reports CHR neocarzinostatin chromophore with the record's Standard InChIKey as a 1O5P non-polymer ligand contacting chain A, and SIFTS maps entity 1 chain A to Streptomyces carzinostaticus UniProtKB:P0A3R9 residues 35-147.	DOI:10.1074/jbc.M411579200 DOI:10.2210/pdb1o5p/pdb reference DOI:10.1074/jbc.M411579200 evidence type PRIMARY_EXPERIMENT snippet Solution NMR Structure Investigation for Releasing Mechanism of Neocarzinostatin Chromophore from the Holoprotein notes Takashima et al. solved PDB 1O5P as a holo-neocarzinostatin solution NMR structure. reference DOI:10.2210/pdb1o5p/pdb evidence type DATABASE_ASSERTION notes RCSB PDB identifies 1O5P entity 1 chain A as 113-residue Streptomyces carzinostaticus neocarzinostatin, maps it to UniProtKB:P0A3R9 by SIFTS, and records CHR neocarzinostatin chromophore as the bound non-polymer ligand.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Bioactivities 2

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

Assay	Result	Target enzyme	Source detail
Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	KD 0.0001 uM; ACTIVE	Not recorded	PMID:15640161 assay Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB evidence reference PMID:15640161 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 977611, deposited by Shanghai Institute of Organic Chemistry; assay type Other. Target accession 1O5P_A was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type KD value 0.0001 units uM activity class ENZYME_INHIBITOR
Experimentally measured binding affinity data derived from PDB	ACTIVE	Not recorded	PMID:15640161 assay Experimentally measured binding affinity data derived from PDB evidence reference PMID:15640161 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1811, deposited by Shanghai Institute of Organic Chemistry; assay type Other. Target accession 1O5P_A was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE activity class ENZYME_INHIBITOR

Explore across X-Mech

AntibioticMech (neocarzinostatin chromophore) ↗ MediaIngredientMech (CHEBI:29655) ↗ TaxonMech: Streptomyces carzinostaticus subsp. neocarzinostaticus (NCBITaxon:167636) ↗ PathwayMech (mibig:BGC0000112) ↗

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.