tetracenomycin C

CHEBI:9470 EXACT SEEDED antibacterial

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

Structure

Standard InChIKey	ULHJWHCSSAEMLW-UEVCKROQSA-N
SMILES	O[C@H]1[C@@]2(O)[C@@](C(C(C(O)=C(C(C)=C(C(OC)=O)C(OC)=C4)C4=C3)=C3C2=O)=O)(O)C(C=C1OC)=O
Stereochemistry	fully defined

Filing pathway

Polyketides — 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 glaucescens NCBITaxon:1907	BGC_CHARACTERIZED	mibig:BGC0000275	PMID:1548230

Occurrences 23

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 olivaceus NCBITaxon:47716	LOTUS	DOI:10.1021/NP010007+
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1002/ANGE.19951071525
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1002/ANIE.199505651
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1002/J.1460-2075.1989.TB08414.X
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1007/BF00873025
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1007/S00253-009-2428-3
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1016/0378-1119(91)90588-3
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1016/J.JBIOTEC.2017.09.008
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1016/S0014-5793(98)00840-0
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1016/S1074-5521(97)90233-7
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1021/BI00029A015
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1021/BI00077A019
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1021/BI00092A026
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1021/BI0258804
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1073/PNAS.84.13.4445
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1074/JBC.M406144200
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1099/00221287-113-2-243
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1128/JB.173.20.6475-6483.1991
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1128/JB.174.6.1810-1820.1992
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1128/JB.175.23.7571-7580.1993
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.1128/JB.177.2.477-481.1995
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.3109/14756369209040747
Streptomyces glaucescens NCBITaxon:1907	LOTUS	DOI:10.7164/ANTIBIOTICS.45.1190

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000275	Streptomyces glaucescens NCBITaxon:1907	CLUSTER_DEMONSTRATED	genbank:M80674.1

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.

Biosynthesis curated

Written by a curator with claim-level evidence on each step; not derived from a source. This is what the rest of the record exists to support.

Step	Enzyme	Reaction	Substrate → product	Evidence
2	TcmG tetracenomycin A2 monooxygenase-dioxygenase UniProtKB:P39888	RHEA:42820	CHEBI:32197 → CHEBI:9470	DOI:10.1128/jb.175.12.3876-3886.1993

Step 2: This curates the final Streptomyces glaucescens TcmG-catalyzed triple hydroxylation of tetracenomycin A2 to tetracenomycin C; the preceding TcmP methylation and earlier polyketide assembly steps remain uncurated.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Partial Streptomyces glaucescens tetracenomycin C biosynthesis graph for TcmG-catalyzed triple hydroxylation of tetracenomycin A2.

Subject	Predicate	Object	Notes	Evidence
tetracenomycin A2	is hydroxylated by	TcmG	RHEA:42820 also consumes two NADPH and two O2 molecules in this TcmG-catalyzed terminal oxygenase step.	DOI:10.1128/jb.175.12.3876-3886.1993 DOI:10.1016/s0021-9258(18)43874-4 DOI:10.1021/ol0002267 https://mibig.secondarymetabolites.org/repository/BGC0000275.4/ https://www.uniprot.org/uniprotkb/P39888 https://www.rhea-db.org/rhea/42820 reference DOI:10.1128/jb.175.12.3876-3886.1993 evidence type PRIMARY_EXPERIMENT snippet tcmG is responsible for the hydroxylation of TCM A2 at positions C-4, C-4a, and C-12a to give TCM C notes Decker et al. sequenced the Streptomyces glaucescens M80674 tcmG locus and used heterologous expression to place tcmG in the final tetracenomycin C hydroxylation step. reference DOI:10.1016/s0021-9258(18)43874-4 evidence type PRIMARY_EXPERIMENT snippet The heterologous expression of the tcmG gene in Streptomyces lividans and the purification and characterization of TcmG protein notes Shen and Hutchinson purified TcmG/Tcm A2 oxygenase and measured NADPH-dependent conversion of tetracenomycin A2 toward tetracenomycin C. reference DOI:10.1021/ol0002267 evidence type PRIMARY_EXPERIMENT snippet The TcmG or ElmG oxygenase-catalyzed triple hydroxylation of tetracenomycin (Tcm) A2 to Tcm C notes Rafanan et al. established the monooxygenase-dioxygenase stoichiometry captured by RHEA:42820. reference https://mibig.secondarymetabolites.org/repository/BGC0000275.4/ evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes MIBiG BGC0000275.4 encodes tcmG as GenBank protein AAA67511.1 in the Streptomyces glaucescens M80674.1 tetracenomycin C cluster. reference https://www.uniprot.org/uniprotkb/P39888 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes Reviewed UniProtKB:P39888 is the 561 aa Streptomyces glaucescens TcmG/tetracenomycin A2 monooxygenase-dioxygenase, maps to EMBL M80674 protein AAA67511.1, and annotates RHEA:42820 with physiological left-to-right direction RHEA:42821. reference https://www.rhea-db.org/rhea/42820 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes RHEA:42820 captures tetracenomycin A2 + 2 NADPH + 2 O2 + 2 H(+) = tetracenomycin C + 2 NADP(+) + H2O; local Rhea directions map the left-to-right product-forming reaction to RHEA:42821 and UniProtKB:P39888.
TcmG	forms	tetracenomycin C	RHEA:42821 is the tetracenomycin C-forming physiological direction.	DOI:10.1128/jb.175.12.3876-3886.1993 DOI:10.1016/s0021-9258(18)43874-4 DOI:10.1021/ol0002267 https://mibig.secondarymetabolites.org/repository/BGC0000275.4/ https://www.uniprot.org/uniprotkb/P39888 https://www.rhea-db.org/rhea/42820 reference DOI:10.1128/jb.175.12.3876-3886.1993 evidence type PRIMARY_EXPERIMENT snippet tcmG is responsible for the hydroxylation of TCM A2 at positions C-4, C-4a, and C-12a to give TCM C notes Decker et al. sequenced the Streptomyces glaucescens M80674 tcmG locus and used heterologous expression to place tcmG in the final tetracenomycin C hydroxylation step. reference DOI:10.1016/s0021-9258(18)43874-4 evidence type PRIMARY_EXPERIMENT snippet The heterologous expression of the tcmG gene in Streptomyces lividans and the purification and characterization of TcmG protein notes Shen and Hutchinson purified TcmG/Tcm A2 oxygenase and measured NADPH-dependent conversion of tetracenomycin A2 toward tetracenomycin C. reference DOI:10.1021/ol0002267 evidence type PRIMARY_EXPERIMENT snippet The TcmG or ElmG oxygenase-catalyzed triple hydroxylation of tetracenomycin (Tcm) A2 to Tcm C notes Rafanan et al. established the monooxygenase-dioxygenase stoichiometry captured by RHEA:42820. reference https://mibig.secondarymetabolites.org/repository/BGC0000275.4/ evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes MIBiG BGC0000275.4 encodes tcmG as GenBank protein AAA67511.1 in the Streptomyces glaucescens M80674.1 tetracenomycin C cluster. reference https://www.uniprot.org/uniprotkb/P39888 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes Reviewed UniProtKB:P39888 is the 561 aa Streptomyces glaucescens TcmG/tetracenomycin A2 monooxygenase-dioxygenase, maps to EMBL M80674 protein AAA67511.1, and annotates RHEA:42820 with physiological left-to-right direction RHEA:42821. reference https://www.rhea-db.org/rhea/42820 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes RHEA:42820 captures tetracenomycin A2 + 2 NADPH + 2 O2 + 2 H(+) = tetracenomycin C + 2 NADP(+) + H2O; local Rhea directions map the left-to-right product-forming reaction to RHEA:42821 and UniProtKB:P39888.

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

Elsewhere in the fleet

AntibioticMech — CHEBI:9470 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (tetracenomycin C) ↗ MediaIngredientMech (CHEBI:9470) ↗ TaxonMech: Streptomyces glaucescens (NCBITaxon:1907) ↗ PathwayMech (mibig:BGC0000275) ↗

Provenance

Source concept	Source	Version
BGC0000275	MIBIG	4
CHEBI:9470	CHEBI	3-star

This page is generated from data/natural_products/polyketides/tetracenomycin-c.yaml, which is generated from the committed inventories. Neither is edited by hand.