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methymycin

CHEBI:29630 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

A twelve-membered macrolide antibiotic that is biosynthesised by Streptomyces venezuelae.

Structure

Standard InChIKeyHUKYPYXOBINMND-HYUJHOPRSA-N
SMILESCC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@H](C)C[C@@H](C)C(=O)\C=C\[C@]1(C)O
Stereochemistryfully defined
Cross-referencesnpatlas:NPA01238

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, 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.

TaxonBasisClusterEvidence
Streptomyces venezuelae
Strain: ATCC 15439
NCBITaxon:54571		 SOURCE_ASSERTION mibig:BGC0000094
PMID:9770448, DOI:10.1073/pnas.95.21.12111
  • reference
    PMID:9770448
    evidence type
    DATABASE_ASSERTION
    notes
    MIBiG BGC0000094 entry version 5; citation taken from the entry level
  • reference
    DOI:10.1073/pnas.95.21.12111
    evidence type
    CURATOR_INFERENCE
    notes
    Strain context: ATCC 15439. Xue et al. 1998 (PMID:9770448, DOI:10.1073/pnas.95.21.12111) and GenBank AF079138.1 explicitly identify Streptomyces venezuelae ATCC 15439 as the sequenced and genetically characterized methymycin/pikromycin producer strain for BGC0000094. Preserve NCBITaxon:54571 and existing producer/locus evidence grades. See issue #1010. Taxon identity and evidence grade are unchanged; this is not a species-wide experiment. MIBiG source row BGC0000094:1; SHA256 4a66615916a0118fa9dcf7c56119cd2b9791512ce06b442c397ecb0f278675c5. Curator: antigravity; date: 2026-10-22.

Occurrences 19

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.

TaxonSourceReference
Streptomyces
NCBITaxon:1883		 LOTUS DOI:10.1021/JA01605A026
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1002/PRO.2204
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1007/S00253-008-1455-9
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1007/S10295-018-2024-6
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1007/S12272-012-0907-Z
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1016/J.JBIOTEC.2015.12.028
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1016/S0378-1119(00)00560-6
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1016/S0960-894X(98)00553-8
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1016/S1074-5521(98)90293-9
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1021/JA00055A023
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1021/JA974321V
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1021/JA981500J
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1021/JA981782N
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1021/NP010146R
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1073/PNAS.95.21.12111
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1074/JBC.M605478200
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.1128/GENOMEA.00337-16
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.7164/ANTIBIOTICS.30.76
Streptomyces venezuelae
NCBITaxon:54571		 LOTUS DOI:10.7164/ANTIBIOTICS.45.1981

Biosynthetic gene clusters 1

AccessionHostLocus evidenceGenome
mibig:BGC0000094 Streptomyces venezuelae
NCBITaxon:54571 		CLUSTER_DEMONSTRATED genbank:AF079138.1

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.

StepEnzymeReactionSubstrate → productEvidence
1 DesVII macrolide glycosyltransferase
UniProtKB:Q9ZGH7		 RHEA:31627 CHEBI:29461 → CHEBI:29706 DOI:10.1021/ja049967j
2 PikC cytochrome P450 monooxygenase
UniProtKB:O87605		 CHEBI:29706 → CHEBI:29630 DOI:10.1016/S1074-5521(98)90293-9

Step 1: DesVII (UniProtKB:Q9ZGH7, AAC68677.1, AF079762.1:1475..2755, EC 2.4.1.277) functions in an obligate (alpha-beta)3 complex with the auxiliary protein DesVIII (UniProtKB:Q9ZGH8, AAC68676.1, AF079762.1:119..1327) to transfer the D-desosamine moiety from dTDP-alpha-D-desosamine (CHEBI:27948) onto the 12-membered macrolactone aglycone 10-deoxymethynolide (CHEBI:29461) to form 10-deoxymethymycin (YC-17, CHEBI:29706). RHEA:31627 represents the same reaction using the charged ChEBI species CHEBI:63260 and CHEBI:63307.

Step 2: PikC hydroxylates YC-17, ChEBI's 10-deoxymethymycin, at the C-10 position to form methymycin; the same enzyme can instead hydroxylate YC-17 at C-12 to form the neomethymycin congener.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 1 producer (0 causal) 19 cited occurrences BIOSYNTHETIC LOCUS 1 gene cluster 2 curated pathway steps NATURAL PRODUCT methymycin CHEBI:29630 Polyketides TARGETS & BIOACTIVITY 0 molecular targets 0 bioactivities · 1 graph

Causal graph — biosynthesis 8 nodes, 7 edges

Partial Streptomyces venezuelae methymycin biosynthesis graph for DesVII/DesVIII-catalyzed 10-deoxymethynolide glycosylation to 10-deoxymethymycin (YC-17) followed by PikC-catalyzed hydroxylation to methymycin.

SubjectPredicateObjectNotesEvidence
DesVII macrolide glycosyltransferase assembles into DesVII/DesVIII glycosyltransferase complex DesVII (UniProtKB:Q9ZGH7) is the catalytic glycosyltransferase subunit of the Streptomyces venezuelae DesVII/DesVIII (alpha-beta)3 complex.
DOI:10.1021/ja049967j
DOI:10.1021/bi1007657
DOI:10.1016/j.gene.2006.08.021
DOI:10.1073/pnas.95.21.12111
https://www.uniprot.org/uniprotkb/Q9ZGH7
https://www.uniprot.org/uniprotkb/Q9ZGH8
https://www.ncbi.nlm.nih.gov/nuccore/AF079762.1
  • reference
    DOI:10.1021/ja049967j
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    DesVII has already been proven responsible for the coupling of TDP-D-desosamine with both 10-deoxymethynolide and narbonolide in S. venezuelae, and it has was also shown under in vitro conditions to require an additional protein, DesVIII, for full activity
    notes
    Borisova et al. (PMID:15161264) purified Streptomyces venezuelae DesVII and DesVIII and demonstrated in vitro that DesVII requires the auxiliary protein DesVIII to transfer D-desosamine from TDP-D-desosamine onto narbonolide and 10-deoxymethynolide.
  • reference
    DOI:10.1021/bi1007657
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Together, DesVII and DesVIII serve as the glycosylation catalyst necessary to construct the bacterial macrolide antibiotics methymycin, neomethymycin, narbomycin, and pikromycin in Streptomyces venezuelae
    notes
    Borisova and Liu (PMID:20695498) characterized the tight (alpha-beta)3 heterohexameric Streptomyces venezuelae DesVII/DesVIII complex and showed that coexpression and complex formation with DesVIII are required for robust DesVII macrolide glycosyltransferase activity.
  • reference
    DOI:10.1016/j.gene.2006.08.021
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Our results demonstrated that DesVIII is needed to assist the reaction deployed by the glycosyltransferase DesVII in vivo
    notes
    Hong et al. (PMID:17049185) demonstrated by in vivo bioconversion in Streptomyces lividans that DesVIII is required alongside DesVII to glycosylate narbonolide to narbomycin and 10-deoxymethynolide to YC-17.
  • reference
    DOI:10.1073/pnas.95.21.12111
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Dedicated to the biosynthesis of dTDP-D-desosamine, an essential deoxysugar component in the macrolide antibiotics methymycin, neomethymycin, narbomycin, and pikromycin
    notes
    Xue et al. (PMID:9770448) sequenced the Streptomyces venezuelae ATCC 15439 pik/des cluster (AF079762.1 / BGC0000898) and identified desVII and desVIII in the desosamine biosynthesis and transfer locus.
  • reference
    https://www.uniprot.org/uniprotkb/Q9ZGH7
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    Reviewed Swiss-Prot UniProtKB:Q9ZGH7 (426 aa, gene desVII) in Streptomyces venezuelae cross-references EMBL AF079762 protein AAC68677.1 and annotates obligate heterohexameric complex formation with the auxiliary protein DesVIII (UniProtKB:Q9ZGH8).
  • reference
    https://www.uniprot.org/uniprotkb/Q9ZGH8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    Reviewed Swiss-Prot UniProtKB:Q9ZGH8 (402 aa, gene desVIII) in Streptomyces venezuelae cross-references EMBL AF079762 protein AAC68676.1 and annotates the glycosyltransferase auxiliary protein required for DesVII activity.
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/AF079762.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    GenBank AF079762.1 (MIBiG BGC0000898) annotates desVIII at CDS 119..1327 (protein_id AAC68676.1) and desVII at CDS 1475..2755 (protein_id AAC68677.1).
DesVIII glycosyltransferase auxiliary protein assembles into DesVII/DesVIII glycosyltransferase complex DesVIII (UniProtKB:Q9ZGH8) is the auxiliary protein subunit required for DesVII activity in the DesVII/DesVIII complex.
DOI:10.1021/ja049967j
DOI:10.1021/bi1007657
DOI:10.1016/j.gene.2006.08.021
DOI:10.1073/pnas.95.21.12111
https://www.uniprot.org/uniprotkb/Q9ZGH7
https://www.uniprot.org/uniprotkb/Q9ZGH8
https://www.ncbi.nlm.nih.gov/nuccore/AF079762.1
  • reference
    DOI:10.1021/ja049967j
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    DesVII has already been proven responsible for the coupling of TDP-D-desosamine with both 10-deoxymethynolide and narbonolide in S. venezuelae, and it has was also shown under in vitro conditions to require an additional protein, DesVIII, for full activity
    notes
    Borisova et al. (PMID:15161264) purified Streptomyces venezuelae DesVII and DesVIII and demonstrated in vitro that DesVII requires the auxiliary protein DesVIII to transfer D-desosamine from TDP-D-desosamine onto narbonolide and 10-deoxymethynolide.
  • reference
    DOI:10.1021/bi1007657
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Together, DesVII and DesVIII serve as the glycosylation catalyst necessary to construct the bacterial macrolide antibiotics methymycin, neomethymycin, narbomycin, and pikromycin in Streptomyces venezuelae
    notes
    Borisova and Liu (PMID:20695498) characterized the tight (alpha-beta)3 heterohexameric Streptomyces venezuelae DesVII/DesVIII complex and showed that coexpression and complex formation with DesVIII are required for robust DesVII macrolide glycosyltransferase activity.
  • reference
    DOI:10.1016/j.gene.2006.08.021
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Our results demonstrated that DesVIII is needed to assist the reaction deployed by the glycosyltransferase DesVII in vivo
    notes
    Hong et al. (PMID:17049185) demonstrated by in vivo bioconversion in Streptomyces lividans that DesVIII is required alongside DesVII to glycosylate narbonolide to narbomycin and 10-deoxymethynolide to YC-17.
  • reference
    DOI:10.1073/pnas.95.21.12111
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Dedicated to the biosynthesis of dTDP-D-desosamine, an essential deoxysugar component in the macrolide antibiotics methymycin, neomethymycin, narbomycin, and pikromycin
    notes
    Xue et al. (PMID:9770448) sequenced the Streptomyces venezuelae ATCC 15439 pik/des cluster (AF079762.1 / BGC0000898) and identified desVII and desVIII in the desosamine biosynthesis and transfer locus.
  • reference
    https://www.uniprot.org/uniprotkb/Q9ZGH7
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    Reviewed Swiss-Prot UniProtKB:Q9ZGH7 (426 aa, gene desVII) in Streptomyces venezuelae cross-references EMBL AF079762 protein AAC68677.1 and annotates obligate heterohexameric complex formation with the auxiliary protein DesVIII (UniProtKB:Q9ZGH8).
  • reference
    https://www.uniprot.org/uniprotkb/Q9ZGH8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    Reviewed Swiss-Prot UniProtKB:Q9ZGH8 (402 aa, gene desVIII) in Streptomyces venezuelae cross-references EMBL AF079762 protein AAC68676.1 and annotates the glycosyltransferase auxiliary protein required for DesVII activity.
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/AF079762.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    GenBank AF079762.1 (MIBiG BGC0000898) annotates desVIII at CDS 119..1327 (protein_id AAC68676.1) and desVII at CDS 1475..2755 (protein_id AAC68677.1).
10-deoxymethynolide is glycosylated by DesVII/DesVIII glycosyltransferase complex The 12-membered macrolactone aglycone 10-deoxymethynolide (CHEBI:29461) is glycosylated at C-3 by the DesVII/DesVIII complex (RHEA:31627).
DOI:10.1021/ja049967j
DOI:10.1021/bi1007657
DOI:10.1016/j.gene.2006.08.021
DOI:10.1073/pnas.95.21.12111
https://www.uniprot.org/uniprotkb/Q9ZGH7
https://www.uniprot.org/uniprotkb/Q9ZGH8
https://www.ncbi.nlm.nih.gov/nuccore/AF079762.1
RHEA:31627
  • reference
    DOI:10.1021/ja049967j
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    DesVII has already been proven responsible for the coupling of TDP-D-desosamine with both 10-deoxymethynolide and narbonolide in S. venezuelae, and it has was also shown under in vitro conditions to require an additional protein, DesVIII, for full activity
    notes
    Borisova et al. (PMID:15161264) purified Streptomyces venezuelae DesVII and DesVIII and demonstrated in vitro that DesVII requires the auxiliary protein DesVIII to transfer D-desosamine from TDP-D-desosamine onto narbonolide and 10-deoxymethynolide.
  • reference
    DOI:10.1021/bi1007657
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Together, DesVII and DesVIII serve as the glycosylation catalyst necessary to construct the bacterial macrolide antibiotics methymycin, neomethymycin, narbomycin, and pikromycin in Streptomyces venezuelae
    notes
    Borisova and Liu (PMID:20695498) characterized the tight (alpha-beta)3 heterohexameric Streptomyces venezuelae DesVII/DesVIII complex and showed that coexpression and complex formation with DesVIII are required for robust DesVII macrolide glycosyltransferase activity.
  • reference
    DOI:10.1016/j.gene.2006.08.021
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Our results demonstrated that DesVIII is needed to assist the reaction deployed by the glycosyltransferase DesVII in vivo
    notes
    Hong et al. (PMID:17049185) demonstrated by in vivo bioconversion in Streptomyces lividans that DesVIII is required alongside DesVII to glycosylate narbonolide to narbomycin and 10-deoxymethynolide to YC-17.
  • reference
    DOI:10.1073/pnas.95.21.12111
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Dedicated to the biosynthesis of dTDP-D-desosamine, an essential deoxysugar component in the macrolide antibiotics methymycin, neomethymycin, narbomycin, and pikromycin
    notes
    Xue et al. (PMID:9770448) sequenced the Streptomyces venezuelae ATCC 15439 pik/des cluster (AF079762.1 / BGC0000898) and identified desVII and desVIII in the desosamine biosynthesis and transfer locus.
  • reference
    https://www.uniprot.org/uniprotkb/Q9ZGH7
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    Reviewed Swiss-Prot UniProtKB:Q9ZGH7 (426 aa, gene desVII) in Streptomyces venezuelae cross-references EMBL AF079762 protein AAC68677.1, EC 2.4.1.277, and RHEA:31627, annotating macrolide glycosyltransferase activity requiring DesVIII (UniProtKB:Q9ZGH8) to convert 10-deoxymethynolide and dTDP-alpha-D-desosamine to 10-deoxymethymycin (YC-17).
  • reference
    https://www.uniprot.org/uniprotkb/Q9ZGH8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    Reviewed Swiss-Prot UniProtKB:Q9ZGH8 (402 aa, gene desVIII) in Streptomyces venezuelae cross-references EMBL AF079762 protein AAC68676.1 and annotates the glycosyltransferase auxiliary protein required for DesVII activity.
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/AF079762.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    GenBank AF079762.1 (MIBiG BGC0000898) annotates desVIII at CDS 119..1327 (protein_id AAC68676.1) and desVII at CDS 1475..2755 (protein_id AAC68677.1).
  • reference
    RHEA:31627
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    RHEA:31627 grounds EC 2.4.1.277 transfer of the D-desosaminyl group from dTDP-alpha-D-desosamine(1-) (CHEBI:63260) onto 10-deoxymethynolide (CHEBI:29461) to form 10-deoxymethymycin(1+) (CHEBI:63307) and dTDP(3-); this record uses the corresponding neutral ChEBI identifiers CHEBI:27948 and CHEBI:29706.
dTDP-alpha-D-desosamine supplies the desosaminyl moiety to DesVII/DesVIII glycosyltransferase complex dTDP-alpha-D-desosamine (grounded here to neutral CHEBI:27948 rather than anionic CHEBI:63260) serves as the activated nucleotide-sugar donor for DesVII/DesVIII (RHEA:31627).
DOI:10.1021/ja049967j
DOI:10.1021/bi1007657
DOI:10.1016/j.gene.2006.08.021
DOI:10.1073/pnas.95.21.12111
https://www.uniprot.org/uniprotkb/Q9ZGH7
https://www.uniprot.org/uniprotkb/Q9ZGH8
https://www.ncbi.nlm.nih.gov/nuccore/AF079762.1
RHEA:31627
  • reference
    DOI:10.1021/ja049967j
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    DesVII has already been proven responsible for the coupling of TDP-D-desosamine with both 10-deoxymethynolide and narbonolide in S. venezuelae, and it has was also shown under in vitro conditions to require an additional protein, DesVIII, for full activity
    notes
    Borisova et al. (PMID:15161264) purified Streptomyces venezuelae DesVII and DesVIII and demonstrated in vitro that DesVII requires the auxiliary protein DesVIII to transfer D-desosamine from TDP-D-desosamine onto narbonolide and 10-deoxymethynolide.
  • reference
    DOI:10.1021/bi1007657
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Together, DesVII and DesVIII serve as the glycosylation catalyst necessary to construct the bacterial macrolide antibiotics methymycin, neomethymycin, narbomycin, and pikromycin in Streptomyces venezuelae
    notes
    Borisova and Liu (PMID:20695498) characterized the tight (alpha-beta)3 heterohexameric Streptomyces venezuelae DesVII/DesVIII complex and showed that coexpression and complex formation with DesVIII are required for robust DesVII macrolide glycosyltransferase activity.
  • reference
    DOI:10.1016/j.gene.2006.08.021
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Our results demonstrated that DesVIII is needed to assist the reaction deployed by the glycosyltransferase DesVII in vivo
    notes
    Hong et al. (PMID:17049185) demonstrated by in vivo bioconversion in Streptomyces lividans that DesVIII is required alongside DesVII to glycosylate narbonolide to narbomycin and 10-deoxymethynolide to YC-17.
  • reference
    DOI:10.1073/pnas.95.21.12111
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Dedicated to the biosynthesis of dTDP-D-desosamine, an essential deoxysugar component in the macrolide antibiotics methymycin, neomethymycin, narbomycin, and pikromycin
    notes
    Xue et al. (PMID:9770448) sequenced the Streptomyces venezuelae ATCC 15439 pik/des cluster (AF079762.1 / BGC0000898) and identified desVII and desVIII in the desosamine biosynthesis and transfer locus.
  • reference
    https://www.uniprot.org/uniprotkb/Q9ZGH7
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    Reviewed Swiss-Prot UniProtKB:Q9ZGH7 (426 aa, gene desVII) in Streptomyces venezuelae cross-references EMBL AF079762 protein AAC68677.1, EC 2.4.1.277, and RHEA:31627, annotating macrolide glycosyltransferase activity requiring DesVIII (UniProtKB:Q9ZGH8) to convert 10-deoxymethynolide and dTDP-alpha-D-desosamine to 10-deoxymethymycin (YC-17).
  • reference
    https://www.uniprot.org/uniprotkb/Q9ZGH8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    Reviewed Swiss-Prot UniProtKB:Q9ZGH8 (402 aa, gene desVIII) in Streptomyces venezuelae cross-references EMBL AF079762 protein AAC68676.1 and annotates the glycosyltransferase auxiliary protein required for DesVII activity.
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/AF079762.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    GenBank AF079762.1 (MIBiG BGC0000898) annotates desVIII at CDS 119..1327 (protein_id AAC68676.1) and desVII at CDS 1475..2755 (protein_id AAC68677.1).
  • reference
    RHEA:31627
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    RHEA:31627 grounds EC 2.4.1.277 transfer of the D-desosaminyl group from dTDP-alpha-D-desosamine(1-) (CHEBI:63260) onto 10-deoxymethynolide (CHEBI:29461) to form 10-deoxymethymycin(1+) (CHEBI:63307) and dTDP(3-); this record uses the corresponding neutral ChEBI identifiers CHEBI:27948 and CHEBI:29706.
DesVII/DesVIII glycosyltransferase complex forms 10-deoxymethymycin DesVII/DesVIII-catalyzed desosaminylation of 10-deoxymethynolide forms 10-deoxymethymycin (YC-17, grounded here to neutral CHEBI:29706 rather than cationic CHEBI:63307), the substrate of PikC.
DOI:10.1021/ja049967j
DOI:10.1021/bi1007657
DOI:10.1016/j.gene.2006.08.021
DOI:10.1073/pnas.95.21.12111
https://www.uniprot.org/uniprotkb/Q9ZGH7
https://www.uniprot.org/uniprotkb/Q9ZGH8
https://www.ncbi.nlm.nih.gov/nuccore/AF079762.1
RHEA:31627
  • reference
    DOI:10.1021/ja049967j
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    DesVII has already been proven responsible for the coupling of TDP-D-desosamine with both 10-deoxymethynolide and narbonolide in S. venezuelae, and it has was also shown under in vitro conditions to require an additional protein, DesVIII, for full activity
    notes
    Borisova et al. (PMID:15161264) purified Streptomyces venezuelae DesVII and DesVIII and demonstrated in vitro that DesVII requires the auxiliary protein DesVIII to transfer D-desosamine from TDP-D-desosamine onto narbonolide and 10-deoxymethynolide.
  • reference
    DOI:10.1021/bi1007657
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Together, DesVII and DesVIII serve as the glycosylation catalyst necessary to construct the bacterial macrolide antibiotics methymycin, neomethymycin, narbomycin, and pikromycin in Streptomyces venezuelae
    notes
    Borisova and Liu (PMID:20695498) characterized the tight (alpha-beta)3 heterohexameric Streptomyces venezuelae DesVII/DesVIII complex and showed that coexpression and complex formation with DesVIII are required for robust DesVII macrolide glycosyltransferase activity.
  • reference
    DOI:10.1016/j.gene.2006.08.021
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Our results demonstrated that DesVIII is needed to assist the reaction deployed by the glycosyltransferase DesVII in vivo
    notes
    Hong et al. (PMID:17049185) demonstrated by in vivo bioconversion in Streptomyces lividans that DesVIII is required alongside DesVII to glycosylate narbonolide to narbomycin and 10-deoxymethynolide to YC-17.
  • reference
    DOI:10.1073/pnas.95.21.12111
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Dedicated to the biosynthesis of dTDP-D-desosamine, an essential deoxysugar component in the macrolide antibiotics methymycin, neomethymycin, narbomycin, and pikromycin
    notes
    Xue et al. (PMID:9770448) sequenced the Streptomyces venezuelae ATCC 15439 pik/des cluster (AF079762.1 / BGC0000898) and identified desVII and desVIII in the desosamine biosynthesis and transfer locus.
  • reference
    https://www.uniprot.org/uniprotkb/Q9ZGH7
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    Reviewed Swiss-Prot UniProtKB:Q9ZGH7 (426 aa, gene desVII) in Streptomyces venezuelae cross-references EMBL AF079762 protein AAC68677.1, EC 2.4.1.277, and RHEA:31627, annotating macrolide glycosyltransferase activity requiring DesVIII (UniProtKB:Q9ZGH8) to convert 10-deoxymethynolide and dTDP-alpha-D-desosamine to 10-deoxymethymycin (YC-17).
  • reference
    https://www.uniprot.org/uniprotkb/Q9ZGH8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    Reviewed Swiss-Prot UniProtKB:Q9ZGH8 (402 aa, gene desVIII) in Streptomyces venezuelae cross-references EMBL AF079762 protein AAC68676.1 and annotates the glycosyltransferase auxiliary protein required for DesVII activity.
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/AF079762.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    GenBank AF079762.1 (MIBiG BGC0000898) annotates desVIII at CDS 119..1327 (protein_id AAC68676.1) and desVII at CDS 1475..2755 (protein_id AAC68677.1).
  • reference
    RHEA:31627
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-20
    notes
    RHEA:31627 grounds EC 2.4.1.277 transfer of the D-desosaminyl group from dTDP-alpha-D-desosamine(1-) (CHEBI:63260) onto 10-deoxymethynolide (CHEBI:29461) to form 10-deoxymethymycin(1+) (CHEBI:63307) and dTDP(3-); this record uses the corresponding neutral ChEBI identifiers CHEBI:27948 and CHEBI:29706.
10-deoxymethymycin is hydroxylated by PikC cytochrome P450 monooxygenase The 10-deoxymethymycin node is grounded to CHEBI:29706 and represents the YC-17 substrate named in the PikC hydroxylation paper.
DOI:10.1016/S1074-5521(98)90293-9
https://www.uniprot.org/uniprotkb/O87605
  • reference
    DOI:10.1016/S1074-5521(98)90293-9
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Purified PikC effectively converts YC-17 into methymycin and neomethymycin
    notes
    Xue et al. inactivated pikC in Streptomyces venezuelae, observed loss of hydroxylated macrolides with YC-17 and narbomycin accumulation, and showed that purified recombinant PikC converts YC-17 into methymycin and neomethymycin in vitro.
  • reference
    https://www.uniprot.org/uniprotkb/O87605
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    Reviewed UniProtKB:O87605 is the 416 aa Streptomyces venezuelae PikC/PicK cytochrome P450 monooxygenase and cross-references the AF079139 sequence submitted with the PikC characterization.
PikC cytochrome P450 monooxygenase forms methymycin Purified PikC forms both methymycin and neomethymycin from YC-17; this edge records the methymycin branch for this exact CHEBI:29630 record.
DOI:10.1016/S1074-5521(98)90293-9
https://www.uniprot.org/uniprotkb/O87605
  • reference
    DOI:10.1016/S1074-5521(98)90293-9
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Purified PikC effectively converts YC-17 into methymycin and neomethymycin
    notes
    Xue et al. inactivated pikC in Streptomyces venezuelae, observed loss of hydroxylated macrolides with YC-17 and narbomycin accumulation, and showed that purified recombinant PikC converts YC-17 into methymycin and neomethymycin in vitro.
  • reference
    https://www.uniprot.org/uniprotkb/O87605
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    Reviewed UniProtKB:O87605 is the 416 aa Streptomyces venezuelae PikC/PicK cytochrome P450 monooxygenase and cross-references the AF079139 sequence submitted with the PikC characterization.

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

Elsewhere in the fleet

Explore across X-Mech

AntibioticMech (methymycin) ↗ MediaIngredientMech (CHEBI:29630) ↗ TaxonMech: Streptomyces venezuelae (NCBITaxon:54571) ↗ PathwayMech (mibig:BGC0000094) ↗

Provenance

Source conceptSourceVersion
BGC0000094MIBIG5
CHEBI:29630CHEBI3-star

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