avilamycin C

naturalproductmech:mibig-9a5b28276d MINTED SEEDED

Grounding review: No 3-star ChEBI entry shares this structure, so the record keeps a content-hashed identifier.

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	AEIFATUAVHHRBC-GYPCSUJESA-N
SMILES	C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2[C@H](OC3(C[C@H]2O)O[C@@H]4[C@H](O[C@H](C[C@]4(O3)C)O[C@@H]5[C@H]([C@@H](O[C@@H]([C@@H]5OC)C)O[C@@H]6[C@H](O[C@H]([C@H]([C@H]6O)OC)O[C@H]7[C@@H]([C@H]8[C@H](CO7)O[C@@]9(O8)[C@H]1[C@H]([C@@]([C@H](O9)C)(C(C)O)O)OCO1)OC(=O)C(C)C)COC)O)C)C)O)OC(=O)C1=C(C(=C(C(=C1OC)Cl)O)Cl)C
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	pubchem:20055307

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 viridochromogenes Tue57 NCBITaxon:1160705	BGC_CHARACTERIZED	mibig:BGC0000026	PMID:11410376

Occurrences 0

None cited.

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000026	Streptomyces viridochromogenes Tue57 NCBITaxon:1160705	CLUSTER_DEMONSTRATED	genbank:AF333038.2

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 — biosynthesis 4 nodes, 3 edges

Streptomyces viridochromogenes Tue57 AviG2-catalyzed SAM-dependent 6-O-methylation of the D-mannose moiety contributes the shared O-methyl group in avilamycin C biosynthesis.

Subject	Predicate	Object	Notes	Evidence
6-O-demethyl avilamycin C-pathway intermediate	is 6-O-methylated by	AviG2 O-methyltransferase	MITE represents AviG2 as the O-methyltransferase that methylates the C6 hydroxyl of the D-mannose moiety in avilamycin biosynthesis. The MITE product structure canonicalizes to avilamycin A, so the analogous avilamycin C precursor remains ungrounded here.	DOI:10.1016/j.chembiol.2004.08.016 https://mite.bioinformatics.nl/repository/MITE0000001 https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk https://www.uniprot.org/uniprotkb/Q93KW1 https://www.ncbi.nlm.nih.gov/protein/AAK83184.1 reference DOI:10.1016/j.chembiol.2004.08.016 evidence type PRIMARY_EXPERIMENT snippet exact function of three methyltransferases, AviG2, AviG5, and AviG6, involved in avilamycin biosynthesis could be assigned notes Weitnauer et al. generated avilamycin methyltransferase mutants from the Streptomyces viridochromogenes Tue57 producer of avilamycins A and C and assigned AviG2 among the avilamycin O-methyltransferases. reference https://mite.bioinformatics.nl/repository/MITE0000001 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 snippet methylation of the hydroxyl group at position 6 of the D-mannose moiety notes MITE0000001 is active, lists SAM as the organic cofactor, and links AviG2 to UniProtKB:Q93KW1, GenPept AAK83184.1, MIBiG BGC0000026, and C6 O-methylation of the D-mannose moiety in avilamycin biosynthesis. reference https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MIBiG BGC0000026.5 places aviG2/AAK83184.1 inside the active Streptomyces viridochromogenes Tue57 avilamycin biosynthetic gene cluster and links the CDS to MITE0000001 at 100% identity. reference https://www.uniprot.org/uniprotkb/Q93KW1 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes Current UniProtKB:Q93KW1 resolves as a 240 aa Streptomyces viridochromogenes Tue57 aviG2 putative methyltransferase entry, cross-references EMBL AF333038 protein AAK83184.1, and carries GO:0008757 S-adenosylmethionine-dependent methyltransferase activity. reference https://www.ncbi.nlm.nih.gov/protein/AAK83184.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes NCBI Protein AAK83184.1 is the Streptomyces viridochromogenes Tue57 putative methyltransferase encoded by aviG2 at AF333038.2:28789..29511.
S-adenosyl-L-methionine	supplies a methyl group to	AviG2 O-methyltransferase	MITE lists SAM as AviG2's organic cofactor for this D-mannose 6-O-methylation reaction.	https://mite.bioinformatics.nl/repository/MITE0000001 https://www.uniprot.org/uniprotkb/Q93KW1 reference https://mite.bioinformatics.nl/repository/MITE0000001 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 snippet methylation of the hydroxyl group at position 6 of the D-mannose moiety notes MITE0000001 is active, lists SAM as the organic cofactor, and links AviG2 to UniProtKB:Q93KW1, GenPept AAK83184.1, MIBiG BGC0000026, and C6 O-methylation of the D-mannose moiety in avilamycin biosynthesis. reference https://www.uniprot.org/uniprotkb/Q93KW1 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes Current UniProtKB:Q93KW1 resolves as a 240 aa Streptomyces viridochromogenes Tue57 aviG2 putative methyltransferase entry, cross-references EMBL AF333038 protein AAK83184.1, and carries GO:0008757 S-adenosylmethionine-dependent methyltransferase activity.
AviG2 O-methyltransferase	contributes C6 D-mannose O-methylation to	avilamycin C	Avilamycin C is the second BGC0000026 compound in the committed MIBiG source inventory; this edge records the shared D-mannose C6 O-methylation rather than asserting that MITE's avilamycin A product is the exact avilamycin C final structure.	DOI:10.1016/j.chembiol.2004.08.016 https://mite.bioinformatics.nl/repository/MITE0000001 https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk https://www.uniprot.org/uniprotkb/Q93KW1 https://www.ncbi.nlm.nih.gov/protein/AAK83184.1 reference DOI:10.1016/j.chembiol.2004.08.016 evidence type PRIMARY_EXPERIMENT snippet exact function of three methyltransferases, AviG2, AviG5, and AviG6, involved in avilamycin biosynthesis could be assigned notes Weitnauer et al. generated avilamycin methyltransferase mutants from the Streptomyces viridochromogenes Tue57 producer of avilamycins A and C and assigned AviG2 among the avilamycin O-methyltransferases. reference https://mite.bioinformatics.nl/repository/MITE0000001 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 snippet methylation of the hydroxyl group at position 6 of the D-mannose moiety notes MITE0000001 is active, lists SAM as the organic cofactor, and links AviG2 to UniProtKB:Q93KW1, GenPept AAK83184.1, MIBiG BGC0000026, and C6 O-methylation of the D-mannose moiety in avilamycin biosynthesis. reference https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MIBiG BGC0000026.5 places aviG2/AAK83184.1 inside the active Streptomyces viridochromogenes Tue57 avilamycin biosynthetic gene cluster and links the CDS to MITE0000001 at 100% identity. reference https://www.uniprot.org/uniprotkb/Q93KW1 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes Current UniProtKB:Q93KW1 resolves as a 240 aa Streptomyces viridochromogenes Tue57 aviG2 putative methyltransferase entry, cross-references EMBL AF333038 protein AAK83184.1, and carries GO:0008757 S-adenosylmethionine-dependent methyltransferase activity. reference https://www.ncbi.nlm.nih.gov/protein/AAK83184.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes NCBI Protein AAK83184.1 is the Streptomyces viridochromogenes Tue57 putative methyltransferase encoded by aviG2 at AF333038.2:28789..29511.

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

Causal graph — biosynthesis 4 nodes, 3 edges

Streptomyces viridochromogenes Tue57 AviG6-catalyzed SAM-dependent 2-O-methylation of the D-mannose moiety contributes the shared O-methyl group in avilamycin C biosynthesis.

Subject	Predicate	Object	Notes	Evidence
2-O-demethyl avilamycin C-pathway intermediate	is 2-O-methylated by	AviG6 O-methyltransferase	MITE represents AviG6 as the O-methyltransferase that methylates the C2 hydroxyl of the D-mannose moiety in avilamycin biosynthesis. The MITE product structure canonicalizes to avilamycin A, so the analogous avilamycin C precursor remains ungrounded here.	DOI:10.1016/j.chembiol.2004.08.016 https://mite.bioinformatics.nl/repository/MITE0000003 https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk https://www.uniprot.org/uniprotkb/Q93KV9 https://www.ncbi.nlm.nih.gov/protein/AAK83186.1 reference DOI:10.1016/j.chembiol.2004.08.016 evidence type PRIMARY_EXPERIMENT snippet exact function of three methyltransferases, AviG2, AviG5, and AviG6, involved in avilamycin biosynthesis could be assigned notes Weitnauer et al. generated avilamycin methyltransferase mutants from the Streptomyces viridochromogenes Tue57 producer of avilamycins A and C and assigned AviG6 among the avilamycin O-methyltransferases. reference https://mite.bioinformatics.nl/repository/MITE0000003 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 snippet methylation of the hydroxyl group at position 2 of the D-mannose moiety notes MITE0000003 is active, lists SAM as the organic cofactor, and links AviG6 to UniProtKB:Q93KV9, GenPept AAK83186.1, MIBiG BGC0000026, and C2 O-methylation of the D-mannose moiety in avilamycin biosynthesis. reference https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MIBiG BGC0000026.5 places aviG6/AAK83186.1 inside the active Streptomyces viridochromogenes Tue57 avilamycin biosynthetic gene cluster and links the CDS to MITE0000003 at 100% identity. reference https://www.uniprot.org/uniprotkb/Q93KV9 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes Current UniProtKB:Q93KV9 resolves as a 239 aa Streptomyces viridochromogenes Tue57 aviG6 putative methyltransferase entry, cross-references EMBL AF333038 protein AAK83186.1, and carries GO:0008171 O-methyltransferase activity. reference https://www.ncbi.nlm.nih.gov/protein/AAK83186.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes NCBI Protein AAK83186.1 is the Streptomyces viridochromogenes Tue57 putative methyltransferase encoded by aviG6 at AF333038.2:30514..31233.
S-adenosyl-L-methionine	supplies a methyl group to	AviG6 O-methyltransferase	MITE lists SAM as AviG6's organic cofactor for this D-mannose 2-O-methylation reaction.	https://mite.bioinformatics.nl/repository/MITE0000003 https://www.uniprot.org/uniprotkb/Q93KV9 reference https://mite.bioinformatics.nl/repository/MITE0000003 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 snippet methylation of the hydroxyl group at position 2 of the D-mannose moiety notes MITE0000003 is active, lists SAM as the organic cofactor, and links AviG6 to UniProtKB:Q93KV9, GenPept AAK83186.1, MIBiG BGC0000026, and C2 O-methylation of the D-mannose moiety in avilamycin biosynthesis. reference https://www.uniprot.org/uniprotkb/Q93KV9 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes Current UniProtKB:Q93KV9 resolves as a 239 aa Streptomyces viridochromogenes Tue57 aviG6 putative methyltransferase entry, cross-references EMBL AF333038 protein AAK83186.1, and carries GO:0008171 O-methyltransferase activity.
AviG6 O-methyltransferase	contributes C2 D-mannose O-methylation to	avilamycin C	Avilamycin C is the second BGC0000026 compound in the committed MIBiG source inventory; this edge records the shared D-mannose C2 O-methylation rather than asserting that MITE's avilamycin A product is the exact avilamycin C final structure.	DOI:10.1016/j.chembiol.2004.08.016 https://mite.bioinformatics.nl/repository/MITE0000003 https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk https://www.uniprot.org/uniprotkb/Q93KV9 https://www.ncbi.nlm.nih.gov/protein/AAK83186.1 reference DOI:10.1016/j.chembiol.2004.08.016 evidence type PRIMARY_EXPERIMENT snippet exact function of three methyltransferases, AviG2, AviG5, and AviG6, involved in avilamycin biosynthesis could be assigned notes Weitnauer et al. generated avilamycin methyltransferase mutants from the Streptomyces viridochromogenes Tue57 producer of avilamycins A and C and assigned AviG6 among the avilamycin O-methyltransferases. reference https://mite.bioinformatics.nl/repository/MITE0000003 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 snippet methylation of the hydroxyl group at position 2 of the D-mannose moiety notes MITE0000003 is active, lists SAM as the organic cofactor, and links AviG6 to UniProtKB:Q93KV9, GenPept AAK83186.1, MIBiG BGC0000026, and C2 O-methylation of the D-mannose moiety in avilamycin biosynthesis. reference https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MIBiG BGC0000026.5 places aviG6/AAK83186.1 inside the active Streptomyces viridochromogenes Tue57 avilamycin biosynthetic gene cluster and links the CDS to MITE0000003 at 100% identity. reference https://www.uniprot.org/uniprotkb/Q93KV9 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes Current UniProtKB:Q93KV9 resolves as a 239 aa Streptomyces viridochromogenes Tue57 aviG6 putative methyltransferase entry, cross-references EMBL AF333038 protein AAK83186.1, and carries GO:0008171 O-methyltransferase activity. reference https://www.ncbi.nlm.nih.gov/protein/AAK83186.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes NCBI Protein AAK83186.1 is the Streptomyces viridochromogenes Tue57 putative methyltransferase encoded by aviG6 at AF333038.2:30514..31233.

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

Causal graph — biosynthesis 4 nodes, 3 edges

Streptomyces viridochromogenes Tue57 AviG5-catalyzed SAM-dependent 4-O-methylation of the D-fucose moiety contributes the shared O-methyl group in avilamycin C biosynthesis.

Subject	Predicate	Object	Notes	Evidence
4-O-demethyl avilamycin C-pathway intermediate	is 4-O-methylated by	AviG5 O-methyltransferase	MITE represents AviG5 as the O-methyltransferase that methylates the C4 hydroxyl of the D-fucose moiety in avilamycin biosynthesis. The MITE product structure canonicalizes to avilamycin A, so the analogous avilamycin C precursor remains ungrounded here.	DOI:10.1016/j.chembiol.2004.08.016 https://mite.bioinformatics.nl/repository/MITE0000004 https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk https://www.uniprot.org/uniprotkb/Q93KW5 https://www.ncbi.nlm.nih.gov/protein/AAK83180.1 reference DOI:10.1016/j.chembiol.2004.08.016 evidence type PRIMARY_EXPERIMENT snippet exact function of three methyltransferases, AviG2, AviG5, and AviG6, involved in avilamycin biosynthesis could be assigned notes Weitnauer et al. generated avilamycin methyltransferase mutants from the Streptomyces viridochromogenes Tue57 producer of avilamycins A and C and assigned AviG5 among the avilamycin O-methyltransferases. reference https://mite.bioinformatics.nl/repository/MITE0000004 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 snippet methylation of the hydroxyl group at position 4 of the D-fucose moiety notes MITE0000004 is active, lists SAM as the organic cofactor, and links AviG5 to UniProtKB:Q93KW5, GenPept AAK83180.1, MIBiG BGC0000026, and C4 O-methylation of the D-fucose moiety in avilamycin biosynthesis. reference https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MIBiG BGC0000026.5 places aviG5/AAK83180.1 inside the active Streptomyces viridochromogenes Tue57 avilamycin biosynthetic gene cluster and links the CDS to MITE0000004 at 100% identity. reference https://www.uniprot.org/uniprotkb/Q93KW5 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes Current UniProtKB:Q93KW5 resolves as a 199 aa Streptomyces viridochromogenes Tue57 aviG5 putative methyltransferase entry, cross-references EMBL AF333038 protein AAK83180.1, and carries SAM-dependent methyltransferase family/domain cross-references. reference https://www.ncbi.nlm.nih.gov/protein/AAK83180.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes NCBI Protein AAK83180.1 is the Streptomyces viridochromogenes Tue57 putative methyltransferase encoded by aviG5 at AF333038.2:25011..25610.
S-adenosyl-L-methionine	supplies a methyl group to	AviG5 O-methyltransferase	MITE lists SAM as AviG5's organic cofactor for this D-fucose 4-O-methylation reaction.	https://mite.bioinformatics.nl/repository/MITE0000004 https://www.uniprot.org/uniprotkb/Q93KW5 reference https://mite.bioinformatics.nl/repository/MITE0000004 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 snippet methylation of the hydroxyl group at position 4 of the D-fucose moiety notes MITE0000004 is active, lists SAM as the organic cofactor, and links AviG5 to UniProtKB:Q93KW5, GenPept AAK83180.1, MIBiG BGC0000026, and C4 O-methylation of the D-fucose moiety in avilamycin biosynthesis. reference https://www.uniprot.org/uniprotkb/Q93KW5 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes Current UniProtKB:Q93KW5 resolves as a 199 aa Streptomyces viridochromogenes Tue57 aviG5 putative methyltransferase entry, cross-references EMBL AF333038 protein AAK83180.1, and carries SAM-dependent methyltransferase family/domain cross-references.
AviG5 O-methyltransferase	contributes C4 D-fucose O-methylation to	avilamycin C	Avilamycin C is the second BGC0000026 compound in the committed MIBiG source inventory; this edge records the shared D-fucose C4 O-methylation rather than asserting that MITE's avilamycin A product is the exact avilamycin C final structure.	DOI:10.1016/j.chembiol.2004.08.016 https://mite.bioinformatics.nl/repository/MITE0000004 https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk https://www.uniprot.org/uniprotkb/Q93KW5 https://www.ncbi.nlm.nih.gov/protein/AAK83180.1 reference DOI:10.1016/j.chembiol.2004.08.016 evidence type PRIMARY_EXPERIMENT snippet exact function of three methyltransferases, AviG2, AviG5, and AviG6, involved in avilamycin biosynthesis could be assigned notes Weitnauer et al. generated avilamycin methyltransferase mutants from the Streptomyces viridochromogenes Tue57 producer of avilamycins A and C and assigned AviG5 among the avilamycin O-methyltransferases. reference https://mite.bioinformatics.nl/repository/MITE0000004 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 snippet methylation of the hydroxyl group at position 4 of the D-fucose moiety notes MITE0000004 is active, lists SAM as the organic cofactor, and links AviG5 to UniProtKB:Q93KW5, GenPept AAK83180.1, MIBiG BGC0000026, and C4 O-methylation of the D-fucose moiety in avilamycin biosynthesis. reference https://mibig.secondarymetabolites.org/repository/BGC0000026.5/BGC0000026.gbk evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MIBiG BGC0000026.5 places aviG5/AAK83180.1 inside the active Streptomyces viridochromogenes Tue57 avilamycin biosynthetic gene cluster and links the CDS to MITE0000004 at 100% identity. reference https://www.uniprot.org/uniprotkb/Q93KW5 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes Current UniProtKB:Q93KW5 resolves as a 199 aa Streptomyces viridochromogenes Tue57 aviG5 putative methyltransferase entry, cross-references EMBL AF333038 protein AAK83180.1, and carries SAM-dependent methyltransferase family/domain cross-references. reference https://www.ncbi.nlm.nih.gov/protein/AAK83180.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes NCBI Protein AAK83180.1 is the Streptomyces viridochromogenes Tue57 putative methyltransferase encoded by aviG5 at AF333038.2:25011..25610.

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

Explore across X-Mech

AntibioticMech (avilamycin C) ↗ MediaIngredientMech (naturalproductmech:mibig-9a5b28276d) ↗ TaxonMech: Streptomyces viridochromogenes Tue57 (NCBITaxon:1160705) ↗ PathwayMech (mibig:BGC0000026) ↗

Provenance

Source concept	Source	Version
BGC0000026	MIBIG	5

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