pikromycin

CHEBI:29665 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 macrolide antibiotic that is biosynthesised by Streptomyces venezuelae.

Structure

Standard InChIKey	UZQBOFAUUTZOQE-VSLWXVDYSA-N
SMILES	CC[C@@H]1[C@@](/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O[C@H]2[C@@H]([C@H](C[C@H](O2)C)N(C)C)O)C)C)(C)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 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 venezuelae Strain: ATCC 15439 NCBITaxon:54571	SOURCE_ASSERTION	mibig:BGC0000898	PMID:9770448, DOI:10.1073/pnas.95.21.12111 reference PMID:9770448 evidence type DATABASE_ASSERTION notes MIBiG BGC0000898 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 AF079762.1 explicitly identify Streptomyces venezuelae ATCC 15439 as the sequenced pikromycin/desosamine producer strain for BGC0000898:2. Preserve NCBITaxon:54571 and existing SOURCE_ASSERTION/CLUSTER_UNSTATED grades; deposit-partition boundary with BGC0000094 remains tracked in #1012. See issue #1010. Taxon identity and evidence grade are unchanged; this is not a species-wide experiment. MIBiG source row BGC0000898:2; SHA256 224e597f0ea6fd4934bbbe480086fca606e478396c63e45cc1792ae879613923. Curator: antigravity; date: 2026-10-22.

Occurrences 2

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 albus NCBITaxon:1888	LOTUS	DOI:10.1021/NP060026P
Streptomyces venezuelae NCBITaxon:54571	CHEBI	PMID:16724858

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000898	Streptomyces venezuelae NCBITaxon:54571	CLUSTER_UNSTATED	genbank:AF079762.1

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
1	DesVII macrolide glycosyltransferase UniProtKB:Q9ZGH7		CHEBI:29650 → CHEBI:29649	DOI:10.1021/ja049967j
2	PikC cytochrome P450 monooxygenase UniProtKB:O87605	RHEA:39887	CHEBI:29649 → CHEBI:29665	DOI:10.1016/S1074-5521(98)90293-9

Step 1: DesVII (UniProtKB:Q9ZGH7, AAC68677.1, AF079762.1:1475..2755, EC 2.4.1.277 / EC 2.4.1.278) 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 14-membered macrolactone aglycone narbonolide (CHEBI:29650) to form narbomycin (CHEBI:29649), the immediate substrate of PikC.

Step 2: PikC hydroxylates the 14-membered macrolide narbomycin to form pikromycin. RHEA:39887 grounds the same monooxygenase reaction using the corresponding protonated ChEBI species.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 8 nodes, 7 edges

Partial Streptomyces venezuelae pikromycin biosynthesis graph for DesVII/DesVIII-catalyzed narbonolide glycosylation to narbomycin followed by PikC-catalyzed hydroxylation to pikromycin.

Subject	Predicate	Object	Notes	Evidence
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).
narbonolide	is glycosylated by	DesVII/DesVIII glycosyltransferase complex	The 14-membered macrolactone aglycone narbonolide (CHEBI:29650) is glycosylated at C-5 by 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 macrolide glycosyltransferase activity requiring DesVIII (UniProtKB:Q9ZGH8) to convert narbonolide and dTDP-alpha-D-desosamine to narbomycin. 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).
dTDP-alpha-D-desosamine	supplies the desosaminyl moiety to	DesVII/DesVIII glycosyltransferase complex	dTDP-alpha-D-desosamine (grounded here to neutral CHEBI:27948) serves as the activated nucleotide-sugar donor for DesVII/DesVIII.	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 macrolide glycosyltransferase activity requiring DesVIII (UniProtKB:Q9ZGH8) to convert narbonolide and dTDP-alpha-D-desosamine to narbomycin. 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).
DesVII/DesVIII glycosyltransferase complex	forms	narbomycin	DesVII/DesVIII-catalyzed desosaminylation of narbonolide forms narbomycin (CHEBI:29649), 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 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 macrolide glycosyltransferase activity requiring DesVIII (UniProtKB:Q9ZGH8) to convert narbonolide and dTDP-alpha-D-desosamine to narbomycin. 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).
narbomycin	is hydroxylated by	PikC cytochrome P450 monooxygenase	The narbomycin node is grounded to the neutral CHEBI:29649 record rather than the protonated CHEBI:76801 species used in RHEA:39887.	DOI:10.1016/S1074-5521(98)90293-9 https://www.uniprot.org/uniprotkb/O87605 RHEA:39887 reference DOI:10.1016/S1074-5521(98)90293-9 evidence type PRIMARY_EXPERIMENT snippet Purified PikC effectively converts YC-17 into methymycin and neomethymycin and narbomycin into pikromycin in vitro 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 narbomycin into pikromycin in vitro. reference https://www.uniprot.org/uniprotkb/O87605 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes Reviewed UniProtKB:O87605 is the 416 aa Streptomyces venezuelae PikC/PicK cytochrome P450 monooxygenase, has gene name pikC, annotates EC 1.14.15.33, and cross-references the RHEA:39887 narbomycin-to-pikromycin reaction. reference RHEA:39887 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes RHEA:39887 grounds PikC-catalyzed hydroxylation of narbomycin(1+) to pikromycin(1+) through EC 1.14.15.33; this record uses neutral CHEBI:29649 and CHEBI:29665 for the corresponding NaturalProductMech structures.
PikC cytochrome P450 monooxygenase	forms	pikromycin	Purified PikC forms pikromycin from narbomycin; this edge records the pikromycin branch for this exact CHEBI:29665 record.	DOI:10.1016/S1074-5521(98)90293-9 https://www.uniprot.org/uniprotkb/O87605 RHEA:39887 reference DOI:10.1016/S1074-5521(98)90293-9 evidence type PRIMARY_EXPERIMENT snippet Purified PikC effectively converts YC-17 into methymycin and neomethymycin and narbomycin into pikromycin in vitro 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 narbomycin into pikromycin in vitro. reference https://www.uniprot.org/uniprotkb/O87605 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes Reviewed UniProtKB:O87605 is the 416 aa Streptomyces venezuelae PikC/PicK cytochrome P450 monooxygenase, has gene name pikC, annotates EC 1.14.15.33, and cross-references the RHEA:39887 narbomycin-to-pikromycin reaction. reference RHEA:39887 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes RHEA:39887 grounds PikC-catalyzed hydroxylation of narbomycin(1+) to pikromycin(1+) through EC 1.14.15.33; this record uses neutral CHEBI:29649 and CHEBI:29665 for the corresponding NaturalProductMech structures.

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

Elsewhere in the fleet

AntibioticMech — CHEBI:29665 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (pikromycin) ↗ MediaIngredientMech (CHEBI:29665) ↗ TaxonMech: Streptomyces venezuelae (NCBITaxon:54571) ↗ PathwayMech (mibig:BGC0000898) ↗

Provenance

Source concept	Source	Version
BGC0000898	MIBIG	5
CHEBI:29665	CHEBI	3-star

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