cyclooctatin

naturalproductmech:mibig-3835812e03 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	MSKFOQCDNOFJAT-SOFYXZRVSA-N
SMILES	CC(C)C\1CCC2(/C1=C\CC(C3C(CC(C3C2)CO)O)(C)O)C
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	pubchem:5467942

Filing pathway

Terpenoids — 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 terpene, 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 melanosporofaciens NCBITaxon:67327	BGC_CHARACTERIZED	mibig:BGC0000677	PMID:19635410

Occurrences 5

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:10.1007/S00253-013-5440-6
Streptomyces albus NCBITaxon:1888	LOTUS	DOI:10.1016/S1875-5364(17)30018-3
Streptomyces albus NCBITaxon:1888	LOTUS	DOI:10.1021/ACS.JNATPROD.6B00676
Streptomyces albus NCBITaxon:1888	LOTUS	DOI:10.1186/1471-2164-15-97
Streptomyces albus NCBITaxon:1888	LOTUS	DOI:10.7164/ANTIBIOTICS.45.1587

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000677	Streptomyces melanosporofaciens NCBITaxon:67327	CLUSTER_DEMONSTRATED	genbank:AB448947.1

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	CotB2 UniProtKB:C9K1X5	RHEA:41628	CHEBI:57533 → CHEBI:78352	DOI:10.1016/j.chembiol.2009.06.007
2	CotB3 cyclooctat-9-en-7-ol 5-monooxygenase UniProtKB:C9K1X6	RHEA:56820	CHEBI:78352 → CHEBI:141020	DOI:10.1016/j.chembiol.2009.06.007
3	CotB4 cyclooctatin synthase UniProtKB:C9K1X7	RHEA:56824	CHEBI:141020 → CHEBI:78370	DOI:10.1016/j.chembiol.2009.06.007

Step 1: CotB2 cyclizes geranylgeranyl diphosphate to cyclooctat-9-en-7-ol, the first committed diterpene cyclization in cyclooctatin biosynthesis.

Step 2: CotB3 performs the first P450 hydroxylation downstream of CotB2, converting cyclooctat-9-en-7-ol to cyclooctat-9-en-5,7-diol.

Step 3: CotB4 performs the terminal C-18 P450 hydroxylation from cyclooctat-9-en-5,7-diol to cyclooctatin. CHEBI:78370 is the stereocomplete Rhea product; the NaturalProductRecord remains grounded to the partial-stereo MIBiG structure pending a record-level stereochemistry review.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 7 nodes, 6 edges

Streptomyces melanosporofaciens cyclooctatin biosynthesis graph for CotB2 cyclization of geranylgeranyl diphosphate and CotB3/CotB4 P450 hydroxylations to cyclooctatin.

Subject	Predicate	Object	Evidence
geranylgeranyl diphosphate(3-)	is cyclized by	CotB2	DOI:10.1016/j.chembiol.2009.06.007 https://www.uniprot.org/uniprotkb/C9K1X5 https://www.ncbi.nlm.nih.gov/protein/BAI44338.1 reference DOI:10.1016/j.chembiol.2009.06.007 evidence type PRIMARY_EXPERIMENT snippet Incubation of the recombinant CotB2 with GGDP resulted in the formation of cyclooctat-9-en-7-ol notes Kim et al. cloned the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus and assigned CotB2 to the GGDP to cyclooctat-9-en-7-ol cyclization in vitro. reference https://www.uniprot.org/uniprotkb/C9K1X5 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:C9K1X5 is the reviewed Streptomyces melanosporofaciens CotB2 entry, maps to EMBL AB448947 protein BAI44338.1, and annotates RHEA:41628. reference https://www.ncbi.nlm.nih.gov/protein/BAI44338.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept BAI44338.1 is the AB448947.1 geranylgeranyl diphosphate cyclase coding sequence from the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus.
CotB2	forms	cyclooctat-9-en-7-ol	DOI:10.1016/j.chembiol.2009.06.007 https://www.uniprot.org/uniprotkb/C9K1X5 https://www.ncbi.nlm.nih.gov/protein/BAI44338.1 reference DOI:10.1016/j.chembiol.2009.06.007 evidence type PRIMARY_EXPERIMENT snippet Incubation of the recombinant CotB2 with GGDP resulted in the formation of cyclooctat-9-en-7-ol notes Kim et al. cloned the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus and assigned CotB2 to the GGDP to cyclooctat-9-en-7-ol cyclization in vitro. reference https://www.uniprot.org/uniprotkb/C9K1X5 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:C9K1X5 is the reviewed Streptomyces melanosporofaciens CotB2 entry, maps to EMBL AB448947 protein BAI44338.1, and annotates RHEA:41628. reference https://www.ncbi.nlm.nih.gov/protein/BAI44338.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept BAI44338.1 is the AB448947.1 geranylgeranyl diphosphate cyclase coding sequence from the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus.
cyclooctat-9-en-7-ol	is hydroxylated by	CotB3	DOI:10.1016/j.chembiol.2009.06.007 DOI:10.1186/s12934-016-0487-6 https://www.uniprot.org/uniprotkb/C9K1X6 https://www.ncbi.nlm.nih.gov/protein/BAI44339.1 reference DOI:10.1016/j.chembiol.2009.06.007 evidence type PRIMARY_EXPERIMENT snippet complete cyclooctatin biosynthetic gene cluster consists of four genes, cotB1 to cotB4 notes Kim et al. cloned the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus, heterologously produced cyclooctatin in Streptomyces albus, and assigned the minimal cotB1-cotB4 cluster to GGDP synthesis, CotB2 cyclization, and two cytochrome P450 hydroxylations. reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT snippet 100 μM of cyclooctat-9-en-7-ol (CotB3) or cyclooct-9-en-5,7-diol (CotB4) notes Gorner et al. reconstituted CotB3 and CotB4 activity with heterologous redox partners in Escherichia coli and measured conversion of cyclooctat-9-en-7-ol by CotB3 and cyclooctat-9-en-5,7-diol by CotB4. reference https://www.uniprot.org/uniprotkb/C9K1X6 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes UniProtKB:C9K1X6 is the reviewed Streptomyces melanosporofaciens CotB3 entry, maps to EMBL AB448947 protein BAI44339.1, and annotates RHEA:56820 for cyclooctat-9-en-7-ol 5-monooxygenase activity. reference https://www.ncbi.nlm.nih.gov/protein/BAI44339.1 evidence type DATABASE_ASSERTION snippet product="P450" retrieved on 2026-09-28 notes NCBI GenPept BAI44339.1 is the AB448947.1 CotB3 P450 coding sequence from the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus.
CotB3	forms	cyclooctat-9-en-5,7-diol	DOI:10.1016/j.chembiol.2009.06.007 DOI:10.1186/s12934-016-0487-6 https://www.uniprot.org/uniprotkb/C9K1X6 https://www.ncbi.nlm.nih.gov/protein/BAI44339.1 reference DOI:10.1016/j.chembiol.2009.06.007 evidence type PRIMARY_EXPERIMENT snippet complete cyclooctatin biosynthetic gene cluster consists of four genes, cotB1 to cotB4 notes Kim et al. cloned the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus, heterologously produced cyclooctatin in Streptomyces albus, and assigned the minimal cotB1-cotB4 cluster to GGDP synthesis, CotB2 cyclization, and two cytochrome P450 hydroxylations. reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT snippet 100 μM of cyclooctat-9-en-7-ol (CotB3) or cyclooct-9-en-5,7-diol (CotB4) notes Gorner et al. reconstituted CotB3 and CotB4 activity with heterologous redox partners in Escherichia coli and measured conversion of cyclooctat-9-en-7-ol by CotB3 and cyclooctat-9-en-5,7-diol by CotB4. reference https://www.uniprot.org/uniprotkb/C9K1X6 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes UniProtKB:C9K1X6 is the reviewed Streptomyces melanosporofaciens CotB3 entry, maps to EMBL AB448947 protein BAI44339.1, and annotates RHEA:56820 for cyclooctat-9-en-7-ol 5-monooxygenase activity. reference https://www.ncbi.nlm.nih.gov/protein/BAI44339.1 evidence type DATABASE_ASSERTION snippet product="P450" retrieved on 2026-09-28 notes NCBI GenPept BAI44339.1 is the AB448947.1 CotB3 P450 coding sequence from the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus.
cyclooctat-9-en-5,7-diol	is hydroxylated by	CotB4	DOI:10.1016/j.chembiol.2009.06.007 DOI:10.1186/s12934-016-0487-6 https://www.uniprot.org/uniprotkb/C9K1X7 https://www.ncbi.nlm.nih.gov/protein/BAI44340.1 reference DOI:10.1016/j.chembiol.2009.06.007 evidence type PRIMARY_EXPERIMENT snippet complete cyclooctatin biosynthetic gene cluster consists of four genes, cotB1 to cotB4 notes Kim et al. cloned the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus, heterologously produced cyclooctatin in Streptomyces albus, and assigned the minimal cotB1-cotB4 cluster to GGDP synthesis, CotB2 cyclization, and two cytochrome P450 hydroxylations. reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT snippet 100 μM of cyclooctat-9-en-7-ol (CotB3) or cyclooct-9-en-5,7-diol (CotB4) notes Gorner et al. reconstituted CotB3 and CotB4 activity with heterologous redox partners in Escherichia coli and measured conversion of cyclooctat-9-en-7-ol by CotB3 and cyclooctat-9-en-5,7-diol by CotB4. reference https://www.uniprot.org/uniprotkb/C9K1X7 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes UniProtKB:C9K1X7 is the reviewed Streptomyces melanosporofaciens CotB4 entry, maps to EMBL AB448947 protein BAI44340.1, and annotates RHEA:56824 for cyclooctatin synthase activity. reference https://www.ncbi.nlm.nih.gov/protein/BAI44340.1 evidence type DATABASE_ASSERTION snippet product="P450" retrieved on 2026-09-28 notes NCBI GenPept BAI44340.1 is the AB448947.1 CotB4 P450 coding sequence from the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus.
CotB4	forms	cyclooctatin	DOI:10.1016/j.chembiol.2009.06.007 DOI:10.1186/s12934-016-0487-6 https://www.uniprot.org/uniprotkb/C9K1X7 https://www.ncbi.nlm.nih.gov/protein/BAI44340.1 reference DOI:10.1016/j.chembiol.2009.06.007 evidence type PRIMARY_EXPERIMENT snippet complete cyclooctatin biosynthetic gene cluster consists of four genes, cotB1 to cotB4 notes Kim et al. cloned the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus, heterologously produced cyclooctatin in Streptomyces albus, and assigned the minimal cotB1-cotB4 cluster to GGDP synthesis, CotB2 cyclization, and two cytochrome P450 hydroxylations. reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT snippet 100 μM of cyclooctat-9-en-7-ol (CotB3) or cyclooct-9-en-5,7-diol (CotB4) notes Gorner et al. reconstituted CotB3 and CotB4 activity with heterologous redox partners in Escherichia coli and measured conversion of cyclooctat-9-en-7-ol by CotB3 and cyclooctat-9-en-5,7-diol by CotB4. reference https://www.uniprot.org/uniprotkb/C9K1X7 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes UniProtKB:C9K1X7 is the reviewed Streptomyces melanosporofaciens CotB4 entry, maps to EMBL AB448947 protein BAI44340.1, and annotates RHEA:56824 for cyclooctatin synthase activity. reference https://www.ncbi.nlm.nih.gov/protein/BAI44340.1 evidence type DATABASE_ASSERTION snippet product="P450" retrieved on 2026-09-28 notes NCBI GenPept BAI44340.1 is the AB448947.1 CotB4 P450 coding sequence from the Streptomyces melanosporofaciens MI614-43F2 cyclooctatin locus.

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

Causal graph — biosynthesis 4 nodes, 3 edges

Non-native AfR/Afx redox-pair support of CotB3/CotB4 in engineered Escherichia coli BL21(DE3). UniProt nodes identify references for the qualified synthetic constructs. Whole-cell evidence does not establish purified electron transfer, a physical complex or native partners. No new native-producer claim or stereochemical assignment is made.

Subject	Predicate	Object	Notes	Evidence
AfR (+Gly construct; reference accession)	with coexpressed Afx supports	CotB3/CotB4 hydroxylation in engineered E. coli	Paired-system evidence; individual sufficiency is not established.	DOI:10.1186/s12934-016-0487-6 https://www.uniprot.org/uniprotkb/S4M5B3 https://www.ncbi.nlm.nih.gov/protein/WP_020277402.1 https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT notes Results and Methods: the coexpressed redox pair supported CotB3/CotB4 in whole-cell assays. retrieved on 2026-10-09 snippet whole cell catalysis experiments were carried out reference https://www.uniprot.org/uniprotkb/S4M5B3 evidence type DATABASE_ASSERTION notes Unreviewed reference, entry version 40, sequence version 1; 416 aa, STAFG_8584, Streptomyces afghaniensis 772, taxon 1283301. Sequence equals GenPept EPJ34383.1 and the paper-cited RefSeq WP_020277402.1; the accession identifies the reference, not an identical synthetic construct. retrieved on 2026-10-09 reference https://www.ncbi.nlm.nih.gov/protein/WP_020277402.1 evidence type DATABASE_ASSERTION notes Paper-cited reference sequence matches EPJ34383.1 and its independently translated strain-772 genomic CDS. retrieved on 2026-10-09 reference https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf evidence type CURATOR_INFERENCE notes Literal Figure S19 ORF translation is 417 aa: Gly inserted after initiator Met relative to the 416-aa reference. This is a sequence comparison, not a claim that the assayed construct equals the canonical sequence. retrieved on 2026-10-09
Afx (MTN-deleted construct; reference accession)	with coexpressed AfR supports	CotB3/CotB4 hydroxylation in engineered E. coli	Paired-system evidence; individual sufficiency is not established.	DOI:10.1186/s12934-016-0487-6 https://www.uniprot.org/uniprotkb/S4MH50 https://www.ncbi.nlm.nih.gov/protein/WP_020276845.1 https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT notes Results and Methods: the coexpressed redox pair supported CotB3/CotB4 in whole-cell assays. retrieved on 2026-10-09 reference https://www.uniprot.org/uniprotkb/S4MH50 evidence type DATABASE_ASSERTION notes Unreviewed reference, entry version 42, sequence version 1; 110 aa, STAFG_8018, Streptomyces afghaniensis 772, taxon 1283301. Sequence equals GenPept EPJ34910.1 and the paper-cited RefSeq WP_020276845.1; the accession identifies the reference, not an identical synthetic construct. retrieved on 2026-10-09 reference https://www.ncbi.nlm.nih.gov/protein/WP_020276845.1 evidence type DATABASE_ASSERTION notes Paper-cited reference sequence matches EPJ34910.1 and its independently translated strain-772 genomic CDS. retrieved on 2026-10-09 reference https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf evidence type CURATOR_INFERENCE notes Literal Figure S19 ORF translation is 107 aa: the reference N-terminal MTN is absent. This is a sequence comparison, not a claim that the assayed construct equals the 110-aa canonical sequence. retrieved on 2026-10-09
CotB3/CotB4 hydroxylation in engineered E. coli	yields	cyclooctatin (reported product)	The reported product is not asserted identical to the partial-stereo owner or assigned an exact stereochemical identifier in this graph.	DOI:10.1186/s12934-016-0487-6 https://www.ebi.ac.uk/chebi/CHEBI:78370 reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT notes Results, Figure 1 and Additional file 1 report cyclooctatin formation and spectroscopic characterization in the engineered production system. retrieved on 2026-10-09 reference https://www.ebi.ac.uk/chebi/CHEBI:78370 evidence type CURATOR_INFERENCE notes ChEBI cyclooctatin has InChIKey MSKFOQCDNOFJAT-VCRXIKTMSA-N. Its InChI matches the owner through the double-bond layer but additionally specifies tetrahedral stereochemistry. The owner remains MSKFOQCDNOFJAT-SOFYXZRVSA-N, stereo_complete false. Exact source-product stereochemical mapping is not adjudicated here; no chemistry or xref changes. retrieved on 2026-10-09

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

Causal graph — biosynthesis 6 nodes, 6 edges

Non-native PdR/Pdx paired support of CotB4 in engineered E. coli BL21(DE3). Wild-type Pdx and engineered paper W106E (full-length canonical W107E) are different constructs using the same reference accession, not two native proteins. PdR carries the S20 Gly insertion. Whole-cell product evidence does not establish individual sufficiency, purified electron transfer, a physical complex or native partners. Existing partial-stereo chemistry and native-producer claims are unchanged.

Subject	Predicate	Object	Notes	Evidence
PdR (+Gly construct; reference accession)	with coexpressed wild-type Pdx supports	Whole-cell CotB4 with wild-type Pdx	Paired-system evidence under the stated whole-cell conditions.	DOI:10.1186/s12934-016-0487-6 https://www.uniprot.org/uniprotkb/P16640 https://www.ncbi.nlm.nih.gov/nuccore/J05406.1 https://www.ncbi.nlm.nih.gov/nuccore/D00528.1 https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT notes Whole-cell CotB4 comparison with coexpressed PdR and wild-type Pdx in engineered E. coli BL21(DE3), supplied cyclooctat-9-en-5,7-diol and a GC-MS product readout after 48 hours. The Methods describe five cultures and an empty-vector control. This establishes paired-system support, not individual sufficiency or purified electron transfer. retrieved on 2026-10-09 reference https://www.uniprot.org/uniprotkb/P16640 evidence type DATABASE_ASSERTION notes Reviewed Pseudomonas putida reference (taxon 303), camA, 422 aa; entry version 131, sequence version 1. Native camphor-system annotation is not evidence of native cyclooctatin production. This accession denotes the reference, not a separate mutant entry. retrieved on 2026-10-09 reference https://www.ncbi.nlm.nih.gov/nuccore/J05406.1 evidence type DATABASE_ASSERTION notes Deposited PdR CDS AAA25758.1; its annotated translation agrees with the selected UniProt reference. Deposit strain provenance does not establish the source strain of the synthetic 2016 construct. retrieved on 2026-10-09 reference https://www.ncbi.nlm.nih.gov/nuccore/D00528.1 evidence type DATABASE_ASSERTION notes Deposited PdR CDS BAA00413.1; its annotated translation agrees with the selected UniProt reference. Deposit strain provenance does not establish the source strain of the synthetic 2016 construct. retrieved on 2026-10-09 reference https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf evidence type CURATOR_INFERENCE notes Figure S20 literal PdR ORF is 423 aa: Gly inserted after initiator Met relative to the 422-aa P16640 reference. Both native CDSs independently translate to the reference. The synthetic construct is not identical to P16640. retrieved on 2026-10-09
Pdx (wild-type reference sequence)	with coexpressed PdR supports	Whole-cell CotB4 with wild-type Pdx	Paired-system evidence under the stated whole-cell conditions.	DOI:10.1186/s12934-016-0487-6 https://www.uniprot.org/uniprotkb/P00259 https://www.ncbi.nlm.nih.gov/nuccore/J05406.1 https://www.ncbi.nlm.nih.gov/nuccore/D00528.1 https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT notes Whole-cell CotB4 comparison with coexpressed PdR and wild-type Pdx in engineered E. coli BL21(DE3), supplied cyclooctat-9-en-5,7-diol and a GC-MS product readout after 48 hours. The Methods describe five cultures and an empty-vector control. This establishes paired-system support, not individual sufficiency or purified electron transfer. retrieved on 2026-10-09 reference https://www.uniprot.org/uniprotkb/P00259 evidence type DATABASE_ASSERTION notes Reviewed Pseudomonas putida reference (taxon 303), camB, 107 aa; entry version 144, sequence version 3. Native camphor-system annotation is not evidence of native cyclooctatin production. UniProt annotates mature chain 2..107 and a historical E/Q conflict at canonical residue 15; the selected canonical sequence contains E. No assay-host initiator-Met processing is asserted. This accession denotes the reference, not a separate mutant entry. retrieved on 2026-10-09 reference https://www.ncbi.nlm.nih.gov/nuccore/J05406.1 evidence type DATABASE_ASSERTION notes Deposited Pdx CDS AAA25759.1; its annotated translation agrees with the selected UniProt reference. Deposit strain provenance does not establish the source strain of the synthetic 2016 construct. retrieved on 2026-10-09 reference https://www.ncbi.nlm.nih.gov/nuccore/D00528.1 evidence type DATABASE_ASSERTION notes Deposited Pdx CDS BAA00414.1; its annotated translation agrees with the selected UniProt reference. Deposit strain provenance does not establish the source strain of the synthetic 2016 construct. retrieved on 2026-10-09 reference https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf evidence type CURATOR_INFERENCE notes Figure S20 literal wild-type Pdx ORF is 107 aa and equals P00259 and both independently translated native CDSs, including E at canonical position 15. This is sequence identity evidence, not native-partner evidence. retrieved on 2026-10-09
Whole-cell CotB4 with wild-type Pdx	yields	cyclooctatin (reported product)	The reported product is not asserted stereochemically identical to the partial-stereo owner and is not assigned an exact chemical identifier in this graph.	DOI:10.1186/s12934-016-0487-6 https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT notes Results report only minor cyclooctatin formation with wild-type PdR/Pdx and CotB4 under the tested conditions. The separate CotB3 comparison had no detectable diol; no general inactivity claim is made. retrieved on 2026-10-09 snippet only minor amounts of cyclooctatin reference https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf evidence type CURATOR_INFERENCE notes Figure S1b shows the wild-type PdR/Pdx condition as a low-product comparator. This is a condition-specific whole-cell product readout, not purified turnover. retrieved on 2026-10-09
PdR (+Gly construct; reference accession)	with coexpressed Pdx-W106E supports	Whole-cell CotB4 with Pdx-W106E	Paired-system evidence under the stated whole-cell conditions.	DOI:10.1186/s12934-016-0487-6 https://www.uniprot.org/uniprotkb/P16640 https://www.ncbi.nlm.nih.gov/nuccore/J05406.1 https://www.ncbi.nlm.nih.gov/nuccore/D00528.1 https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT notes Whole-cell CotB4 comparison with coexpressed PdR and Pdx-W106E in engineered E. coli BL21(DE3), supplied cyclooctat-9-en-5,7-diol and a GC-MS product readout after 48 hours. The Methods describe five cultures and an empty-vector control. This establishes paired-system support, not individual sufficiency or purified electron transfer. retrieved on 2026-10-09 reference https://www.uniprot.org/uniprotkb/P16640 evidence type DATABASE_ASSERTION notes Reviewed Pseudomonas putida reference (taxon 303), camA, 422 aa; entry version 131, sequence version 1. Native camphor-system annotation is not evidence of native cyclooctatin production. This accession denotes the reference, not a separate mutant entry. retrieved on 2026-10-09 reference https://www.ncbi.nlm.nih.gov/nuccore/J05406.1 evidence type DATABASE_ASSERTION notes Deposited PdR CDS AAA25758.1; its annotated translation agrees with the selected UniProt reference. Deposit strain provenance does not establish the source strain of the synthetic 2016 construct. retrieved on 2026-10-09 reference https://www.ncbi.nlm.nih.gov/nuccore/D00528.1 evidence type DATABASE_ASSERTION notes Deposited PdR CDS BAA00413.1; its annotated translation agrees with the selected UniProt reference. Deposit strain provenance does not establish the source strain of the synthetic 2016 construct. retrieved on 2026-10-09 reference https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf evidence type CURATOR_INFERENCE notes Figure S20 literal PdR ORF is 423 aa: Gly inserted after initiator Met relative to the 422-aa P16640 reference. Both native CDSs independently translate to the reference. The synthetic construct is not identical to P16640. retrieved on 2026-10-09
Pdx-W106E (canonical W107E; reference accession)	with coexpressed PdR supports	Whole-cell CotB4 with Pdx-W106E	Paired-system evidence under the stated whole-cell conditions.	DOI:10.1186/s12934-016-0487-6 https://www.uniprot.org/uniprotkb/P00259 https://www.ncbi.nlm.nih.gov/nuccore/J05406.1 https://www.ncbi.nlm.nih.gov/nuccore/D00528.1 https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf DOI:10.1186/s12934-016-0487-6 reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT notes Whole-cell CotB4 comparison with coexpressed PdR and Pdx-W106E in engineered E. coli BL21(DE3), supplied cyclooctat-9-en-5,7-diol and a GC-MS product readout after 48 hours. The Methods describe five cultures and an empty-vector control. This establishes paired-system support, not individual sufficiency or purified electron transfer. retrieved on 2026-10-09 reference https://www.uniprot.org/uniprotkb/P00259 evidence type DATABASE_ASSERTION notes Reviewed Pseudomonas putida reference (taxon 303), camB, 107 aa; entry version 144, sequence version 3. Native camphor-system annotation is not evidence of native cyclooctatin production. UniProt annotates mature chain 2..107 and a historical E/Q conflict at canonical residue 15; the selected canonical sequence contains E. No assay-host initiator-Met processing is asserted. This accession denotes the reference, not a separate mutant entry. retrieved on 2026-10-09 reference https://www.ncbi.nlm.nih.gov/nuccore/J05406.1 evidence type DATABASE_ASSERTION notes Deposited Pdx CDS AAA25759.1; its annotated translation agrees with the selected UniProt reference. Deposit strain provenance does not establish the source strain of the synthetic 2016 construct. retrieved on 2026-10-09 reference https://www.ncbi.nlm.nih.gov/nuccore/D00528.1 evidence type DATABASE_ASSERTION notes Deposited Pdx CDS BAA00414.1; its annotated translation agrees with the selected UniProt reference. Deposit strain provenance does not establish the source strain of the synthetic 2016 construct. retrieved on 2026-10-09 reference https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf evidence type CURATOR_INFERENCE notes Figure S20 literal wild-type Pdx ORF is 107 aa and equals P00259 and both independently translated native CDSs, including E at canonical position 15. This is sequence identity evidence, not native-partner evidence. retrieved on 2026-10-09 reference DOI:10.1186/s12934-016-0487-6 evidence type CURATOR_INFERENCE notes The Methods W106E primer maps to W107E in the full-length S20/P00259 ORF; the reference mature-chain numbering omits initiator Met. The 38-base forward primer overlaps 32 printed S20 bases and changes only that translated residue. Its terminal ATAATG extends beyond S20 and is not verified here. The published reverse primer is its reverse complement. This is a primer/sequence comparison, not independent mutant resequencing or full-plasmid verification. retrieved on 2026-10-09
Whole-cell CotB4 with Pdx-W106E	yields	cyclooctatin (reported product)	The reported product is not asserted stereochemically identical to the partial-stereo owner and is not assigned an exact chemical identifier in this graph.	DOI:10.1186/s12934-016-0487-6 https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf reference DOI:10.1186/s12934-016-0487-6 evidence type PRIMARY_EXPERIMENT notes Results report more cyclooctatin with Pdx-W106E than with wild-type Pdx; this is not a claim of superiority to AfR/Afx or a numerical fold change. retrieved on 2026-10-09 snippet also led to increased cyclooctatin formation reference https://media.springernature.com/original/springer-static/esm/art%3A10.1186%2Fs12934-016-0487-6/MediaObjects/12934_2016_487_MOESM1_ESM.pdf evidence type CURATOR_INFERENCE notes Figure S1b qualitatively places Pdx-W106E above wild-type PdR/Pdx but below AfR/Afx for the CotB4 product. Its caption names a CotB3 control despite the CotB4 panel; no normalized ratio or significance test is adopted. Tables S1/S2 duplicate D38E labels for lanes 4/5, so no lane-specific mutant assignment, densitometry or physical-complex inference is adopted. retrieved on 2026-10-09

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

Explore across X-Mech

AntibioticMech (cyclooctatin) ↗ MediaIngredientMech (naturalproductmech:mibig-3835812e03) ↗ TaxonMech: Streptomyces melanosporofaciens (NCBITaxon:67327) ↗ PathwayMech (mibig:BGC0000677) ↗

Provenance

Source concept	Source	Version
BGC0000677	MIBIG	5

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