8-azaguanine
CHEBI:63486 EXACT SEEDED cytotoxicenzyme inhibitor
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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 triazolopyrimidine that consists of 3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidine bearing amino and oxo substituents at positions 5 and 7 respectively.
Structure
| Standard InChIKey | LPXQRXLUHJKZIE-UHFFFAOYSA-N |
|---|---|
| SMILES | C12=NNN=C1N=C(NC2=O)N |
| Stereochemistry | fully defined |
| Cross-references | pubchem:135403646 |
Filing pathway
Alkaloids — 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 other, 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 pathocidini NCBITaxon:1650571 |
SOURCE_ASSERTION | mibig:BGC0002508 | PMID:32235841 |
Occurrences 0
None cited.
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0002508 | Streptomyces pathocidini NCBITaxon:1650571 |
CLUSTER_DEMONSTRATED | genbank:MT543149.1 |
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.
Mechanism & Biosynthesis Overview
Causal graph — biosynthesis 10 nodes, 9 edges
Bounded genetic evidence for native-reference 8-AzgD/E/F in Streptomyces pathocidini CGMCC4.1633 (named S. albus subsp. pathocidicus in Hou et al.). The three deletion interventions and their product phenotypes are distinct from the encoded proteins. Main article and Figures 1/2 inspected; supplements and exact mutant constructs were not. CHEBI:63486 is the neutral free-base compound anchor, not an experimentally resolved solution tautomer or protonation state. No catalytic reaction, physical complex, universal necessity, other-strain Ptn equivalence, or producer/BGC evidence upgrade is asserted.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| CGMCC4.1633 8-azgD deletion | deletes_gene_represented_by | 8-AzgD (CGMCC4.1633 native reference) | The identifier denotes the deposited native gene product, not an intact protein present in the deletion strain or a sequenced mutant allele. No equivalent UniProt reference or other-strain Ptn protein is substituted. | DOI:10.3389/fbioe.2020.603514 |
| CGMCC4.1633 8-azgD deletion | has_reported_trace_amount_of | 8-azaguanine | Figure 2A, trace v: trace product remains. This is not complete abolition, a numerical yield or a purified-enzyme reaction. Accumulated nucleoside congeners are not merged into the free-base owner. | DOI:10.3389/fbioe.2020.603514
|
| CGMCC4.1633 8-azgE deletion | deletes_gene_represented_by | 8-AzgE (CGMCC4.1633 native reference) | The identifier denotes the deposited native gene product, not an intact protein present in the deletion strain or a sequenced mutant allele. No equivalent UniProt reference or other-strain Ptn protein is substituted. | DOI:10.3389/fbioe.2020.603514 |
| CGMCC4.1633 8-azgE deletion | has_reported_trace_amount_of | 8-azaguanine | Figure 2A, trace vi: trace product remains. This is not complete abolition, a numerical yield or a purified-enzyme reaction. Accumulated nucleoside congeners are not merged into the free-base owner. | DOI:10.3389/fbioe.2020.603514
|
| CGMCC4.1633 8-azgF deletion | deletes_gene_represented_by | 8-AzgF (CGMCC4.1633 native reference) | The identifier denotes the deposited native gene product, not an intact protein present in the deletion strain or a sequenced mutant allele. No equivalent UniProt reference or other-strain Ptn protein is substituted. | DOI:10.3389/fbioe.2020.603514 |
| CGMCC4.1633 8-azgF deletion | has_reported_loss_of_detectable | 8-azaguanine | Figure 2A, trace vii versus wild type i and authentic standard: reported loss of detectable 8-azaguanine under the study conditions. No numerical detection limit, absolute zero, general essentiality or directly measured GTP reaction is asserted. | DOI:10.3389/fbioe.2020.603514
|
| 8-AzgD (CGMCC4.1633 native reference) | has a sequence-identical UniProtKB example | 8-AzgD (S. pathocidini ACH429_00980 UniProtKB example) | UniProtKB:A0A6G9KJ81 is the active Streptomyces pathocidini (ACH429_00980) entry sharing 100% amino-acid sequence identity (UPI000B1A84C6) with MT543149.1 QLM04718.1 (8-AzgD). | https://www.uniprot.org/uniprotkb/A0A6G9KJ81 |
| 8-AzgE (CGMCC4.1633 native reference) | has a sequence-identical UniProtKB example | 8-AzgE (S. pathocidini ACH429_00985 UniProtKB example) | UniProtKB:A0A7G3ZQC3 is the active Streptomyces pathocidini (ACH429_00985) entry sharing 100% amino-acid sequence identity (UPI0006E3F696) with MT543149.1 QLM04711.1 (8-AzgE). | https://www.uniprot.org/uniprotkb/A0A7G3ZQC3 |
| 8-AzgF (CGMCC4.1633 native reference) | has a sequence-identical UniProtKB example | 8-AzgF (S. pathocidini ACH429_00990 UniProtKB example) | UniProtKB:A0A6G9KIY0 is the active Streptomyces pathocidini (ACH429_00990) entry sharing 100% amino-acid sequence identity (UPI00099E5E15) with MT543149.1 QLM04712.1 (8-AzgF). | https://www.uniprot.org/uniprotkb/A0A6G9KIY0 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Causal graph — biosynthesis 9 nodes, 8 edges
Bounded native genetic evidence for 8-AzgA/B/G in Streptomyces pathocidini CGMCC4.1633, named S. albus subsp. pathocidicus in Hou et al. Deletion interventions are separate from deposited protein references. The previously archived main text and Figures 1/2 were inspected; supplements and exact mutant constructs remain uninspected. This graph records reduced-product phenotypes, not A nitric-oxide enzyme activity, B nitrogen-species transport, G radical chemistry, physical assembly or other-strain Ptn equivalence. CHEBI:63486 anchors the neutral free base, not a resolved solution microspecies. Existing D/E/F evidence and all source-owned claims are retained separately.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| CGMCC4.1633 8-azgA deletion | deletes_gene_represented_by | 8-AzgA (CGMCC4.1633 native reference) | The identifier denotes a deposited native gene product, not an intact protein in the deletion strain or an independently sequenced mutant allele. No UniProt homolog or other-strain Ptn protein is substituted. | DOI:10.3389/fbioe.2020.603514 |
| CGMCC4.1633 8-azgA deletion | has_reported_reduced_amount_of | 8-azaguanine | Figure 2A trace iii, compared with wild type i and authentic standard viiii. The Results report lower product under these culture conditions, not abolition. No percentage, absolute yield, statistical significance, universal necessity or direct catalytic activity is inferred from peak height. | DOI:10.3389/fbioe.2020.603514
|
| CGMCC4.1633 8-azgB deletion | deletes_gene_represented_by | 8-AzgB (CGMCC4.1633 native reference) | The identifier denotes a deposited native gene product, not an intact protein in the deletion strain or an independently sequenced mutant allele. UniParc UPI0006E298C9 links inactive S. pathocidini TrEMBL A0A6G9KGR0; no homolog substituted. | DOI:10.3389/fbioe.2020.603514 |
| CGMCC4.1633 8-azgB deletion | has_reported_reduced_amount_of | 8-azaguanine | Figure 2A trace iv, compared with wild type i and authentic standard viiii. The Results report lower product under these culture conditions, not abolition. No percentage, absolute yield, statistical significance, universal necessity or direct catalytic activity is inferred from peak height. | DOI:10.3389/fbioe.2020.603514
|
| CGMCC4.1633 8-azgG deletion | deletes_gene_represented_by | 8-AzgG (CGMCC4.1633 native reference) | The identifier denotes a deposited native gene product, not an intact protein in the deletion strain or an independently sequenced mutant allele. No UniProt homolog or other-strain Ptn protein is substituted. | DOI:10.3389/fbioe.2020.603514 |
| CGMCC4.1633 8-azgG deletion | has_reported_reduced_amount_of | 8-azaguanine | Figure 2A trace viii, compared with wild type i and authentic standard viiii. The Results report lower product under these culture conditions, not abolition. No percentage, absolute yield, statistical significance, universal necessity or direct catalytic activity is inferred from peak height. | DOI:10.3389/fbioe.2020.603514
|
| 8-AzgA (CGMCC4.1633 native reference) | has a sequence-identical UniProtKB example | 8-AzgA (S. pathocidini ACH429_00965 UniProtKB example) | UniProtKB:A0A6G9KI63 is the active Streptomyces pathocidini (ACH429_00965) entry sharing 100% amino-acid sequence identity (UPI000A88606E) with MT543149.1 QLM04708.1 (8-AzgA). | https://www.uniprot.org/uniprotkb/A0A6G9KI63 |
| 8-AzgG (CGMCC4.1633 native reference) | has a sequence-identical UniProtKB example | 8-AzgG (S. pathocidini ACH429_00995 UniProtKB example) | UniProtKB:A0A7G3ZQC5 is the active Streptomyces pathocidini (ACH429_00995) entry sharing 100% amino-acid sequence identity (UPI0006E15438) with MT543149.1 QLM04713.1 (8-AzgG). | https://www.uniprot.org/uniprotkb/A0A7G3ZQC5 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Causal graph — biosynthesis 13 nodes, 12 edges
Reported native genetic-test outcomes for 8-AzgC/H/I/J/K in Streptomyces pathocidini CGMCC4.1633, named S. albus subsp. pathocidicus in Hou et al. C/H/J deletions have reported reduced product, K a small increase, and I no reported change. I is included to preserve the negative experimental context, not to assign a positive biosynthetic function. Deletion interventions are distinct from deposited protein references. Evidence is the archived main-text Methods/Results; supplementary Figure 4 and PCR data remain uninspected. No catalytic reaction, transcriptional regulation, physical assembly, general essentiality/dispensability, J1074 equivalence or producer/BGC upgrade is asserted. CHEBI:63486 denotes the neutral free base, not a resolved solution tautomer or protonation state.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| CGMCC4.1633 8-azgC deletion | deletes_gene_represented_by | 8-AzgC (CGMCC4.1633 native reference) | The accession denotes the deposited native gene product, not an intact protein in the deletion strain or an independently sequenced mutant allele. No exact UniProt mapping was established by the archived identifier-specific query; no homolog or other-strain Ptn protein is substituted. | DOI:10.3389/fbioe.2020.603514 |
| CGMCC4.1633 8-azgC deletion | has_reported_reduced_amount_of | 8-azaguanine | The Results report lower 8-azaguanine in this individual mutant fermentation broth relative to wild type. This is a qualitative main-text report, not abolition, a quantified yield, statistical significance or a catalytic assignment. | DOI:10.3389/fbioe.2020.603514
|
| CGMCC4.1633 8-azgH deletion | deletes_gene_represented_by | 8-AzgH (CGMCC4.1633 native reference) | The accession denotes the deposited native gene product, not an intact protein in the deletion strain or an independently sequenced mutant allele. No exact UniProt mapping was established by the archived identifier-specific query; no homolog or other-strain Ptn protein is substituted. | DOI:10.3389/fbioe.2020.603514 |
| CGMCC4.1633 8-azgH deletion | has_reported_reduced_amount_of | 8-azaguanine | The Results report lower 8-azaguanine in this individual mutant fermentation broth relative to wild type. This is a qualitative main-text report, not abolition, a quantified yield, statistical significance or a catalytic assignment. | DOI:10.3389/fbioe.2020.603514
|
| CGMCC4.1633 8-azgI deletion | deletes_gene_represented_by | 8-AzgI (CGMCC4.1633 native reference) | The accession denotes the deposited native gene product, not an intact protein in the deletion strain or an independently sequenced mutant allele. UniParc UPI001862886B links inactive S. pathocidini TrEMBL A0A7G3ZQC7 (zero active UniProtKB xrefs); no homolog substituted. | DOI:10.3389/fbioe.2020.603514 |
| CGMCC4.1633 8-azgI deletion | has_reported_no_change_in_amount_of | 8-azaguanine | The Results report no effect on 8-azaguanine production after this deletion under the tested conditions. Included as an explicit negative genetic-test context, not a positive biosynthetic role or causal effect. No equivalence margin, detection power, universal dispensability or biochemical function is established by this report. | DOI:10.3389/fbioe.2020.603514
|
| CGMCC4.1633 8-azgJ deletion | deletes_gene_represented_by | 8-AzgJ (CGMCC4.1633 native reference) | The accession denotes the deposited native gene product, not an intact protein in the deletion strain or an independently sequenced mutant allele. UniParc UPI00185FCABD links inactive S. pathocidini TrEMBL A0A7G3ZQC8 (zero active UniProtKB xrefs); no homolog substituted. | DOI:10.3389/fbioe.2020.603514 |
| CGMCC4.1633 8-azgJ deletion | has_reported_reduced_amount_of | 8-azaguanine | The Results report lower 8-azaguanine in this individual mutant fermentation broth relative to wild type. This is a qualitative main-text report, not abolition, a quantified yield, statistical significance or a catalytic assignment. | DOI:10.3389/fbioe.2020.603514
|
| CGMCC4.1633 8-azgK deletion | deletes_gene_represented_by | 8-AzgK (CGMCC4.1633 native reference) | The accession denotes the deposited native gene product, not an intact protein in the deletion strain or an independently sequenced mutant allele. UniParc UPI0006E35D5C links inactive S. pathocidini TrEMBL A0A7G3ZQC9 (ACH429_01015) (active UniProtKB xrefs are other Streptomyces spp.); no homolog substituted. | DOI:10.3389/fbioe.2020.603514 |
| CGMCC4.1633 8-azgK deletion | has_reported_small_increase_in_amount_of | 8-azaguanine | The Results report a small increase in 8-azaguanine titer after this deletion. The article interprets K as a negative transcriptional regulator, but the genetic phenotype alone does not establish that mechanism; it is not adopted here. The deposited glycosyltransferase annotation is not an enzyme assay. No numerical increase or statistical significance is asserted. | DOI:10.3389/fbioe.2020.603514
|
| 8-AzgC (CGMCC4.1633 native reference) | has a sequence-identical UniProtKB example | 8-AzgC (S. pathocidini ACH429_00975 UniProtKB example) | UniProtKB:A0A6G9KI21 is the active Streptomyces pathocidini (ACH429_00975) entry sharing 100% amino-acid sequence identity (UPI0006E1F3FA) with MT543149.1 QLM04710.1 (8-AzgC). | https://www.uniprot.org/uniprotkb/A0A6G9KI21 |
| 8-AzgH (CGMCC4.1633 native reference) | has a sequence-identical UniProtKB example | 8-AzgH (S. pathocidini ACH429_01000 UniProtKB example) | UniProtKB:A0A7G3ZQC6 is the active Streptomyces pathocidini (ACH429_01000) entry sharing 100% amino-acid sequence identity (UPI000B2DAD11) with MT543149.1 QLM04714.1 (8-AzgH). | https://www.uniprot.org/uniprotkb/A0A7G3ZQC6 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Bioactivities 25
Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.
| Assay | Result | Target enzyme | Source detail |
|---|---|---|---|
| A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. | OTHER 0.2909 uM; NOT_DETERMINED | Not recorded | pubchem.aid:624296
|
| A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | OTHER 14.581 uM; NOT_DETERMINED | Not recorded | pubchem.aid:624297
|
| Confirmation and Secondary Assays for Modulators of Hemoglobin Beta Chain Splicing at IVS2 654 and 705 loci | OTHER 2.51189 uM; ACTIVE | Not recorded | pubchem.aid:1405
|
| Counterscreen for activators of the function of SWI/SNF related, matrix associated, actin dependent regulator of chromatin, subfamily a, member 2 (SMARCA2, BRM): Luminescence-based cell-based high throughput dose response assay to identify non-selective compounds using the VP16 reporter assay | EC50 91.17 uM; INACTIVE | Not recorded | pubchem.aid:686995
|
| Dose Response selectivity of uHTS chemical inhibitors of T-cell specific antigen receptor-induced NF-kB activation in a 697B cell line using a luminescence assay | IC50 2.56 uM; ACTIVE | Not recorded | pubchem.aid:489033
|
| Dose response confirmation of uHTS chemical inhibitors of T-cell specific antigen receptor-induced NF-kB activation in a Jurkat cell line using a luminescence assay | IC50 80 uM; INACTIVE | Not recorded | pubchem.aid:489035
|
| Dose response counterscreen of uHTS chemical inhibitors of T-cell specific antigen receptor-induced NF-kB activation in a HEK-293T cell line using a luminescence assay | IC50 80 uM; INACTIVE | Not recorded | pubchem.aid:489041
|
| Dose response cytotoxicity of uHTS chemical inhibitors of T-cell specific antigen receptor-induced NF-kB activation in a HEK-293T cell line using a luminescence assay | IC50 80 uM; INACTIVE | Not recorded | pubchem.aid:489026
|
| Luminescence Cell-Based Dose Response HTS Screen to Identify Cytotoxic Compounds of NIH3T3 cells. | EC50 10.345 uM; ACTIVE | Not recorded | pubchem.aid:2010
|
| Luminescence Cell-Based/Microorganism Dose Confirmation HTS to Identify Inhibitors of T.Cruzi Replication. | EC50 0.1 uM; ACTIVE | Not recorded | pubchem.aid:2044
|
| Luminescence Cell-Based/Microorganism Primary HTS to Identify Inhibitors of T.Cruzi Infection | EC50 0.153 uM; ACTIVE | Not recorded | pubchem.aid:2294
|
| Luminescence-based cell-based high throughput dose response assay to identify activators of the function of SWI/SNF related, matrix associated, actin dependent regulator of chromatin, subfamily a, member 2 (SMARCA2, BRM) | EC50 91.17 uM; INACTIVE | Not recorded | pubchem.aid:686991
|
| MITF Measured in Cell-Based System Using Plate Reader - 2084-01_Inhibitor_DoseNoFile_CherryPick_Activity_Set2 | OTHER 0.875 uM; ACTIVE | Not recorded | pubchem.aid:493177
|
| MITF Measured in Cell-Based System Using Plate Reader - 2084-01_Inhibitor_DoseNoFile_CherryPick_Activity_Set3 | OTHER 0.875 uM; ACTIVE | Not recorded | pubchem.aid:493073
|
| MITF Measured in Cell-Based System Using Plate Reader - 2084-01_Inhibitor_DoseNoFile_CherryPick_Activity_Set4 | OTHER 0.875 uM; ACTIVE | Not recorded | pubchem.aid:493102
|
| Nrf2 qHTS screen for inhibitors | OTHER 29.0929 uM; NOT_DETERMINED | Not recorded | pubchem.aid:504444
|
| Total Fluorescence Counterscreen for Inhibitors of the Interaction of Thyroid Hormone Receptor and Steroid Receptor Coregulator 2 | OTHER 79.4328 uM; NOT_DETERMINED | Not recorded | pubchem.aid:1479
|
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | OTHER 11.2202 uM; NOT_DETERMINED | Not recorded | pubchem.aid:1645883
|
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | OTHER 11.2202 uM; NOT_DETERMINED | UniProtKB:O95398 | pubchem.aid:1645883
|
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | OTHER 125.892 uM; NOT_DETERMINED | Not recorded | pubchem.aid:1645883
|
| Validation qHTS for agonist of cAMP-regulated guanine nucleotide exchange factor 3 (EPAC1) | OTHER 125.892 uM; NOT_DETERMINED | UniProtKB:O95398 | pubchem.aid:1645883
|
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | OTHER 0.4467 uM; NOT_DETERMINED | Not recorded | pubchem.aid:1645886
|
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | OTHER 0.4467 uM; NOT_DETERMINED | UniProtKB:Q8WZA2 | pubchem.aid:1645886
|
| Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | OTHER 0.1259 uM; NOT_DETERMINED | Not recorded | PMID:35787375
|
| Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | OTHER 0.1259 uM; NOT_DETERMINED | UniProtKB:Q99700 | PMID:35787375
|
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Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0002508 | MIBIG | 2 |
| CHEBI:63486 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/8-azaguanine.yaml, which is generated from the committed inventories. Neither is edited by hand.