chloramphenicol

naturalproductmech:mibig-d9dc3ff908 MINTED SEEDED enzyme inhibitor

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	WIIZWVCIJKGZOK-UHFFFAOYSA-N
SMILES	OCC(NC(=O)C(Cl)Cl)C(O)C1=CC=C(C=C1)N(=O)=O
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	npatlas:NPA016373, pubchem:5959

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 nrps, 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 ATCC 10712 NCBITaxon:953739	BGC_CHARACTERIZED	mibig:BGC0000893	PMID:11577160

Occurrences 1

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 venezuelae NCBITaxon:54571	LOTUS	DOI:10.1021/JA01175A065

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000893	Streptomyces venezuelae ATCC 10712 NCBITaxon:953739	CLUSTER_DEMONSTRATED	genbank:FR845719.1

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	CmlI UniProtKB:F2RB83	RHEA:58884	CHEBI:47325 → CHEBI:17698	DOI:10.1016/j.tet.2012.06.036

Step 1: CmlI is the BGC0000893 SVEN_0924 arylamine N-oxygenase. RHEA:58884 captures the six-electron oxidation of alpha-N-dichloroacetyl-p-aminophenylserinol to exact stereochemical CHEBI:17698 chloramphenicol with AH2 and O2 as cosubstrates; the record remains minted because MIBiG BGC0000893 preserves a stereochemically incomplete chloramphenicol structure.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Terminal chloramphenicol N-oxygenation by S. venezuelae ATCC 10712 CmlI, represented with the exact ChEBI-stereochemical Rhea substrate and product although the seeded MIBiG record is stereo-incomplete.

Subject	Predicate	Object	Notes	Evidence
alpha-N-dichloroacetyl-p-aminophenylserinol	is N-oxygenated by	CmlI	The arylamine precursor, commonly abbreviated NH2-CAM, is oxidized by CmlI.	DOI:10.1016/j.tet.2012.06.036 DOI:10.1021/acs.biochem.7b00695 reference DOI:10.1016/j.tet.2012.06.036 evidence type PRIMARY_EXPERIMENT snippet CmlI is an N-oxygenase in the biosynthesis of chloramphenicol notes Biochemical reconstitution connected CmlI to the conversion of NH2-CAM into chloramphenicol. reference DOI:10.1021/acs.biochem.7b00695 evidence type PRIMARY_EXPERIMENT snippet CmlI N-Oxygenase Catalyzes the Final Three Steps in Chloramphenicol Biosynthesis notes Transient kinetic experiments supported CmlI retention of hydroxylamine and nitroso intermediates during the six-electron oxidation.
CmlI	forms	chloramphenicol	CmlI catalyzes the N-oxygenation sequence that forms the aryl-nitro group of chloramphenicol.	DOI:10.1016/j.tet.2012.06.036 DOI:10.1021/acs.biochem.7b00695 reference DOI:10.1016/j.tet.2012.06.036 evidence type PRIMARY_EXPERIMENT snippet CmlI is an N-oxygenase in the biosynthesis of chloramphenicol notes Biochemical reconstitution connected CmlI to the conversion of NH2-CAM into chloramphenicol. reference DOI:10.1021/acs.biochem.7b00695 evidence type PRIMARY_EXPERIMENT snippet CmlI N-Oxygenase Catalyzes the Final Three Steps in Chloramphenicol Biosynthesis notes Transient kinetic experiments supported CmlI retention of hydroxylamine and nitroso intermediates during the six-electron oxidation.

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.

Explore across X-Mech

AntibioticMech (chloramphenicol) ↗ MediaIngredientMech (naturalproductmech:mibig-d9dc3ff908) ↗ TaxonMech: Streptomyces venezuelae ATCC 10712 (NCBITaxon:953739) ↗ PathwayMech (mibig:BGC0000893) ↗

Provenance

Source concept	Source	Version
BGC0000893	MIBIG	5

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

Assay	Result	Target enzyme	Source detail
5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assay	OTHER 61.6448 uM; INACTIVE	Not recorded	pubchem.aid:1963587 assay 5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assay evidence reference pubchem.aid:1963587 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1963587, deposited by 824; assay type Confirmatory. Source endpoint: Potency. call INACTIVE measurement type OTHER value 61.6448 units uM
5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assay	OTHER 61.6448 uM; INACTIVE	Not recorded	pubchem.aid:1963587 assay 5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assay evidence reference pubchem.aid:1963587 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1963587, deposited by 824; assay type Confirmatory. Source endpoint: Potency. Target accession AAH96839 was left ungrounded because PubChem did not provide a UniProtKB accession. call INACTIVE measurement type OTHER value 61.6448 units uM
5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assay	OTHER 0.0133 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1963586 assay 5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assay evidence reference pubchem.aid:1963586 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1963586, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 0.0133 units uM
5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assay	OTHER 0.0133 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1963586 assay 5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assay evidence reference pubchem.aid:1963586 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1963586, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AAH96839 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 0.0133 units uM
A Counter Screen to identiry small molecule screen for inhibitors of the PhoP regulon in Salmonella Typhimurium	IC50 9.59 uM; ACTIVE	Not recorded	pubchem.aid:2401 assay A Counter Screen to identiry small molecule screen for inhibitors of the PhoP regulon in Salmonella Typhimurium evidence reference pubchem.aid:2401 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2401, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type IC50 value 9.59 units uM activity class ENZYME_INHIBITOR
A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology	OTHER 39.8107 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1645839 assay A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology evidence reference pubchem.aid:1645839 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1645839, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 39.8107 units uM
A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology	OTHER 39.8107 uM; NOT_DETERMINED	UniProtKB:O14656	pubchem.aid:1645839 assay A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology evidence reference pubchem.aid:1645839 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1645839, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 39.8107 units uM target enzyme UniProtKB:O14656
A counter screen for small molecule screen for inhibitors of the PhoP regulon in Salmonella typhi	IC50 1.57 uM; ACTIVE	Not recorded	pubchem.aid:2384 assay A counter screen for small molecule screen for inhibitors of the PhoP regulon in Salmonella typhi evidence reference pubchem.aid:2384 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2384, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type IC50 value 1.57 units uM activity class ENZYME_INHIBITOR
A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells.	OTHER 0.0052 uM; NOT_DETERMINED	Not recorded	pubchem.aid:624296 assay A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. evidence reference pubchem.aid:624296 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624296, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession NP_056979 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 0.0052 units uM
A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells.	OTHER 0.0058 uM; INACTIVE	Not recorded	pubchem.aid:624297 assay A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. evidence reference pubchem.aid:624297 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624297, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency. Target accession NP_056979 was left ungrounded because PubChem did not provide a UniProtKB accession. call INACTIVE measurement type OTHER value 0.0058 units uM
A screen for inhibitors of the PhoP regulon in Salmonella Typhi using a modified counterscreen	IC50 2.713 uM; ACTIVE	Not recorded	pubchem.aid:1985 assay A screen for inhibitors of the PhoP regulon in Salmonella Typhi using a modified counterscreen evidence reference pubchem.aid:1985 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1985, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type IC50 value 2.713 units uM activity class ENZYME_INHIBITOR
A screen for inhibitors of the PhoP regulon in Salmonella Typhimurium using a modified counterscreen.	IC50 8.46 uM; ACTIVE	Not recorded	pubchem.aid:1981 assay A screen for inhibitors of the PhoP regulon in Salmonella Typhimurium using a modified counterscreen. evidence reference pubchem.aid:1981 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1981, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type IC50 value 8.46 units uM activity class ENZYME_INHIBITOR
A small molecule screen for inhibitors of the PhoP regulon in Salmonella Typhimurium	IC50 9.52 uM; ACTIVE	Not recorded	pubchem.aid:1863 assay A small molecule screen for inhibitors of the PhoP regulon in Salmonella Typhimurium evidence reference pubchem.aid:1863 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1863, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type IC50 value 9.52 units uM activity class ENZYME_INHIBITOR
A small molecule screen for inhibitors of the PhoP regulon in Salmonella typhi	IC50 4.85 uM; ACTIVE	Not recorded	pubchem.aid:1850 assay A small molecule screen for inhibitors of the PhoP regulon in Salmonella typhi evidence reference pubchem.aid:1850 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1850, deposited by Southern Research Specialized Biocontainment Screening Center; assay type Confirmatory. call ACTIVE measurement type IC50 value 4.85 units uM activity class ENZYME_INHIBITOR
Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay	OTHER 13.6854 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1963593 assay Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay evidence reference pubchem.aid:1963593 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1963593, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 13.6854 units uM
Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay	OTHER 13.6854 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1963593 assay Adrenergic beta2 receptor (ADRB2) small molecule agonists, cell-based qHTS assay evidence reference pubchem.aid:1963593 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1963593, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession NP_000015 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 13.6854 units uM
Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen	OTHER 24.3365 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1346981 assay Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen evidence reference pubchem.aid:1346981 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1346981, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 24.3365 units uM
Cholinergic receptor muscarinic 1 (CHRM1) small molecule antagonists, cell-based qHTS assay	OTHER 3.7501 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1963588 assay Cholinergic receptor muscarinic 1 (CHRM1) small molecule antagonists, cell-based qHTS assay evidence reference pubchem.aid:1963588 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1963588, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 3.7501 units uM
Cholinergic receptor muscarinic 1 (CHRM1) small molecule antagonists, cell-based qHTS assay	OTHER 3.7501 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1963588 assay Cholinergic receptor muscarinic 1 (CHRM1) small molecule antagonists, cell-based qHTS assay evidence reference pubchem.aid:1963588 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1963588, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession NP_000729 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 3.7501 units uM
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay	OTHER 35.5742 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1671199 assay Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671199 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671199, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 35.5742 units uM
Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay	OTHER 35.5742 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1671199 assay Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671199 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671199, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession EAW99313 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 35.5742 units uM
Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay	OTHER 4.4785 uM; ACTIVE	Not recorded	pubchem.aid:1671197 assay Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671197 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671197, deposited by 824; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 4.4785 units uM
Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay	OTHER 4.4785 uM; ACTIVE	Not recorded	pubchem.aid:1671197 assay Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671197 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671197, deposited by 824; assay type Confirmatory. Source endpoint: Potency. Target accession AAV41877 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type OTHER value 4.4785 units uM
Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assay	OTHER 31.7055 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1671198 assay Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671198 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671198, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 31.7055 units uM
Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assay	OTHER 31.7055 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1671198 assay Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assay evidence reference pubchem.aid:1671198 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1671198, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AGS09764 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 31.7055 units uM notes 166 further PubChem assay results are in data/raw/pubchem_bioassay.tsv but not written here.