AntibioticMech

hexachlorophene

CHEBI:5693 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An organochlorine compound that is diphenylmethane in which each of the phenyl groups is substituted by chlorines at positions 2, 3, and 5, and by a hydroxy group at position 6. An antiseptic that is effective against Gram-positive organisms, it is used in soaps and creams for the treatment of various skin disorders. It is also used in agriculture as an acaricide and fungicide, but is not approved for such use within the European Union. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Chemical structure

Computed structure properties
Molecular formulaC13H6Cl6O2
Charge0
Average mass406.907 Da
Monoisotopic mass403.8499 Da
SourceChEBI
InChIKeyACGUYXCXAPNIKK-UHFFFAOYSA-N

SMILES

Oc1c(Cl)cc(Cl)c(Cl)c1Cc1c(O)c(Cl)cc(Cl)c1Cl

InChI

InChI=1S/C13H6Cl6O2/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3-9(17)13(5)21/h2-3,20-21H,1H2

Also called

Cross-references

Equivalent identifiers for this same structure in other resources.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
SourceNative IDLabelMinted CURIEVersion
CHEBI CHEBI:5693 hexachlorophene antibioticmech:chebi-81e9dce2c3 2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

Replicase polyprotein 1a VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).

Severe acute respiratory syndrome coronavirus NCBITaxon:2901879

Quantitative measurements
TypeReported valueAssayBindingDB IDsReference
KI 4000 nM Determination of kinetic parameters and the Ki of effective compounds using the FRET peptide
Kinetic parameters were obtained using various concentrations of FRET peptide in the fluorescent assay. The maximal velocity (Vmax) and Michaelis Menten constant (Km) were calculated from the Eadie Hofstee plot. If the type of inhibitionwas found to be competitive using a Lineweaver Burk double reciprocal plot, then the inhibitory constant (Ki) for 3CLpro was estimated using the equation:Ki = IC50/(1+[substrate]/Km).Plots were performed, and kinetic parameters were calculated, using Prism software (Graphpad Software, San Diego, CA).		 RSID 844294
assay 8809_1
monomer 31712		 PMID:15950190
Organism-specific examples
ProteinGeneOrganismEntry
Replicase polyprotein 1a UniProtKB:P0C6U8 — Severe acute respiratory syndrome coronavirus REVIEWED

Replicase polyprotein 1ab VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).

Severe acute respiratory syndrome coronavirus 2 NCBITaxon:2697049

Quantitative measurements
TypeReported valueAssayBindingDB IDsReference
IC50 21520 nM 3CLpro enzyme assay
The 3CLpro enzyme assay was developed in 384-well black, medium binding microplates (Greiner Bio-One, Monroe, NC, USA) with a total volume of 20 μL and then miniaturized to 1536-well format. In 384-well plate format, 10 μL enzyme in reaction buffer was added into each well, followed by the addition of 10 μL substrate. Fluorescent intensity was measured at different time points on a PHERAstar FSX plate reader (BMG Labtech, Cary, NC, USA) with Ex=340 nm/Em=460 nm after the addition of substrate. The experiment was conducted at both room temperature (RT) and 37 °C.Steady-state kinetic parameters were evaluated using 50 nM 3CLpro and different concentrations of substrate. In brief, 10 μL/well enzyme was added into 384-well plate. The reaction was then initialized by adding the substrate solutions at different concentrations. The substrate stock solution was serially diluted 1:2 to obtain seven concentrations. The final concentrations used in this test were 160, 80, 40, 20, 10, 5, and 2.5 μM. The fluorescent intensity was measured at 5, 10, 15, and 30 min.		 RSID 844363
assay 8814_1
monomer 31712		 PMID:32803196
EC50 790 nM SARS-CoV-2 CPE assay
SARS-CoV-2 CPE assay was conducted at Southern Research Institute (Birmingham, AL) as described in previous reports30, 31. In brief, high ACE2 expressing Vero E6 cells were inoculated with SARS-CoV-2 (USA_WA1/2020) at 0.002 M.O.I. After infection of 72 h at 37 °C and 5% CO2, the cell viability was examined with CellTiter-Glo ATP content assay kit (Promega, Madison, WI, USA). CPE raw data were normalized to non-infected cells and virus infected cells only which were set as 100% efficacy and 0 efficacy, respectively. In addition, the compound cytotoxicity was evaluated in the same cells by measuring ATP content in the absence of virus.		 RSID 844364
assay 8814_2
monomer 31712		 PMID:32803196
IC50 900 nM DRC analysis by immunofluorescence
Ten-point DRCs were generated for each drug. Vero cells were seeded at 1.2 × 104 cells per well in DMEM, supplemented with 2% FBS and 1× antibiotic-antimycotic solution (Gibco), in black, 384-well μClear plates (Greiner Bio-One) 24 h prior to the experiment. Ten-point DRCs were generated, with compound concentrations ranging from 0.1 to 50 μM. For the viral infections, plates were transferred into the BSL3 containment facility and SARS-CoV-2 was added at a multiplicity of infection (MOI) of 0.0125. The cells were fixed at 24 hours postinfection (hpi) with 4% PFA and analyzed by immunofluorescence. The acquired images were analyzed using in-house software to quantify cell numbers and infection ratios, and antiviral activity was normalized to positive (mock) and negative (0.5% DMSO) controls in each assay plate. DRCs were fitted by sigmoidal dose-response models, with the following equation: Y = bottom + (top − bottom)/[1 + (IC50/X)Hillslope], using XLfit 4 software or Prism7. IC50 values were calculated from the normalized activity data set-fitted curves. All IC50 and 50% cytotoxic concentration (CC50) values were measured in duplicate, and the quality of each assay was controlled by Z -factor and the coefficient of variation in percent (%CV).		 RSID 874414
assay 8945_1
monomer 31712		 PMID:32366720
IC50 21520 nM Various Assay
This is a review article. Please point to the original journal.		 RSID 1074182
assay 10079_1
monomer 31712		 PMID:34798775
Organism-specific examples
ProteinGeneOrganismEntry
Replicase polyprotein 1ab UniProtKB:P0DTD1 — Severe acute respiratory syndrome coronavirus 2 REVIEWED

Replicase polyprotein 1ab VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).

Severe acute respiratory syndrome coronavirus NCBITaxon:2901879

Quantitative measurements
TypeReported valueAssayBindingDB IDsReference
IC50 13700 nM Various Assay
This is a review article. Please point to the original journal.		 RSID 1074119
assay 10079_1
monomer 31712		 PMID:34798775
Organism-specific examples
ProteinGeneOrganismEntry
Replicase polyprotein 1ab UniProtKB:P0C6X7 — Severe acute respiratory syndrome coronavirus REVIEWED

Mechanism summary

Clinical status
APPROVED

Curation history

  1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Seeded from data/raw/ inventories (CHEBI)

  2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  5. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  6. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.