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Details

Stereochemistry ACHIRAL
Molecular Formula C12H8S
Molecular Weight 184.257
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Dibenzothiophene

SMILES

S1C2=C(C=CC=C2)C3=C1C=CC=C3

InChI

InChIKey=IYYZUPMFVPLQIF-UHFFFAOYSA-N
InChI=1S/C12H8S/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H

HIDE SMILES / InChI

Molecular Formula C12H8S
Molecular Weight 184.257
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including "A Consumer's Dictionary of Cosmetic Ingredients: Complete Information about the Harmful and Desirable Ingredients Found in Cosmetics and Cosmeceutic" by Ruth Winter

Dibenzothiophene (DBT) is the organosulfur compound consisting of two benzene rings fused to a central thiophene ring. It is a colourless solid that is chemically somewhat similar to anthracene. This tricyclicheterocycle, and especially its alkyl substituted derivatives, occur widely in heavier fractions of petroleum. A drug that softens, separates, and causes desquamation of the cornified epithelium or horny layer of skin. DBT was used to treat acne, seborrhea and related dermatoses.

CNS Activity

Curator's Comment: CNS Neurotoxin http://mobilereagents.com/examplePages/59/59622.html https://hazmap.nlm.nih.gov/category-details?table=copytblagents&id=4737

Originator

Sources: The Chemistry of Heterocyclic Compounds, Condensed Thiophene Rings, H. D. Hartough, p. 227
Curator's Comment: Dibenzothiophene was first prepared by Stenhouse in 1870.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Uniprot: W5UCK6 (Cytochrome P450)
12.8 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 12.8 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Biodesulfurization of dibenzothiophene and other organic sulfur compounds by a newly isolated Microbacterium strain ZD-M2.
2005-06-01
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005-06
Identification of chemical substances in industrial wastes and their pyrolytic decomposition products.
2005-06
Photochemistry of substituted dibenzothiophene oxides: the effect of trapping groups.
2005-04-29
Cobalt(III) corroles as electrocatalysts for the reduction of dioxygen: reactivity of a monocorrole, biscorroles, and porphyrin-corrole dyads.
2005-04-20
Desulfurization of dibenzothiophene, benzothiophene, and other thiophene analogs by a newly isolated bacterium, Gordonia alkanivorans strain 1B.
2005-03
The effects of dimethylated and alkylated polycyclic aromatic hydrocarbons on the embryonic development of the Japanese medaka.
2005-03
Thermophilic biodesulfurization of various heterocyclic sulfur compounds and crude straight-run light gas oil fraction by a newly isolated strain Mycobacterium phlei WU-0103.
2005-02
[Selectively desulfurizing organic sulfur of diesel oil by resting cells].
2005-01
Biotechnology of desulfurization of diesel: prospects and challenges.
2005-01
Desulphurization of dibenzothiophene and diesel oils by bacteria.
2005
Biodesulfurization using Pseudomonas delafieldii in magnetic polyvinyl alcohol beads.
2005
Photochemistry and photophysics of halogen-substituted dibenzothiophene oxides.
2004-11-26
Radical cation of dibenzothiophene fully annelated with bicyclo[2.2.2]octene units: X-ray crystal structure and electronic properties.
2004-11-11
Identification and functional analysis of the genes encoding dibenzothiophene-desulfurizing enzymes from thermophilic bacteria.
2004-11
NH2-SEP-PAK cartridges for enrichment of Aromatic Sulfur Compounds from sea water: determination by GC-FID and GC-MS.
2004-10-28
Dibenzothiophene biodesulfurization pathway improvement using diagnostic GFP fusions.
2004-10-05
Crystallization and preliminary X-ray analyses of desulfurization enzyme DszB and its C27S mutant complexed with biphenyl-2-sulfinic acid.
2004-09
Thermostable flavin reductase that couples with dibenzothiophene monooxygenase, from thermophilic Bacillus sp. DSM411: purification, characterization, and gene cloning.
2004-08
Degradation of polycyclic aromatic hydrocarbons by a newly isolated dibenzofuran-utilizing Janibacter sp. strain YY-1.
2004-08
Biodegradation of polycyclic aromatic hydrocarbons by Pichia anomala.
2004-05
Defects in cardiac function precede morphological abnormalities in fish embryos exposed to polycyclic aromatic hydrocarbons.
2004-04-15
Identification of two new sets of genes for dibenzothiophene transformation in Burkholderia sp. DBT1.
2004-04
CpRu(CO)2(BF4) and [CpFe(CO)2(THF)]+ on mesoporous silica as adsorbents for the removal of dibenzothiophenes from hydrocarbon solutions.
2004-03-07
Isolation and characterization of Xanthobacter polyaromaticivorans sp. nov. 127W that degrades polycyclic and heterocyclic aromatic compounds under extremely low oxygen conditions.
2004-03
The importance of both charge exchange and proton transfer in the analysis of polycyclic aromatic compounds using atmospheric pressure chemical ionization mass spectrometry.
2004-03
Isolation of carotenoid-deficient mutant from alkylated dibenzothiophene desulfurizing nocardioform bacteria, Gordonia sp. TM414.
2004-02
Elimination of sulfur from aromatic heterocycles by a water-soluble arene ruthenium cluster: synthesis and molecular structure of [H2S2Ru4(C6H6)4]Cl2.
2004-01-21
Cloning of a gene encoding flavin reductase coupling with dibenzothiophene monooxygenase through coexpression screening using indigo production as selective indication.
2004-01-16
Evaluation of potential molecular markers for urban stormwater runoff.
2004-01
Desulfurization of dibenzothiophene by a newly isolated Corynebacterium sp. ZD-1 in aqueous phase.
2004
Toxicity of eight polycyclic aromatic compounds to red clover (Trifolium pratense), ryegrass (Lolium perenne), and mustard (Sinapsis alba).
2003-12
Deep desulfurization by selective adsorption of dibenzothiophenes on Ag+/SBA-15 and Ag+/SiO2.
2003-10-21
Effects of oil and bioremediation on mussel (Mytilus edulis L.) growth in mudflats.
2003-10
Sea breeze modulated volatilization of polycyclic aromatic hydrocarbons from the Masnou Harbor (NW Mediterranean Sea).
2003-09-01
Desulfurization of 2,4,6,8-tetraethyl dibenzothiophene by recombinant Mycobacterium sp. strain MR65.
2003-09
Analyses of microbial desulfurization reaction of alkylated dibenzothiophenes dissolved in oil phase.
2003-08-20
Enhanced desulfurization in a transposon-mutant strain of Rhodococcus erythropolis.
2003-08
Purification and characterization of the aromatic desulfinase, 2-(2'-hydroxyphenyl)benzenesulfinate desulfinase.
2003-07-01
Residue 345 of dibenzothiophene (DBT) sulfone monooxygenase is involved in C-S bond cleavage specificity of alkylated DBT sulfones.
2003-07
Recombinant Pseudomonas putida carrying both the dsz and hcu genes can desulfurize dibenzothiophene in n-tetradecane.
2003-07
Deep desulfurization of hydrodesulfurization-treated diesel oil by a facultative thermophilic bacterium Mycobacterium sp. X7B.
2003-06-27
Iron and cobalt ethylene polymerization catalysts: variations on the central donor.
2003-06-02
Anaerobic desulphurisation of thiophenes by mixed microbial communities from oilfields.
2003-06
Biodesulfurization of fossil fuels.
2003-06
Selective cleavage of 10-methyl benzo[b]naphtho[2,1-d]thiophene by recombinant Mycobacterium sp. strain.
2003-05
Cloning of a rhodococcal promoter using a transposon for dibenzothiophene biodesulfurization.
2003-02
Enhancement of phase separation by the addition of de-emulsifiers to three-phase (diesel oil/biocatalyst/aqueous phase) emulsion in diesel biodesulfurization.
2003-01
Isolation and characterization of a transposon mutant of Pseudomonas aeruginosa affecting uptake of dibenzothiophene in n-tetradecane.
2003
Origin of polycyclic aromatic hydrocarbons in lake sediments of the Mackenzie Delta.
2002-08
Patents

Sample Use Guides

Can be used in cream, lotion or soup formulations - topical application
Route of Administration: Topical
In Vitro Use Guide
Dibenzothiophene (DBT) concentrations 0, 0.1, 1, 10, 50, and 100 uM were used to determine Ethoxyresorufin-O-deethylase activities in channel catfish microsomes.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:52:52 GMT 2025
Edited
by admin
on Mon Mar 31 17:52:52 GMT 2025
Record UNII
Z3D4AJ1R48
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Dibenzothiophene
HSDB   INCI   USAN  
INCI   USAN  
Official Name English
NSC-2843
Preferred Name English
DIBENZOTHIOPHENE [IARC]
Common Name English
DIBENZOTHIOPHENE [USAN]
Common Name English
DIBENZOTHIOPHENE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78284
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
Code System Code Type Description
WIKIPEDIA
DIBENZOTHIOPHENE
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
PRIMARY
CAS
132-65-0
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID0047741
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
PRIMARY
PUBCHEM
3023
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
PRIMARY
NCI_THESAURUS
C47484
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
PRIMARY
CHEBI
23681
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PRIMARY
HSDB
7409
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PRIMARY
NSC
2843
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
PRIMARY
MESH
C016366
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-072-9
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
PRIMARY
SMS_ID
300000051336
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
PRIMARY
FDA UNII
Z3D4AJ1R48
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
PRIMARY
ChEMBL
CHEMBL219828
Created by admin on Mon Mar 31 17:52:52 GMT 2025 , Edited by admin on Mon Mar 31 17:52:52 GMT 2025
PRIMARY