NP-MRD: Showing NP-Card for dibenzothiophene (NP0262460)

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Record Information

Version

2.0

Created at

2022-09-08 05:16:11 UTC

Updated at

2022-09-08 05:16:11 UTC

NP-MRD ID

NP0262460

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dibenzothiophene

Description

Dibenzothiophene, also known as alpha-thiafluorene or diphenylene sulfide, belongs to the class of organic compounds known as dibenzothiophenes. These are organic heterocyclic compounds with a structure containing a dibenzothiophene moiety, made up of two benzene rings fused to a central thiophene ring. Dibenzothiophene is possibly neutral. dibenzothiophene was first documented in 1999 (PMID: 16232582). A mancude organic heterotricyclic parent that consists of a thiophene ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions (PMID: 15092946) (PMID: 16268154) (PMID: 16391083) (PMID: 17616875).

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       3.610  -1.280   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   30    0
END

View in JSmol

Synonyms

Value	Source
9-Thiafluorene	ChEBI
[1,1'-Biphenyl]-2,2'-diyl sulfide	ChEBI
alpha-Thiafluorene	ChEBI
Diphenylene sulfide	ChEBI
[1,1'-Biphenyl]-2,2'-diyl sulphide	Generator
a-Thiafluorene	Generator
Α-thiafluorene	Generator
Diphenylene sulphide	Generator

Chemical Formula

C₁₂H₈S

Average Mass

184.2600 Da

Monoisotopic Mass

184.03467 Da

IUPAC Name

8-thiatricyclo[7.4.0.0²,⁷]trideca-1(9),2(7),3,5,10,12-hexaene

Traditional Name

dibenzothiophene

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

IYYZUPMFVPLQIF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzothiophenes. These are organic heterocyclic compounds with a structure containing a dibenzothiophene moiety, made up of two benzene rings fused to a central thiophene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiophenes

Sub Class

Dibenzothiophenes

Direct Parent

Dibenzothiophenes

Alternative Parents

Substituents

Dibenzothiophene
1-benzothiophene
Benzenoid
Heteroaromatic compound
Thiophene
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

mancude organic heterotricyclic parent (CHEBI:23681 )
dibenzothiophenes (CHEBI:23681 )
an organosulfur compound (CPD-942 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.38	ALOGPS
logP	3.94	ChemAxon
logS	-4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	55.63 m³·mol⁻¹	ChemAxon
Polarizability	20.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20125

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dibenzothiophene

METLIN ID

Not Available

PubChem Compound

3023

PDB ID

Not Available

ChEBI ID

23681

Good Scents ID

Not Available

References

General References

Yang GP: Polycyclic aromatic hydrocarbons in the sediments of the South China Sea. Environ Pollut. 2000 May;108(2):163-71. doi: 10.1016/s0269-7491(99)00245-6. [PubMed:15092946 ]
Huy NQ, Jin S, Amada K, Haruki M, Huu NB, Hang DT, Ha DT, Imanaka T, Morikawa M, Kanaya S: Characterization of petroleum-degrading bacteria from oil-contaminated sites in Vietnam. J Biosci Bioeng. 1999;88(1):100-2. doi: 10.1016/s1389-1723(99)80184-4. [PubMed:16232582 ]
Wassenberg DM, Nerlinger AL, Battle LP, Di Giulio RT: Effects of the polycyclic aromatic hydrocarbon heterocycles, carbazole and dibenzothiophene, on in vivo and in vitro CYP1A activity and polycyclic aromatic hydrocarbon-derived embryonic deformities. Environ Toxicol Chem. 2005 Oct;24(10):2526-32. doi: 10.1897/04-440r1.1. [PubMed:16268154 ]
Young RF, Cheng SM, Fedorak PM: Aerobic biodegradation of 2,2'-dithiodibenzoic acid produced from dibenzothiophene metabolites. Appl Environ Microbiol. 2006 Jan;72(1):491-6. doi: 10.1128/AEM.72.1.491-496.2006. [PubMed:16391083 ]
Olajire AA, Alade AO, Adeniyi AA, Olabemiwo OM: Distribution of polycyclic aromatic hydrocarbons in surface soils and water from the vicinity of Agbabu bitumen field of Southwestern Nigeria. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2007 Jul;42(8):1043-9. doi: 10.1080/10934520701418474. [PubMed:17616875 ]
LOTUS database [Link]

Showing NP-Card for dibenzothiophene (NP0262460)

MOL for NP0262460 (dibenzothiophene)

3D MOL for NP0262460 (dibenzothiophene)

3D SDF for NP0262460 (dibenzothiophene)

3D-SDF for NP0262460 (dibenzothiophene)

PDB for NP0262460 (dibenzothiophene)

3D PDB for NP0262460 (dibenzothiophene)

SMILES for NP0262460 (dibenzothiophene)

INCHI for NP0262460 (dibenzothiophene)

Structure for NP0262460 (dibenzothiophene)

3D Structure for NP0262460 (dibenzothiophene)