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Record Information
Version1.0
Created at2020-11-23 19:40:26 UTC
Updated at2021-08-12 19:52:09 UTC
NP-MRD IDNP0002787
Secondary Accession NumbersNone
Natural Product Identification
Common NameDibenzofuran
DescriptionDibenzofuran, also known as diphenylene oxide or DBF, belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring. Dibenzofuran is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2002 (PMID: 12009135). Based on a literature review a significant number of articles have been published on dibenzofuran (PMID: 17984079) (PMID: 20686914) (PMID: 21554085) (PMID: 34323721).
Structure
Thumb
Synonyms
ValueSource
DBFChEBI
Diphenylene oxideChEBI
Chemical FormulaC12H8O
Average Mass168.1913 Da
Monoisotopic Mass168.05751 Da
IUPAC Name8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(13),2,4,6,9,11-hexaene
Traditional Name8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(13),2,4,6,9,11-hexaene
CAS Registry NumberNot Available
SMILES
O1C2=CC=CC=C2C2=CC=CC=C12
InChI Identifier
InChI=1S/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H
InChI KeyTXCDCPKCNAJMEE-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Crataegus monogynaKNApSAcK Database
Crataegus ponticaKNApSAcK Database
Pyrus communisKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassDibenzofurans
Direct ParentDibenzofurans
Alternative Parents
Substituents
  • Dibenzofuran
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.92ALOGPS
logP3.15ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.23 m³·mol⁻¹ChemAxon
Polarizability18.35 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002396
Chemspider ID551
KEGG Compound IDC07729
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDibenzofuran
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28145
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Romer MC, Hammer E, Cazau MC, Arambarri AM: Isolation and characterization of biarylic structure-degrading yeasts: hydroxylation potential of dibenzofuran. Environ Pollut. 2002;118(3):379-82. doi: 10.1016/s0269-7491(01)00290-1. [PubMed:12009135 ]
  3. Jaiswal PK, Kohli S, Gopal M, Thakur IS: Isolation and characterization of alkalotolerant Pseudomonas sp. strain ISTDF1 for degradation of dibenzofuran. J Ind Microbiol Biotechnol. 2011 Apr;38(4):503-11. doi: 10.1007/s10295-010-0793-7. Epub 2010 Aug 5. [PubMed:20686914 ]
  4. Duarte FV, Simoes AM, Teodoro JS, Rolo AP, Palmeira CM: Exposure to dibenzofuran affects lung mitochondrial function in vitro. Toxicol Mech Methods. 2011 Oct;21(8):571-6. doi: 10.3109/15376516.2011.576714. Epub 2011 May 9. [PubMed:21554085 ]
  5. Zhang L, Qiu X, Huang L, Xu J, Wang W, Li Z, Xu P, Tang H: Microbial degradation of multiple PAHs by a microbial consortium and its application on contaminated wastewater. J Hazard Mater. 2021 Jun 28;419:126524. doi: 10.1016/j.jhazmat.2021.126524. [PubMed:34323721 ]