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Showing NP-Card for Dibenzofuran (NP0002787)

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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
Provided ByBMRBBMRB logo
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. Dibenzofuran is found in Angelica gigas and Artemisia monosperma. It was first documented in 2002 (PMID: 12009135). Based on a literature review a small amount of articles have been published on Dibenzofuran (PMID: 17984079) (PMID: 20686914) (PMID: 21554085) (PMID: 34299565) (PMID: 34369666) (PMID: 34323721).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002787 (Dibenzofuran)


  Mrv1652304272019032D          

 13 15  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5457    2.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994    2.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    2.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    1.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9645    1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6320    0.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  5  1  0  0  0  0
  2  4  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  6 10  2  0  0  0  0
  7 11  2  0  0  0  0
  8 12  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for NP0002787 (Dibenzofuran)

NP0002787
     RDKit          3D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -3.3841    0.4282   -0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -0.8798   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6756   -1.2264    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -0.2542   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0512    1.0694   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968    1.3855   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0619    1.7451   -0.2163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151    0.9851   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610    1.2711    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3775    0.2638    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9255   -1.0287    0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5864   -1.3354    0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6827   -0.3156    0.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4268    0.7314   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7510   -1.6521   -0.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -2.2408    0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6659    2.4175   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037    2.2973   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4303    0.4965    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608   -1.7999    0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702   -2.3578    0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6  1  1  0
 13  8  1  0
 13  4  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  6 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
M  END
Download

3D SDF for NP0002787 (Dibenzofuran)


  Mrv1652304272019032D          

 13 15  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5457    2.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994    2.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    2.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    1.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9645    1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6320    0.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  5  1  0  0  0  0
  2  4  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  6 10  2  0  0  0  0
  7 11  2  0  0  0  0
  8 12  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0002787

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
TXCDCPKCNAJMEE-UHFFFAOYSA-N

> <FORMULA>
C12H8O

> <MOLECULAR_WEIGHT>
168.1913

> <EXACT_MASS>
168.057514878

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
18.354862981127845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(13),2,4,6,9,11-hexaene

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
3.1512470969999997

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9631584571676832

> <JCHEM_POLAR_SURFACE_AREA>
13.14

> <JCHEM_REFRACTIVITY>
51.22680000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(13),2,4,6,9,11-hexaene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002787 (Dibenzofuran)

NP0002787
     RDKit          3D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -3.3841    0.4282   -0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -0.8798   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6756   -1.2264    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -0.2542   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0512    1.0694   -0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968    1.3855   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0619    1.7451   -0.2163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151    0.9851   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610    1.2711    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3775    0.2638    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9255   -1.0287    0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5864   -1.3354    0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6827   -0.3156    0.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4268    0.7314   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7510   -1.6521   -0.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -2.2408    0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6659    2.4175   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037    2.2973   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4303    0.4965    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608   -1.7999    0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702   -2.3578    0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6  1  1  0
 13  8  1  0
 13  4  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  6 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
M  END
Download

PDB for NP0002787 (Dibenzofuran)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.885   4.915   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.292   4.289   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.640   4.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.453   2.757   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.800   2.478   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.207   1.852   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.046   0.320   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    1    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   10   11                                                  
CONECT   10    6    9   12                                                  
CONECT   11    7    9   13                                                  
CONECT   12    8   10   13                                                  
CONECT   13   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   30    0
END
Download

3D PDB for NP0002787 (Dibenzofuran)

COMPND    NP0002787
HETATM    1  C1  UNL     1      -3.384   0.428  -0.302  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.003  -0.880  -0.108  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.676  -1.226   0.033  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.684  -0.254  -0.018  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.051   1.069  -0.212  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.397   1.386  -0.351  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.062   1.745  -0.216  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.115   0.985  -0.043  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.461   1.271   0.019  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.377   0.264   0.214  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.926  -1.029   0.344  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.586  -1.335   0.285  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.683  -0.316   0.090  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.427   0.731  -0.416  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.751  -1.652  -0.065  1.00  0.00           H  
HETATM   16  H3  UNL     1      -1.337  -2.241   0.186  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.666   2.418  -0.501  1.00  0.00           H  
HETATM   18  H5  UNL     1       2.804   2.297  -0.086  1.00  0.00           H  
HETATM   19  H6  UNL     1       4.430   0.497   0.261  1.00  0.00           H  
HETATM   20  H7  UNL     1       3.661  -1.800   0.495  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.270  -2.358   0.391  1.00  0.00           H  
CONECT    1    2    2    6   14
CONECT    2    3   15
CONECT    3    4    4   16
CONECT    4    5   13
CONECT    5    6    6    7
CONECT    6   17
CONECT    7    8
CONECT    8    9    9   13
CONECT    9   10   18
CONECT   10   11   11   19
CONECT   11   12   20
CONECT   12   13   13   21
END
Download

SMILES for NP0002787 (Dibenzofuran)

O1C2=CC=CC=C2C2=CC=CC=C12
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INCHI for NP0002787 (Dibenzofuran)

InChI=1S/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H
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View in JSmol
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Angelica gigasLOTUS Database
Artemisia monospermaLOTUS Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
HMDB IDHMDB0251164
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 Compound568
PDB IDNot Available
ChEBI ID28145
Good Scents IDNot Available
References
General References
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