Np mrd loader

Showing NP-Card for diphenyleneiodonium (NP0315960)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-11 14:51:11 UTC
Updated at2022-09-11 14:51:11 UTC
NP-MRD IDNP0315960
Secondary Accession NumbersNone
Natural Product Identification
Common Namediphenyleneiodonium
DescriptionDibenziodolium belongs to the class of organic compounds known as aryl iodides. These are organic compounds containing the acyl iodide functional group. diphenyleneiodonium is found in Ixora coccinea. diphenyleneiodonium was first documented in 2015 (PMID: 25951091). Based on a literature review a small amount of articles have been published on dibenziodolium (PMID: 35858372) (PMID: 35176856) (PMID: 35424399) (PMID: 31415760).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0315960 (diphenyleneiodonium)


  Mrv1652309112216512D          

 13 15  0  0  0  0            999 V2000
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 I   0  3  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  4 13  1  0  0  0  0
M  CHG  1   7   1
M  END
Download

3D MOL for NP0315960 (diphenyleneiodonium)

Download
3D SDF for NP0315960 (diphenyleneiodonium)

  Mrv1652309112216512D          

 13 15  0  0  0  0            999 V2000
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 I   0  3  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  4 13  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0315960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[I+]1C2=CC=CC=C2C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H8I/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H/q+1

> <INCHI_KEY>
QFXKXRXFBRLLPQ-UHFFFAOYSA-N

> <FORMULA>
C12H8I

> <MOLECULAR_WEIGHT>
279.1

> <EXACT_MASS>
278.96652

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
22.84883216761517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8lambda3-iodatricyclo[7.4.0.0^{2,7}]trideca-1(13),2,4,6,9,11-hexaen-8-ylium

> <JCHEM_LOGP>
4.237384875

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
63.97300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8lambda3-iodatricyclo[7.4.0.0^{2,7}]trideca-1(13),2,4,6,9,11-hexaen-8-ylium

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0315960 (diphenyleneiodonium)
Download
PDB for NP0315960 (diphenyleneiodonium)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         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  I   UNK     0       3.610  -1.280   0.000  0.00  0.00           I+1
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    8    4                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   30    0
END

Download
3D PDB for NP0315960 (diphenyleneiodonium)
Download
SMILES for NP0315960 (diphenyleneiodonium)
[I+]1C2=CC=CC=C2C2=CC=CC=C12
Download
INCHI for NP0315960 (diphenyleneiodonium)
InChI=1S/C12H8I/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H/q+1
Download
View in JSmol
Synonyms
ValueSource
(1,1'-Biphenyl)-2,2'-diyliodoniumChEBI
2,2'-BiphenylyleneiodoniumChEBI
DiphenyleneiodoniumChEBI
Diphenyleneiodium chlorideMeSH
Diphenyleneiodonium chlorideMeSH
Diphenyleneiodonium, 131I-labeledMeSH
Diphenylene iodoniumMeSH
Diphenyleneiodonium sulfate (2:1)MeSH
Diphenyleneiodonium sulfate (2:1), 125I-labeledMeSH
Chemical FormulaC12H8I
Average Mass279.1000 Da
Monoisotopic Mass278.96652 Da
IUPAC Name8lambda3-iodatricyclo[7.4.0.0^{2,7}]trideca-1(13),2,4,6,9,11-hexaen-8-ylium
Traditional Name8lambda3-iodatricyclo[7.4.0.0^{2,7}]trideca-1(13),2,4,6,9,11-hexaen-8-ylium
CAS Registry NumberNot Available
SMILES
[I+]1C2=CC=CC=C2C2=CC=CC=C12
InChI Identifier
InChI=1S/C12H8I/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H/q+1
InChI KeyQFXKXRXFBRLLPQ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ixora coccineaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl iodides. These are organic compounds containing the acyl iodide functional group.
KingdomOrganic compounds  
Super ClassOrganohalogen compounds  
ClassAryl halides  
Sub ClassAryl iodides  
Direct ParentAryl iodides  
Alternative Parents
Substituents
  • Benzenoid
    • 

  • Aryl iodide
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic cation
    • 

  • 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
logP4.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity63.97 m³·mol⁻¹ChemAxon
Polarizability22.85 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2990  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3101  
PDB IDNot Available
ChEBI ID77986  
Good Scents IDNot Available
References
General References
  1. Il'in MV, Novikov AS, Bolotin DS: Sulfonium and Selenonium Salts as Noncovalent Organocatalysts for the Multicomponent Groebke-Blackburn-Bienayme Reaction. J Org Chem. 2022 Aug 5;87(15):10199-10207. doi: 10.1021/acs.joc.2c01141. Epub  2022 Jul 20. [PubMed:35858372  ] 
  2. Il'in MV, Sysoeva AA, Novikov AS, Bolotin DS: Diaryliodoniums as Hybrid Hydrogen- and Halogen-Bond-Donating Organocatalysts for the Groebke-Blackburn-Bienayme Reaction. J Org Chem. 2022 Apr 1;87(7):4569-4579. doi: 10.1021/acs.joc.1c02885. Epub 2022  Feb 17. [PubMed:35176856  ] 
  3. Yunusova SN, Novikov AS, Soldatova NS, Vovk MA, Bolotin DS: Iodonium salts as efficient iodine(iii)-based noncovalent organocatalysts for Knorr-type reactions. RSC Adv. 2021 Jan 22;11(8):4574-4583. doi: 10.1039/d0ra09640g. eCollection 2021  Jan 21. [PubMed:35424399  ] 
  4. Wang Y, Wang XJ, Zhao LM, Pang ZD, She G, Song Z, Cheng X, Du XJ, Deng XL: Oxidative stress induced by palmitic acid modulates K(Ca)2.3 channels in vascular endothelium. Exp Cell Res. 2019 Oct 15;383(2):111552. doi: 10.1016/j.yexcr.2019.111552. Epub  2019 Aug 12. [PubMed:31415760  ] 
  5. Postnikov PS, Guselnikova OA, Yusubov MS, Yoshimura A, Nemykin VN, Zhdankin VV: Preparation and X-ray Structural Study of Dibenziodolium Derivatives. J Org Chem. 2015 Jun 5;80(11):5783-8. doi: 10.1021/acs.joc.5b00741. Epub 2015 May  15. [PubMed:25951091  ] 
  6. LOTUS database [Link]