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Showing NP-Card for 4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one (NP0329082)

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Record Information
Version2.0
Created at2022-09-12 13:07:48 UTC
Updated at2022-09-12 13:07:48 UTC
NP-MRD IDNP0329082
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one
DescriptionP-Diazoquinone belongs to the class of organic compounds known as phenoxides. These are salts or analogous metal derivatives of phenols. 4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one is found in Agaricus xanthodermus. 4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one was first documented in 1988 (PMID: 3366422). Based on a literature review a small amount of articles have been published on p-Diazoquinone (PMID: 1521836) (PMID: 1378188) (PMID: 1378176) (PMID: 2067537).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0329082 (4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one)


  Mrv1652309122215072D          

  9  9  0  0  0  0            999 V2000
    0.7145    2.8875    0.0000 N   0  5  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
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3D MOL for NP0329082 (4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one)

     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
    3.4662   -0.7907    0.4325 N   0  0  0  0  0  2  0  0  0  0  0  0
    2.3032   -0.5179    0.0886 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.0804   -0.2366    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788   -1.2966    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331   -1.0153   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6679    0.3657   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8902    0.6685   -0.1619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6686    1.4180   -0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6236    1.1467   -0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -2.3162    0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9421   -1.8428   -0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9712    2.4737   -0.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829    1.9436   -0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9  3  1  0
  4 10  1  0
  5 11  1  0
  8 12  1  0
  9 13  1  0
M  CHG  2   1  -1   2   1
M  END
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3D SDF for NP0329082 (4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one)


  Mrv1652309122215072D          

  9  9  0  0  0  0            999 V2000
    0.7145    2.8875    0.0000 N   0  5  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
NP0329082

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[N-]=[N+]=C1C=CC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H4N2O/c7-8-5-1-3-6(9)4-2-5/h1-4H

> <INCHI_KEY>
WTQZSMDDRMKJRI-UHFFFAOYSA-N

> <FORMULA>
C6H4N2O

> <MOLECULAR_WEIGHT>
120.111

> <EXACT_MASS>
120.032362757

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
10.986770522673044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(-lambda5-diazynylidene)cyclohexa-2,5-dien-1-one

> <JCHEM_LOGP>
-0.4842268208759457

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.069011372113314

> <JCHEM_PKA_STRONGEST_BASIC>
-8.842133884537166

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
33.72879999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-(-lambda5-diazynylidene)cyclohexa-2,5-dien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0329082 (4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one)

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PDB for NP0329082 (4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  N   UNK     0       1.334   5.390   0.000  0.00  0.00           N-1
HETATM    2  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    3                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0329082 (4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one)
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SMILES for NP0329082 (4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one)
[N-]=[N+]=C1C=CC(=O)C=C1
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INCHI for NP0329082 (4-(λ⁵-diazynylidene)cyclohexa-2,5-dien-1-one)
InChI=1S/C6H4N2O/c7-8-5-1-3-6(9)4-2-5/h1-4H
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View in JSmol
Synonyms
ValueSource
4-DiazoquinoneMeSH
Chemical FormulaC6H4N2O
Average Mass120.1110 Da
Monoisotopic Mass120.03236 Da
IUPAC Name4-(-lambda5-diazynylidene)cyclohexa-2,5-dien-1-one
Traditional Name4-(-lambda5-diazynylidene)cyclohexa-2,5-dien-1-one
CAS Registry NumberNot Available
SMILES
[N-]=[N+]=C1C=CC(=O)C=C1
InChI Identifier
InChI=1S/C6H4N2O/c7-8-5-1-3-6(9)4-2-5/h1-4H
InChI KeyWTQZSMDDRMKJRI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agaricus xanthodermusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenoxides. These are salts or analogous metal derivatives of phenols.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassPhenoxides  
Direct ParentPhenoxides  
Alternative Parents
Substituents
  • Phenoxide
    • 

  • Organic diazonium salt
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic salt
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP-0.48ChemAxon
pKa (Strongest Acidic)9.07ChemAxon
pKa (Strongest Basic)-8.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.73 m³·mol⁻¹ChemAxon
Polarizability10.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID71461  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound79130  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kato T, Kikugawa K: Proteins and amino acids as scavengers of nitrite: inhibitory effect on the formation of nitrosodimethylamine and diazoquinone. Food Chem Toxicol. 1992 Jul;30(7):617-26. doi: 10.1016/0278-6915(92)90196-r. [PubMed:1521836  ] 
  2. Kikugawa K, Kato T, Kojima K: Substitution of p- and o-hydroxyphenyl radicals at the 8 position of purine nucleosides by reaction with mutagenic p- and o-diazoquinones. Mutat Res. 1992 Jul;268(1):65-75. doi: 10.1016/0027-5107(92)90084-f. [PubMed:1378188  ] 
  3. Kato T, Kojima K, Hiramoto K, Kikugawa K: DNA strand breakage by hydroxyphenyl radicals generated from mutagenic diazoquinone compounds. Mutat Res. 1992 Jul;268(1):105-14. doi: 10.1016/0027-5107(92)90088-j. [PubMed:1378176  ] 
  4. Kato T, Tadokoro N, Tsutsui M, Kikugawa K: Transformation of arylamines into direct-acting mutagens by reaction with nitrite. Mutat Res. 1991 Jul;249(1):243-54. doi: 10.1016/0027-5107(91)90151-d. [PubMed:2067537  ] 
  5. Kikugawa K, Kato T: Formation of a mutagenic diazoquinone by interaction of phenol with nitrite. Food Chem Toxicol. 1988 Mar;26(3):209-14. doi: 10.1016/0278-6915(88)90121-4. [PubMed:3366422  ] 
  6. LOTUS database [Link]