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Showing NP-Card for 2,6-Dimethoxy-1,4-benzoquinone (NP0045444)

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Record Information
Version2.0
Created at2022-03-17 19:20:04 UTC
Updated at2022-03-17 19:20:04 UTC
NP-MRD IDNP0045444
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,6-Dimethoxy-1,4-benzoquinone
Description2,6-Dimethoxy-1,4-benzoquinone, also known as 2, 6-dimethoxyquinone or 2,6-dimethoxysemiquinone radicals, belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. 2,6-Dimethoxy-1,4-benzoquinone is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,6-Dimethoxybenzoquinone (2,6-DMBQ) is a benzoquinone, a chemical compound found in Rauvolfia vomitoria and in Tibouchina pulchra. Outside of the human body, 2,6-Dimethoxy-1,4-benzoquinone has been detected, but not quantified in, common wheats and green vegetables. This could make 2,6-dimethoxy-1,4-benzoquinone a potential biomarker for the consumption of these foods. At physiological concentrations 2,6-Dimethoxy-p-benzoquinone is an antibacterial substance, in non-physiological, highly elevated concentrations might be mutagenic, cytotoxic, genotoxic, and hepatotoxic. 2,6-Dimethoxy-1,4-benzoquinone is found in Acacia melanoxylon R.Br. , Adonis vernalis , Ailanthus integrifolia, Alnus japonica, Annona cherimola, Artemisia capillaris, Atractylodes macrocephala, Baccharis megapotamica, Berchemia racemosa, Brucea javanica, Bruguiera rhynchopetala, Caesalpinia pulcherrima , Pisonia umbellifera, Chrysanthemum leucanthemum, Cinnamomum kotoense, Diospyros eriantha, Durio kutejensis , Eleutherococcus senticosus, Engelhardia roxburghiana, Enkianthus nudipes, Eucalyptus globulus, Euterpe oleracea, Fagara tessmannii Engl., Fraxinus chinensis, Helianthus heterophyllus, Hydrangea macrophylla, Iris milesii, Kielmeyera rupestris, Licaria triandra, Lindera glauca, Liriodendron tulipifera, Macaranga tanarius, Marsdenia tinctoria, Melicope semecarpifolia, Neolitsea acuminatissima, Pentaclethra eetveldeana, Phyllostachys heterocycla var.pubescens, Plumeria rubra, Populus pseudosimonii, Rauvolfia vomitoria , Rhizophora apiculata, Senecio vulgaris, Senna alata, Striga asiatica , Strobilanthes formosanus, Tapeinidium pinnatum, Toddalia asiatica , Triumfetta rhomboidea, Ulmus thomasii, Verbesina virginica, Viscum coloratum , Zanthoxylum beecheyanum, Zanthoxylum gilletii and Zanthoxylum nitidum. , But some scientists challenge its mutagenicity and others totally exclude such a possibility.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045444 (2,6-Dimethoxy-1,4-benzoquinone)

2,6-Dimethoxybenzoquinone
  Mrv1652309241723442D          

 12 12  0  0  0  0            999 V2000
    5.2224    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 12  1  0  0  0  0
  2  6  1  0  0  0  0
  2 11  1  0  0  0  0
  3  7  2  0  0  0  0
  4 10  2  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for NP0045444 (2,6-Dimethoxy-1,4-benzoquinone)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
    3.5548    0.0412    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5410    0.9892   -0.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2363    0.5396   -0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134    0.2687   -1.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4445   -0.1929   -1.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7670   -0.4584   -3.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186   -0.3527   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1021   -0.0820    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0183   -0.2281    1.4991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2686    0.4395    1.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    0.3779    0.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5973    0.6441    1.8771 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5057    0.5589    0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7208   -0.5550   -0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2683   -0.6104    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    0.3902   -2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180   -0.6960   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7879    0.1429    2.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1482    1.5456    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8676    0.1323    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  7 17  1  0
 10 18  1  0
 10 19  1  0
 10 20  1  0
M  END
Download

3D SDF for NP0045444 (2,6-Dimethoxy-1,4-benzoquinone)

2,6-Dimethoxybenzoquinone
  Mrv1652309241723442D          

 12 12  0  0  0  0            999 V2000
    5.2224    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 12  1  0  0  0  0
  2  6  1  0  0  0  0
  2 11  1  0  0  0  0
  3  7  2  0  0  0  0
  4 10  2  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C=C(OC)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3

> <INCHI_KEY>
OLBNOBQOQZRLMP-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.541331430203844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dimethoxycyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
0.36

> <JCHEM_LOGP>
0.21245322733333313

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6529514732610515

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
44.46600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dimethoxy-1,4-benzoquinone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0045444 (2,6-Dimethoxy-1,4-benzoquinone)

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PDB for NP0045444 (2,6-Dimethoxy-1,4-benzoquinone)
HEADER    PROTEIN                                 24-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2,6-Dimethoxybenzoquinone                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-SEP-17         0                                  
HETATM    1  O   UNK     0       9.748   1.540   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.414   1.540   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081   3.080   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.081  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.415   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082   0.770   0.000  0.00  0.00           C+0
CONECT    1    5   12                                                       
CONECT    2    6   11                                                       
CONECT    3    7                                                            
CONECT    4   10                                                            
CONECT    5    1    7    9                                                  
CONECT    6    2    7    8                                                  
CONECT    7    3    5    6                                                  
CONECT    8    6   10                                                       
CONECT    9    5   10                                                       
CONECT   10    4    8    9                                                  
CONECT   11    2                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0045444 (2,6-Dimethoxy-1,4-benzoquinone)
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SMILES for NP0045444 (2,6-Dimethoxy-1,4-benzoquinone)
COC1=CC(=O)C=C(OC)C1=O
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INCHI for NP0045444 (2,6-Dimethoxy-1,4-benzoquinone)
InChI=1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3
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Synonyms
ValueSource
2,6-Dimetoxy-p-benzoquinoneKegg
2, 6-Dimethoxy-1,4-benzoquinoneHMDB
2, 6-Dimethoxy-p-benzoquinoneHMDB
2, 6-DimethoxyquinoneHMDB
2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy- (9ci)HMDB
2,6-Dimethoxy-2,5-cyclohexadiene-1,4-dioneHMDB
2,6-Dimethoxy-p-benzoquinoneHMDB
2,6-Dimethoxy-p-quinoneHMDB
2,6-Dimethoxybenzo-1,4-quinoneHMDB
2,6-DimethoxybenzoquinoneHMDB
2,6-DimethoxyquinoneHMDB
2,6-Dimethoxysemiquinone anionsHMDB
2,6-Dimethoxysemiquinone radicalsHMDB
DMBQHMDB
Ghl.PD_Mitscher_leg0.4HMDB
2,6-Dimethoxy-1,4-benzoquinoneMeSH
Chemical FormulaC8H8O4
Average Mass168.1467 Da
Monoisotopic Mass168.04226 Da
IUPAC Name2,6-dimethoxycyclohexa-2,5-diene-1,4-dione
Traditional Name2,6-dimethoxy-1,4-benzoquinone
CAS Registry Number530-55-2
SMILES
COC1=CC(=O)C=C(OC)C1=O
InChI Identifier
InChI=1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3
InChI KeyOLBNOBQOQZRLMP-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acacia melanoxylonPlant
Adonis vernalisPlant
Ailanthus integrifoliaLOTUS Database
Alnus japonicaLOTUS Database
Annona cherimolaLOTUS Database
Artemisia capillarisLOTUS Database
Atractylodes macrocephalaLOTUS Database
Baccharis megapotamicaLOTUS Database
Berchemia racemosaLOTUS Database
Brucea javanicaLOTUS Database
Bruguiera x rhynchopetalaLOTUS Database
Caesalpinia pulcherrimaPlant
Ceodes umbelliferaLOTUS Database
Chrysanthemum leucanthemumPlant
Cinnamomum kotoenseLOTUS Database
Diospyros erianthaPlant
Durio kutejensisPlant
Eleutherococcus senticosusLOTUS Database
Engelhardia roxburghianaPlant
Enkianthus nudipesLOTUS Database
Eucalyptus globulusLOTUS Database
Euterpe oleraceaLOTUS Database
Fagara tessmannii Engl.Plant
Fraxinus chinensisLOTUS Database
Helianthus heterophyllusPlant
Hydrangea macrophyllaLOTUS Database
Iris milesiiLOTUS Database
Kielmeyera rupestrisLOTUS Database
Licaria triandraLOTUS Database
Lindera glaucaLOTUS Database
Liriodendron tulipiferaLOTUS Database
Macaranga tanariusLOTUS Database
Marsdenia tinctoriaLOTUS Database
Melicope semecarpifoliaLOTUS Database
Neolitsea acuminatissimaPlant
Pentaclethra eetveldeanaLOTUS Database
Phyllostachys heterocycla var.pubescensPlant
Plumeria rubraLOTUS Database
Populus pseudosimoniiPlant
Rauvolfia vomitoriaPlant
Rhizophora apiculataLOTUS Database
Senecio vulgarisLOTUS Database
Senna alataLOTUS Database
Striga asiaticaPlant
Strobilanthes formosanusPlant
Tapeinidium pinnatumLOTUS Database
Toddalia asiaticaPlant
Triticum aestivumFooDB
Triumfetta rhomboideaLOTUS Database
Ulmus thomasiiLOTUS Database
Verbesina virginicaLOTUS Database
Viscum coloratumPlant
Zanthoxylum beecheyanumLOTUS Database
Zanthoxylum gilletiiLOTUS Database
Zanthoxylum nitidumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentP-benzoquinones  
Alternative Parents
Substituents
  • P-benzoquinone
    • 

  • Vinylogous ester
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP0.36ALOGPS
logP0.21ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.47 m³·mol⁻¹ChemAxon
Polarizability15.54 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029673  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000858  
KNApSAcK IDC00000258  
Chemspider ID61560  
KEGG Compound IDC10331  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,6-Dimethoxybenzoquinone  
METLIN IDNot Available
PubChem Compound68262  
PDB IDKIA  
ChEBI ID544013  
Good Scents IDNot Available
References
General ReferencesNot Available