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Showing NP-Card for Dopamine quinone (NP0091982)

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Record Information
Version2.0
Created at2022-05-11 18:53:51 UTC
Updated at2022-05-11 18:53:51 UTC
NP-MRD IDNP0091982
Secondary Accession NumbersNone
Natural Product Identification
Common NameDopamine quinone
DescriptionDopamine quinone, also known as DoQ, belongs to the class of organic compounds known as o-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 2-positions, respectively. Dopamine quinone is a very strong basic compound (based on its pKa). Dopamine quinone is found in Daphnia pulex. Dopamine quinone was first documented in 2004 (PMID: 14985818). If this occurs within the neuronal cytosol, the quinone may react with cytosolic components, particularly with cysteine residues.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0091982 (Dopamine quinone)


  Mrv0541 02241203502D          

 11 11  0  0  0  0            999 V2000
   14.1971   -8.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7846   -9.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1971   -6.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0221   -6.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9596   -7.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7846   -7.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9596   -9.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5471   -8.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4346   -6.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5471   -9.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7221   -8.3845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  2  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5  8  1  0  0  0  0
  5  6  2  0  0  0  0
  7 10  2  0  0  0  0
  7  8  1  0  0  0  0
  8 11  2  0  0  0  0
M  END
Download

3D MOL for NP0091982 (Dopamine quinone)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.2793   -0.6542   -1.0419 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359   -0.6022    0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545    0.4004    0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1306    0.1959    0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5785   -0.8038   -0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9781   -0.9446   -0.6682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4258   -1.8871   -1.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9406    0.0701   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1597    0.0206   -0.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3933    1.1553    0.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    1.1907    0.8744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2230   -1.0232   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503    0.3663   -1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2538   -0.2456    0.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1312   -1.6074    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5774    1.4003    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716    0.5142    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1202   -1.5373   -0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837    1.9375    0.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7977    2.0541    1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
  8 10  1  0
 10 11  2  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  5 18  1  0
 10 19  1  0
 11 20  1  0
M  END
Download

3D SDF for NP0091982 (Dopamine quinone)


  Mrv0541 02241203502D          

 11 11  0  0  0  0            999 V2000
   14.1971   -8.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7846   -9.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1971   -6.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0221   -6.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9596   -7.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7846   -7.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9596   -9.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5471   -8.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4346   -6.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5471   -9.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7221   -8.3845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  2  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5  8  1  0  0  0  0
  5  6  2  0  0  0  0
  7 10  2  0  0  0  0
  7  8  1  0  0  0  0
  8 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0091982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCC1=CC(=O)C(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H9NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5H,3-4,9H2

> <INCHI_KEY>
PQPXZWUZIOASKS-UHFFFAOYSA-N

> <FORMULA>
C8H9NO2

> <MOLECULAR_WEIGHT>
151.1626

> <EXACT_MASS>
151.063328537

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
15.251665329224352

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(2-aminoethyl)cyclohexa-3,5-diene-1,2-dione

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
0.47286177

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.75526652401606

> <JCHEM_POLAR_SURFACE_AREA>
60.160000000000004

> <JCHEM_REFRACTIVITY>
43.6482

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(2-aminoethyl)cyclohexa-3,5-diene-1,2-dione

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0091982 (Dopamine quinone)

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PDB for NP0091982 (Dopamine quinone)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      26.501 -15.651   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.731 -16.985   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.501 -12.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.041 -12.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.191 -14.317   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.731 -14.317   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.191 -16.985   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.421 -15.651   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      28.811 -11.650   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      23.421 -18.318   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      21.881 -15.651   0.000  0.00  0.00           O+0
CONECT    1    6    2                                                       
CONECT    2    1    7                                                       
CONECT    3    4    6                                                       
CONECT    4    3    9                                                       
CONECT    5    8    6                                                       
CONECT    6    1    3    5                                                  
CONECT    7    2   10    8                                                  
CONECT    8    5    7   11                                                  
CONECT    9    4                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0091982 (Dopamine quinone)
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SMILES for NP0091982 (Dopamine quinone)
NCCC1=CC(=O)C(=O)C=C1
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INCHI for NP0091982 (Dopamine quinone)
InChI=1S/C8H9NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5H,3-4,9H2
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View in JSmol
Synonyms
ValueSource
4-(2-Aminoethyl)-1,2-benzoquinoneChEBI
4-(2-Aminoethyl)-O-benzoquinoneChEBI
Dopamine O-quinoneChEBI
DoQChEBI
4-(2-Aminoethyl)-3,5-cyclohexadiene-1,2-dioneHMDB
DopaminoquinoneHMDB
Dopamine quinoneChEBI
Chemical FormulaC8H9NO2
Average Mass151.1626 Da
Monoisotopic Mass151.06333 Da
IUPAC Name4-(2-aminoethyl)cyclohexa-3,5-diene-1,2-dione
Traditional Name4-(2-aminoethyl)cyclohexa-3,5-diene-1,2-dione
CAS Registry NumberNot Available
SMILES
NCCC1=CC(=O)C(=O)C=C1
InChI Identifier
InChI=1S/C8H9NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5H,3-4,9H2
InChI KeyPQPXZWUZIOASKS-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
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Daphnia pulexLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 2-positions, respectively.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentO-benzoquinones  
Alternative Parents
Substituents
  • O-benzoquinone
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Amine
    • 

  • 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
logP-0.29ALOGPS
logP0.47ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.16 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.65 m³·mol⁻¹ChemAxon
Polarizability15.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012219  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028863  
KNApSAcK IDNot Available
Chemspider ID142759  
KEGG Compound IDC17755  
BioCyc IDCPD-8851  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162602  
PDB IDNot Available
ChEBI ID74684  
Good Scents IDNot Available
References
General References
  1. Jameson GN, Zhang J, Jameson RF, Linert W: Kinetic evidence that cysteine reacts with dopaminoquinone via reversible adduct formation to yield 5-cysteinyl-dopamine: an important precursor of neuromelanin. Org Biomol Chem. 2004 Mar 7;2(5):777-82. doi: 10.1039/b316294j. Epub 2004 Feb 11. [PubMed:14985818  ]