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Showing NP-Card for coenzyme q0 (NP0314975)

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Record Information
Version2.0
Created at2022-09-11 13:22:15 UTC
Updated at2022-09-11 13:22:15 UTC
NP-MRD IDNP0314975
Secondary Accession NumbersNone
Natural Product Identification
Common Namecoenzyme q0
DescriptionUbiquinone-0, also known as coenzyme Q0 or COQ0, belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6). coenzyme q0 is found in Taiwanofungus camphoratus. coenzyme q0 was first documented in 1998 (PMID: 9413934). Ubiquinone-0 is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 11748217) (PMID: 18830129).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0314975 (coenzyme q0)

Structure #1
  Mrv0541 02241207192D          

 13 13  0  0  0  0            999 V2000
    2.1434   -0.4125    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
    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    1.2375    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
    0.0000    0.8250    0.0000 C   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
    0.7145    2.0625    0.0000 O   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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  2  0  0  0  0
  7  9  1  0  0  0  0
  7 11  2  0  0  0  0
  8  9  2  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
M  END
Download

3D MOL for NP0314975 (coenzyme q0)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
   -2.5367    1.9812    0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5971    1.6246   -0.8086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4311    0.9593   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4717   -0.3570   -0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6238   -1.1061   -0.5518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407   -1.8145    0.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603   -1.0755   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7444   -2.3414    0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0001   -0.3343    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700   -1.0403    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0109    0.9940   -0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7936    1.6886   -0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7977    2.9315   -0.4466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910    1.0602    0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0917    2.6649    0.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638    2.5090   -0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4148   -2.5523    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392   -1.1840    1.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0059   -2.4236    0.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876   -0.4972   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3587   -1.0665    1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2220   -2.1139    0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9623    1.4933    0.1321 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  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  6 17  1  0
  6 18  1  0
  6 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
M  END
Download

3D SDF for NP0314975 (coenzyme q0)

Structure #1
  Mrv0541 02241207192D          

 13 13  0  0  0  0            999 V2000
    2.1434   -0.4125    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
    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    1.2375    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
    0.0000    0.8250    0.0000 C   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
    0.7145    2.0625    0.0000 O   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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  2  0  0  0  0
  7  9  1  0  0  0  0
  7 11  2  0  0  0  0
  8  9  2  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314975

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(=O)C(C)=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c1-5-4-6(10)8(12-2)9(13-3)7(5)11/h4H,1-3H3

> <INCHI_KEY>
UIXPTCZPFCVOQF-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.64196707535999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.6080037166666665

> <ALOGPS_LOGS>
-1.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.717875157092229

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
48.82310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coenzyme Q0

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0314975 (coenzyme q0)

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PDB for NP0314975 (coenzyme q0)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   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   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4    5    6                                                       
CONECT    5    1    4    7                                                  
CONECT    6    4    8   10                                                  
CONECT    7    5    9   11                                                  
CONECT    8    6    9   12                                                  
CONECT    9    7    8   13                                                  
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    2    8                                                       
CONECT   13    3    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0314975 (coenzyme q0)
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SMILES for NP0314975 (coenzyme q0)
COC1=C(OC)C(=O)C(C)=CC1=O
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INCHI for NP0314975 (coenzyme q0)
InChI=1S/C9H10O4/c1-5-4-6(10)8(12-2)9(13-3)7(5)11/h4H,1-3H3
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View in JSmol
Synonyms
ValueSource
2,3-Dimethoxy-5-methyl-1,4-benzoquinoneChEBI
2,3-Dimethoxy-5-methyl-p-benzoquinoneChEBI
2,3-Dimethoxy-5-methylbenzo-1,4-quinoneChEBI
2,3-Dimethoxy-5-methylbenzoquinoneChEBI
2-Methyl-4,5-dimethoxy-p-quinoneChEBI
2-Methyl-5,6-dimethoxybenzoquinoneChEBI
Coenzyme Q0ChEBI
CoQ0ChEBI
Q0ChEBI
Ubiquinone 0ChEBI
Coenzyme qoMeSH
2,3-Dimethoxy-5-methyl-2,5-cyclohexadiene-1,4-dioneMeSH
CCRIS 7153MeSH
UQ(0) CPDMeSH
Ubiquinone-OMeSH
Chemical FormulaC9H10O4
Average Mass182.1733 Da
Monoisotopic Mass182.05791 Da
IUPAC Name2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione
Traditional Namecoenzyme Q0
CAS Registry NumberNot Available
SMILES
COC1=C(OC)C(=O)C(C)=CC1=O
InChI Identifier
InChI=1S/C9H10O4/c1-5-4-6(10)8(12-2)9(13-3)7(5)11/h4H,1-3H3
InChI KeyUIXPTCZPFCVOQF-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
Taiwanofungus camphoratusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassQuinone and hydroquinone lipids  
Direct ParentUbiquinones  
Alternative Parents
Substituents
  • Ubiquinone skeleton
    • 

  • Quinone
    • 

  • P-benzoquinone
    • 

  • Vinylogous ester
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP0.53ALOGPS
logP0.61ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.82 m³·mol⁻¹ChemAxon
Polarizability17.64 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD0-1464  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound69068  
PDB IDNot Available
ChEBI ID27906  
Good Scents IDNot Available
References
General References
  1. Guo Q, Corbett JT, Yue G, Fann YC, Qian SY, Tomer KB, Mason RP: Electron spin resonance investigation of semiquinone radicals formed from the reaction of ubiquinone 0 with human oxyhemoglobin. J Biol Chem. 2002 Feb 22;277(8):6104-10. doi: 10.1074/jbc.M106395200. Epub 2001 Dec 17. [PubMed:11748217  ] 
  2. Somers-Edgar TJ, Rosengren RJ: Coenzyme Q0 induces apoptosis and modulates the cell cycle in estrogen receptor negative breast cancer cells. Anticancer Drugs. 2009 Jan;20(1):33-40. doi: 10.1097/CAD.0b013e328314b5c5. [PubMed:18830129  ] 
  3. Roginsky VA, Bruchelt G, Bartuli O: Ubiquinone-0 (2,3-dimethoxy-5-methyl-1,4-benzoquinone) as effective catalyzer of ascorbate and epinephrine oxidation and damager of neuroblastoma cells. Biochem Pharmacol. 1998 Jan 1;55(1):85-91. doi: 10.1016/s0006-2952(97)00434-6. [PubMed:9413934  ] 
  4. LOTUS database [Link]