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Showing NP-Card for hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione (NP0320429)

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Record Information
Version2.0
Created at2022-09-11 22:04:20 UTC
Updated at2022-09-11 22:04:20 UTC
NP-MRD IDNP0320429
Secondary Accession NumbersNone
Natural Product Identification
Common Namehexahydroxy-[5,5'-bipyrimidine]-2,2'-dione
DescriptionALLOXANTIN, also known as uroxin, belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups. hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione is found in Corbicula japonica. Based on a literature review very few articles have been published on ALLOXANTIN.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0320429 (hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione)


  Mrv1652309122200042D          

 20 21  0  0  0  0            999 V2000
    0.1842   -3.5195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.2820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -0.4125    0.0000 O   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
    1.2448   -1.0445    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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 N   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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  2 20  1  0  0  0  0
M  END
Download

3D MOL for NP0320429 (hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
    4.2155    0.3247   -1.5507 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1344    0.3350   -0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264   -0.6094    0.0553 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938   -0.6180    0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6185   -1.6373    1.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6331    0.2949    0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1100    1.0760    1.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5615   -0.5557   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0190   -1.6556   -0.7662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3598   -1.0220    1.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7863   -1.7644    2.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250   -0.8016    1.1030 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3769   -0.1044    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6104    0.1055    0.2263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6022    0.3417   -0.9693 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620    0.1488   -1.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6462    0.5899   -2.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9833    1.2937   -0.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0742    2.3113   -0.9610 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0951    1.2862   -1.2087 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3041   -1.6747    2.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7031    1.8605    1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6682   -2.1818   -1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880   -1.4579    3.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0881    0.9109   -3.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3639    3.2035   -1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 20  1  0
 20 18  2  0
 18 19  1  0
 18  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
  6  4  1  0
 16  8  1  0
  5 21  1  0
 19 26  1  0
  7 22  1  0
  9 23  1  0
 11 24  1  0
 17 25  1  0
M  END
Download

3D SDF for NP0320429 (hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione)


  Mrv1652309122200042D          

 20 21  0  0  0  0            999 V2000
    0.1842   -3.5195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.2820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -0.4125    0.0000 O   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
    1.2448   -1.0445    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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 N   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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320429

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=NC(=O)N=C(O)C1(O)C1(O)C(O)=NC(=O)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H6N4O8/c13-1-7(19,2(14)10-5(17)9-1)8(20)3(15)11-6(18)12-4(8)16/h19-20H,(H2,9,10,13,14,17)(H2,11,12,15,16,18)

> <INCHI_KEY>
IWDDXZKCDHOOSF-UHFFFAOYSA-N

> <FORMULA>
C8H6N4O8

> <MOLECULAR_WEIGHT>
286.156

> <EXACT_MASS>
286.018563169

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.11971980692779

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexahydroxy-2H,2'H,5H,5'H-[5,5'-bipyrimidine]-2,2'-dione

> <JCHEM_LOGP>
-2.522008964666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
-1.3407300966824467

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.0638013076574078

> <JCHEM_PKA_STRONGEST_BASIC>
-5.055068601765153

> <JCHEM_POLAR_SURFACE_AREA>
204.95999999999998

> <JCHEM_REFRACTIVITY>
53.873200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0320429 (hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione)

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PDB for NP0320429 (hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione)
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  O   UNK     0       0.344  -6.570   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.344  -5.030   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.990  -4.260   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.990  -2.720   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.324  -1.950   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.344  -1.950   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.646  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.324  -1.950   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.677  -2.720   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.011  -1.950   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       1.677  -4.260   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   18                                             
CONECT    7    6                                                            
CONECT    8    6    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16                                                            
CONECT   18    6   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

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3D PDB for NP0320429 (hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione)
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SMILES for NP0320429 (hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione)
OC1=NC(=O)N=C(O)C1(O)C1(O)C(O)=NC(=O)N=C1O
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INCHI for NP0320429 (hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione)
InChI=1S/C8H6N4O8/c13-1-7(19,2(14)10-5(17)9-1)8(20)3(15)11-6(18)12-4(8)16/h19-20H,(H2,9,10,13,14,17)(H2,11,12,15,16,18)
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Synonyms
ValueSource
UroxinMeSH
Chemical FormulaC8H6N4O8
Average Mass286.1560 Da
Monoisotopic Mass286.01856 Da
IUPAC Namehexahydroxy-2H,2'H,5H,5'H-[5,5'-bipyrimidine]-2,2'-dione
Traditional Namehexahydroxy-[5,5'-bipyrimidine]-2,2'-dione
CAS Registry NumberNot Available
SMILES
OC1=NC(=O)N=C(O)C1(O)C1(O)C(O)=NC(=O)N=C1O
InChI Identifier
InChI=1S/C8H6N4O8/c13-1-7(19,2(14)10-5(17)9-1)8(20)3(15)11-6(18)12-4(8)16/h19-20H,(H2,9,10,13,14,17)(H2,11,12,15,16,18)
InChI KeyIWDDXZKCDHOOSF-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 NMR13C NMR Spectrum (1D, 252 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 NMR13C NMR Spectrum (1D, 75 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 NMR13C NMR Spectrum (1D, 126 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 NMR13C NMR Spectrum (1D, 176 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 NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Corbicula japonicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDiazines  
Sub ClassPyrimidines and pyrimidine derivatives  
Direct ParentBarbituric acid derivatives  
Alternative Parents
Substituents
  • Barbiturate
    • 

  • N-acyl urea
    • 

  • Ureide
    • 

  • 1,3-diazinane
    • 

  • Dicarboximide
    • 

  • Tertiary alcohol
    • 

  • 1,2-diol
    • 

  • Carbonic acid derivative
    • 

  • Urea
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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-2.5ChemAxon
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area204.96 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity53.87 m³·mol⁻¹ChemAxon
Polarizability21.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6195  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6435  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]