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Showing NP-Card for 5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione (NP0154813)

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Record Information
Version2.0
Created at2022-09-02 11:46:42 UTC
Updated at2022-09-02 11:46:42 UTC
NP-MRD IDNP0154813
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione
Description1,3,7-Trimethyl-5-hydroxyisouric acid belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. 1,3,7-Trimethyl-5-hydroxyisouric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 1,3,7-trimethyl-5-hydroxyisouric acid.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0154813 (5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione)


  Mrv1652309022213462D          

 16 17  0  0  0  0            999 V2000
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    2.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
Download

3D MOL for NP0154813 (5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -1.9637    2.5702    0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2612    1.2938    0.1602 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631    0.0804    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359    0.1184    0.5153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823   -1.1635    0.5340 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511   -2.3815    0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1503   -1.1363    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974   -1.8811    0.8014 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756   -1.4175    0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4897   -1.9710    0.6769 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365   -0.2190   -0.3105 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2599    0.5828   -0.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7525   -0.0451   -0.4271 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3168   -0.2994   -1.7463 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1757    1.2420    0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8267    2.2639    0.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8530    3.0034   -0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0371    2.3683    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6219    3.2973    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9673   -2.5657    1.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0039   -2.3357    0.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730   -3.2534    0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8801    0.8618    0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9389    1.4865   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.0213   -1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521   -0.4785   -1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  2 15  1  0
 15 16  2  0
 15 13  1  0
 13 14  1  6
 13 11  1  0
 13  7  1  0
 12 23  1  0
 12 24  1  0
 12 25  1  0
  6 20  1  0
  6 21  1  0
  6 22  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
 14 26  1  0
M  END
Download

3D SDF for NP0154813 (5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione)


  Mrv1652309022213462D          

 16 17  0  0  0  0            999 V2000
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    2.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0154813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)N=C2N(C)C(=O)N(C)C(=O)C12O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10N4O4/c1-10-4-8(16,12(3)6(14)9-4)5(13)11(2)7(10)15/h16H,1-3H3

> <INCHI_KEY>
XNXQVRHXDIDGDT-UHFFFAOYSA-N

> <FORMULA>
C8H10N4O4

> <MOLECULAR_WEIGHT>
226.192

> <EXACT_MASS>
226.070204818

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.34611870874505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-1,3,7-trimethyl-2,3,5,6,7,8-hexahydro-1H-purine-2,6,8-trione

> <ALOGPS_LOGP>
-0.67

> <JCHEM_LOGP>
-1.394794080666667

> <ALOGPS_LOGS>
-1.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.71806768299926

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1223491293457393

> <JCHEM_POLAR_SURFACE_AREA>
93.52

> <JCHEM_REFRACTIVITY>
50.28060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0154813 (5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione)

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PDB for NP0154813 (5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione)
HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.258   3.613   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.591   1.303   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.924   1.303   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.429   5.144   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    2   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0154813 (5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione)
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SMILES for NP0154813 (5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione)
CN1C(=O)N=C2N(C)C(=O)N(C)C(=O)C12O
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INCHI for NP0154813 (5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione)
InChI=1S/C8H10N4O4/c1-10-4-8(16,12(3)6(14)9-4)5(13)11(2)7(10)15/h16H,1-3H3
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View in JSmol
Synonyms
ValueSource
1,3,7-Trimethyl-5-hydroxyisourateChEBI
1,3,7-Trimethyl-5-hydroxyisoateGenerator
1,3,7-Trimethyl-5-hydroxyisoic acidGenerator
Chemical FormulaC8H10N4O4
Average Mass226.1920 Da
Monoisotopic Mass226.07020 Da
IUPAC Name5-hydroxy-1,3,7-trimethyl-2,3,5,6,7,8-hexahydro-1H-purine-2,6,8-trione
Traditional Name5-hydroxy-1,3,7-trimethylpurine-2,6,8-trione
CAS Registry NumberNot Available
SMILES
CN1C(=O)N=C2N(C)C(=O)N(C)C(=O)C12O
InChI Identifier
InChI=1S/C8H10N4O4/c1-10-4-8(16,12(3)6(14)9-4)5(13)11(2)7(10)15/h16H,1-3H3
InChI KeyXNXQVRHXDIDGDT-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassImidazopyrimidines  
Sub ClassPurines and purine derivatives  
Direct ParentXanthines  
Alternative Parents
Substituents
  • Xanthine
    • 

  • Alpha-amino acid or derivatives
    • 

  • Purinone
    • 

  • Alkaloid or derivatives
    • 

  • N-acyl urea
    • 

  • Pyrimidone
    • 

  • Ureide
    • 

  • 1,3-diazinane
    • 

  • Pyrimidine
    • 

  • Dicarboximide
    • 

  • 3-imidazoline
    • 

  • Carbonic acid derivative
    • 

  • Urea
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Amidine
    • 

  • Carboxylic acid amidine
    • 

  • Carboxylic acid derivative
    • 

  • Carboximidamide
    • 

  • Azacycle
    • 

  • Alkanolamine
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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-0.67ALOGPS
logP-1.4ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.72ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area93.52 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.28 m³·mol⁻¹ChemAxon
Polarizability20.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
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 ID58827362  
KEGG Compound IDNot Available
BioCyc IDCPD-16697  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound118796883  
PDB IDNot Available
ChEBI ID90885  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]