Showing NP-Card for Paraxanthine (NP0000047)

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Record Information
Version2.0
Created at2006-02-22 11:10:26 UTC
Updated at2021-06-29 00:47:13 UTC
NP-MRD IDNP0000047
Secondary Accession NumbersNone
Natural Product Identification
Common NameParaxanthine
DescriptionParaxanthine, also known as p-xanthine, 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. Paraxanthine exists in all living organisms, ranging from bacteria to humans. Within humans, paraxanthine participates in a number of enzymatic reactions. In particular, paraxanthine and formaldehyde can be biosynthesized from caffeine; which is catalyzed by the enzyme cytochrome P450 1A2. In addition, paraxanthine and acetyl-CoA can be converted into 5-acetylamino-6-formylamino-3-methyluracil through its interaction with the enzyme arylamine N-acetyltransferase 2. In humans, paraxanthine is involved in caffeine metabolism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000047 (Paraxanthine)

  Mrv1652309042000252D          

 13 14  0  0  0  0            999 V2000
   12.5271  -15.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3441  -16.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7571  -17.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4875  -16.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4875  -17.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -16.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0586  -17.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2721  -17.9676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -18.1252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2721  -16.6327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0586  -16.8877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -15.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3441  -18.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3 10  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 12  2  0  0  0  0
  6 11  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
Download

3D MOL for NP0000047 (Paraxanthine)

HMDB0001860
     RDKit          3D
Paraxanthine
 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.7364   -1.4248   -0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7022   -0.4165   -0.1122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304    0.8641    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2484    1.1780    0.1665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871    1.8176    0.3293 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2279    1.5556    0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628    2.2572    0.4588 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4337    1.4543    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344    0.2298    0.0789 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -0.9610   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919    0.2409    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3891   -0.7131   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0229   -1.9035   -0.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -2.3529   -0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640   -1.1161   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673   -1.5475    0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    2.8180    0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4915    1.7412    0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8297   -1.4535    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7316   -0.6494   -0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2401   -1.6185   -0.8798 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12  2  1  0
 11  6  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  8 18  1  0
 10 19  1  0
 10 20  1  0
 10 21  1  0
M  END
Download

3D SDF for NP0000047 (Paraxanthine)

  Mrv1652309042000252D          

 13 14  0  0  0  0            999 V2000
   12.5271  -15.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3441  -16.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7571  -17.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4875  -16.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4875  -17.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -16.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0586  -17.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2721  -17.9676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -18.1252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2721  -16.6327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0586  -16.8877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -15.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3441  -18.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3 10  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 12  2  0  0  0  0
  6 11  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000047

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC2=C1C(=O)N(C)C(=O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)

> <INCHI_KEY>
QUNWUDVFRNGTCO-UHFFFAOYSA-N

> <FORMULA>
C7H8N4O2

> <MOLECULAR_WEIGHT>
180.164

> <EXACT_MASS>
180.06472552

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.865495165097393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

> <ALOGPS_LOGP>
-0.63

> <JCHEM_LOGP>
0.24028833966666654

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.761286686077602

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8667931938763297

> <JCHEM_POLAR_SURFACE_AREA>
67.23

> <JCHEM_REFRACTIVITY>
46.715300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
paraxanthine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000047 (Paraxanthine)

HMDB0001860
     RDKit          3D
Paraxanthine
 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.7364   -1.4248   -0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7022   -0.4165   -0.1122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304    0.8641    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2484    1.1780    0.1665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871    1.8176    0.3293 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2279    1.5556    0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628    2.2572    0.4588 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4337    1.4543    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344    0.2298    0.0789 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -0.9610   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919    0.2409    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3891   -0.7131   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0229   -1.9035   -0.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -2.3529   -0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640   -1.1161   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673   -1.5475    0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    2.8180    0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4915    1.7412    0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8297   -1.4535    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7316   -0.6494   -0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2401   -1.6185   -0.8798 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12  2  1  0
 11  6  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  8 18  1  0
 10 19  1  0
 10 20  1  0
 10 21  1  0
M  END
Download

PDB for NP0000047 (Paraxanthine)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      23.384 -29.583   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.442 -30.754   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.813 -32.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.443 -31.524   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.443 -33.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.110 -30.754   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.776 -33.064   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      22.908 -33.540   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      20.110 -33.834   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      22.908 -31.048   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      18.776 -31.524   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      20.110 -29.214   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      17.442 -33.834   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   10    8                                                       
CONECT    4    5   10    6                                                  
CONECT    5    4    8    9                                                  
CONECT    6    4   12   11                                                  
CONECT    7   11   13    9                                                  
CONECT    8    3    5                                                       
CONECT    9    5    7                                                       
CONECT   10    1    3    4                                                  
CONECT   11    2    6    7                                                  
CONECT   12    6                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for NP0000047 (Paraxanthine)

COMPND    HMDB0001860
HETATM    1  C1  UNL     1      -2.736  -1.425  -0.325  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.702  -0.416  -0.112  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.030   0.864   0.128  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.248   1.178   0.166  1.00  0.00           O  
HETATM    5  N2  UNL     1      -1.087   1.818   0.329  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.228   1.556   0.303  1.00  0.00           C  
HETATM    7  N3  UNL     1       1.363   2.257   0.459  1.00  0.00           N  
HETATM    8  C4  UNL     1       2.434   1.454   0.324  1.00  0.00           C  
HETATM    9  N4  UNL     1       1.934   0.230   0.079  1.00  0.00           N  
HETATM   10  C5  UNL     1       2.739  -0.961  -0.136  1.00  0.00           C  
HETATM   11  C6  UNL     1       0.592   0.241   0.056  1.00  0.00           C  
HETATM   12  C7  UNL     1      -0.389  -0.713  -0.145  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.023  -1.903  -0.368  1.00  0.00           O  
HETATM   14  H1  UNL     1      -2.262  -2.353  -0.671  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.464  -1.116  -1.081  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.267  -1.547   0.640  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.373   2.818   0.517  1.00  0.00           H  
HETATM   18  H5  UNL     1       3.492   1.741   0.398  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.830  -1.454   0.860  1.00  0.00           H  
HETATM   20  H7  UNL     1       3.732  -0.649  -0.542  1.00  0.00           H  
HETATM   21  H8  UNL     1       2.240  -1.619  -0.880  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   12
CONECT    3    4    4    5
CONECT    5    6   17
CONECT    6    7   11   11
CONECT    7    8    8
CONECT    8    9   18
CONECT    9   10   11
CONECT   10   19   20   21
CONECT   11   12
CONECT   12   13   13
END
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SMILES for NP0000047 (Paraxanthine)

CN1C=NC2=C1C(=O)N(C)C(=O)N2
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INCHI for NP0000047 (Paraxanthine)

InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
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View in JSmol
Synonyms
ValueSource
3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dioneChEBI
p-XanthineChEBI
1,7-Dimethyl-xanthineHMDB
1,7-DimethylxanthineHMDB
Chemical FormulaC7H8N4O2
Average Mass180.1640 Da
Monoisotopic Mass180.06473 Da
IUPAC Name1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nameparaxanthine
CAS Registry Number611-59-6
SMILES
CN1C=NC2=C1C(=O)N(C)C(O)=N2
InChI Identifier
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
InChI KeyQUNWUDVFRNGTCO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
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
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point351 - 352 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.13 g/LALOGPS
logP-0.63ALOGPS
logP0.24ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.76ChemAxon
pKa (Strongest Basic)-0.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.72 m³·mol⁻¹ChemAxon
Polarizability16.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001860
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022714
KNApSAcK IDC00039930
Chemspider ID4525
KEGG Compound IDC13747
BioCyc ID1-7-DIMETHYLXANTHINE
BiGG IDNot Available
Wikipedia LinkParaxanthine
METLIN ID1457
PubChem Compound4687
PDB IDNot Available
ChEBI ID25858
Good Scents IDNot Available
References
General References