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Showing metabocard for Paraxanthine (HMDB0001860)

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enzymes (28) Show 28 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-22 11:10:26 UTC
Update Date2023-02-21 17:15:51 UTC
HMDB IDHMDB0001860
Secondary Accession Numbers
  • HMDB01860
Metabolite 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
Data?1676999751
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001860 (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
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3D MOL for HMDB0001860 (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 HMDB0001860 (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>
HMDB0001860

> <DATABASE_NAME>
hmdb

> <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 HMDB0001860 (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
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PDB for HMDB0001860 (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 HMDB0001860 (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 HMDB0001860 (Paraxanthine)

CN1C=NC2=C1C(=O)N(C)C(=O)N2
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INCHI for HMDB0001860 (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 JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dioneChEBI
p-XanthineChEBI
1,7-Dimethyl-xanthineHMDB
1,7-DimethylxanthineHMDB, MeSH
Chemical FormulaC7H8N4O2
Average Molecular Weight180.164
Monoisotopic Molecular Weight180.06472552
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
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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point351 - 352 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Baker135.62530932474
[M-H]-Not Available133.24http://allccs.zhulab.cn/database/detail?ID=AllCCS00000345
[M+H]+Not Available135.625http://allccs.zhulab.cn/database/detail?ID=AllCCS00000345
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.38531661259
DarkChem[M-H]-137.3631661259
AllCCS[M+H]+138.46732859911
AllCCS[M-H]-136.81132859911
DeepCCS[M+H]+134.44230932474
DeepCCS[M-H]-131.85630932474
DeepCCS[M-2H]-167.81330932474
DeepCCS[M+Na]+143.1430932474
AllCCS[M+H]+138.532859911
AllCCS[M+H-H2O]+134.232859911
AllCCS[M+NH4]+142.532859911
AllCCS[M+Na]+143.632859911
AllCCS[M-H]-136.832859911
AllCCS[M+Na-2H]-137.432859911
AllCCS[M+HCOO]-138.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.5 minutes32390414
Predicted by Siyang on May 30, 20228.9648 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.68 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid34.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid711.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid294.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid79.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid174.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid53.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid259.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid295.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)92.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid609.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid289.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid774.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid197.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid178.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate570.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA182.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water128.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ParaxanthineCN1C=NC2=C1C(=O)N(C)C(=O)N22382.3Standard polar33892256
ParaxanthineCN1C=NC2=C1C(=O)N(C)C(=O)N21867.7Standard non polar33892256
ParaxanthineCN1C=NC2=C1C(=O)N(C)C(=O)N22065.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Paraxanthine,1TMS,isomer #1CN1C(=O)C2=C(N=CN2C)N([Si](C)(C)C)C1=O1875.3Semi standard non polar33892256
Paraxanthine,1TMS,isomer #1CN1C(=O)C2=C(N=CN2C)N([Si](C)(C)C)C1=O2088.9Standard non polar33892256
Paraxanthine,1TMS,isomer #1CN1C(=O)C2=C(N=CN2C)N([Si](C)(C)C)C1=O2612.9Standard polar33892256
Paraxanthine,1TBDMS,isomer #1CN1C(=O)C2=C(N=CN2C)N([Si](C)(C)C(C)(C)C)C1=O2095.9Semi standard non polar33892256
Paraxanthine,1TBDMS,isomer #1CN1C(=O)C2=C(N=CN2C)N([Si](C)(C)C(C)(C)C)C1=O2279.3Standard non polar33892256
Paraxanthine,1TBDMS,isomer #1CN1C(=O)C2=C(N=CN2C)N([Si](C)(C)C(C)(C)C)C1=O2605.4Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified10.0 (0.30-28.0) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified3.44 +/- 2 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.5 (3.2-4.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma 		details
Cerebrospinal Fluid (CSF)Detected and Quantified1.780 +/- 0.641 uMAdult (>18 years old)Not SpecifiedFavorable outcome from traumatic brain injury details
Cerebrospinal Fluid (CSF)Detected and Quantified0.833 +/- 1.163 uMAdult (>18 years old)MaleTraumatic Brain Injury (TBI) details
Cerebrospinal Fluid (CSF)Detected and Quantified1.200 +/- 1.373 uMAdult (>18 years old)FemaleTraumatic Brain Injury (TBI) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.703 +/- 0.230 uMAdult (>18 years old)Not Specified
Traumatic brain injury		 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.931 +/- 0.221 uMAdult (>18 years old)Not SpecifiedTraumatic brain injury (TBI) details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified3.6 (1.8-5.4) umol/mmol creatinineAdult (>18 years old)Both
Asthma		 details
UrineDetected and Quantified18.676 +/- 26.196 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma 		details
Associated Disorders and Diseases
Disease References
Traumatic brain injury
  1. Sachse KT, Jackson EK, Wisniewski SR, Gillespie DG, Puccio AM, Clark RS, Dixon CE, Kochanek PM: Increases in cerebrospinal fluid caffeine concentration are associated with favorable outcome after severe traumatic brain injury in humans. J Cereb Blood Flow Metab. 2008 Feb;28(2):395-401. Epub 2007 Aug 8. [PubMed:17684518 ]
Head injury
  1. Sachse KT, Jackson EK, Wisniewski SR, Gillespie DG, Puccio AM, Clark RS, Dixon CE, Kochanek PM: Increases in cerebrospinal fluid caffeine concentration are associated with favorable outcome after severe traumatic brain injury in humans. J Cereb Blood Flow Metab. 2008 Feb;28(2):395-401. Epub 2007 Aug 8. [PubMed:17684518 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Asthma
  1. Zydron M, Baranowski J, Baranowska I: Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. J Sep Sci. 2004 Oct;27(14):1166-72. [PubMed:15537072 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMueller, Christa E.; Deters, Dirk; Dominik, Andreas; Pawlowski, Maciej. Synthesis of paraxanthine and isoparaxanthine analogs (1,7- and 1,9-substituted xanthine derivatives). Synthesis (1998), (10), 1428-1436.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Christensen M, Andersson K, Dalen P, Mirghani RA, Muirhead GJ, Nordmark A, Tybring G, Wahlberg A, Yasar U, Bertilsson L: The Karolinska cocktail for phenotyping of five human cytochrome P450 enzymes. Clin Pharmacol Ther. 2003 Jun;73(6):517-28. [PubMed:12811361 ]
  3. Fuhr U, Rost KL: Simple and reliable CYP1A2 phenotyping by the paraxanthine/caffeine ratio in plasma and in saliva. Pharmacogenetics. 1994 Jun;4(3):109-16. [PubMed:7920690 ]
  4. Tanaka E: Simultaneous determination of caffeine and its primary demethylated metabolites in human plasma by high-performance liquid chromatography. J Chromatogr. 1992 Mar 27;575(2):311-4. [PubMed:1629311 ]
  5. Horrigan LA, Kelly JP, Connor TJ: Immunomodulatory effects of caffeine: friend or foe? Pharmacol Ther. 2006 Sep;111(3):877-92. Epub 2006 Mar 15. [PubMed:16540173 ]
  6. Holstege A, Kurz M, Weinbeck M, Gerok W: Excretion of caffeine and its primary degradation products into bile. J Hepatol. 1993 Jan;17(1):67-73. [PubMed:8445222 ]
  7. Granfors MT, Backman JT, Laitila J, Neuvonen PJ: Oral contraceptives containing ethinyl estradiol and gestodene markedly increase plasma concentrations and effects of tizanidine by inhibiting cytochrome P450 1A2. Clin Pharmacol Ther. 2005 Oct;78(4):400-11. [PubMed:16198659 ]
  8. Blanchard J, Weber CW, Shearer LE: HPLC analysis of methylxanthines in human breast milk. J Chromatogr Sci. 1990 Dec;28(12):640-2. [PubMed:2292610 ]
  9. Delahunty T, Schoendorfer D: Caffeine demethylation monitoring using a transdermal sweat patch. J Anal Toxicol. 1998 Nov-Dec;22(7):596-600. [PubMed:9847011 ]
  10. Holland DT, Godfredsen KA, Page T, Connor JD: Simple high-performance liquid chromatography method for the simultaneous determination of serum caffeine and paraxanthine following rapid sample preparation. J Chromatogr B Biomed Sci Appl. 1998 Apr 10;707(1-2):105-10. [PubMed:9613939 ]
  11. Fuhr U, Rost KL, Engelhardt R, Sachs M, Liermann D, Belloc C, Beaune P, Janezic S, Grant D, Meyer UA, Staib AH: Evaluation of caffeine as a test drug for CYP1A2, NAT2 and CYP2E1 phenotyping in man by in vivo versus in vitro correlations. Pharmacogenetics. 1996 Apr;6(2):159-76. [PubMed:9156694 ]
  12. Zaigler M, Rietbrock S, Szymanski J, Dericks-Tan JS, Staib AH, Fuhr U: Variation of CYP1A2-dependent caffeine metabolism during menstrual cycle in healthy women. Int J Clin Pharmacol Ther. 2000 May;38(5):235-44. [PubMed:10839467 ]
  13. Blanchard J, Weber CW, Shearer LE: Methylxanthine levels in breast milk of lactating women of different ethnic and socioeconomic classes. Biopharm Drug Dispos. 1992 Apr;13(3):187-96. [PubMed:1576327 ]
  14. Wahllander A, Renner E, Karlaganis G: High-performance liquid chromatographic determination of dimethylxanthine metabolites of caffeine in human plasma. J Chromatogr. 1985 Mar 22;338(2):369-75. [PubMed:3998024 ]
  15. Koch JP, ten Tusscher GW, Koppe JG, Guchelaar HJ: Validation of a high-performance liquid chromatography assay for quantification of caffeine and paraxanthine in human serum in the context of CYP1A2 phenotyping. Biomed Chromatogr. 1999 Jun;13(4):309-14. [PubMed:10416066 ]
  16. Sachse C, Ruschen S, Dettling M, Schley J, Bauer S, Muller-Oerlinghausen B, Roots I, Brockmoller J: Flavin monooxygenase 3 (FMO3) polymorphism in a white population: allele frequencies, mutation linkage, and functional effects on clozapine and caffeine metabolism. Clin Pharmacol Ther. 1999 Oct;66(4):431-8. [PubMed:10546928 ]
  17. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 28 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Arylamine N-acetyltransferase 1
General function:
Involved in acetyltransferase activity
Specific function:
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:
NAT1
Uniprot ID:
P18440
Molecular weight:
33898.445
Reactions
Paraxanthine → 5-Acetylamino-6-formylamino-3-methyluracildetails
Enzyme Details
2. Arylamine N-acetyltransferase 2
General function:
Involved in acetyltransferase activity
Specific function:
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:
NAT2
Uniprot ID:
P11245
Molecular weight:
33570.245
Reactions
Paraxanthine → 5-Acetylamino-6-formylamino-3-methyluracildetails
Enzyme Details
3. Xanthine dehydrogenase/oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
Reactions
Paraxanthine + Oxygen + Water → 1,7-Dimethyluric acid + Hydrogen peroxidedetails
Enzyme Details
4. Cytochrome P450 3A4
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
Enzyme Details
5. Cytochrome P450 2C9
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
Enzyme Details
6. Cytochrome P450 2C19
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
Enzyme Details
7. Cytochrome P450 2E1
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
Enzyme Details
8. Cytochrome P450 3A43
General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
Enzyme Details
9. Cytochrome P450 1B1
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
Enzyme Details
10. Cytochrome P450 2C18
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075

Only showing the first 10 proteins. There are 28 proteins in total.

Show all enzymes and transporters