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Showing metabocard for 7-Methyluric acid (HMDB0011107)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2008-10-16 22:26:25 UTC
Update Date2023-02-21 17:17:27 UTC
HMDB IDHMDB0011107
Secondary Accession Numbers
  • HMDB11107
Metabolite Identification
Common Name7-Methyluric acid
Description7-Methyluric acid, also known as 7-methylate, 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. 7-Methyluric acid is the minor urinary metabolites of caffeine. 7-Methyluric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 7-Methyluric acid exists in all living organisms, ranging from bacteria to humans. 7-methyluric acid can be biosynthesized from 7-methylxanthine through its interaction with the enzyme xanthine dehydrogenase/oxidase. In humans, 7-methyluric acid is involved in caffeine metabolism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0011107 (7-Methyluric acid)

  Mrv1652309042000342D          

 13 14  0  0  0  0            999 V2000
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
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3D MOL for HMDB0011107 (7-Methyluric acid)

HMDB0011107
     RDKit          3D
7-Methyluric acid
 19 20  0  0  0  0  0  0  0  0999 V2000
   -2.5581   -0.5835    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3861    0.2561   -0.0939 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3609    1.5791   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256    2.2639   -0.4043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977    1.9761   -0.5278 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271    0.9226   -0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0565    0.7144   -0.4485 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890   -0.5178   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8340   -0.6899   -0.3125 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8187   -1.5881    0.0177 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909   -1.3874    0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2825   -2.3480    0.3275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1002   -0.1536   -0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4424   -1.5184   -0.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5569   -0.7940    1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4583   -0.0642   -0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2197    2.9354   -0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832    1.5333   -0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2494   -2.5358    0.1688 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  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13  2  1  0
 13  6  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  7 18  1  0
 10 19  1  0
M  END
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3D SDF for HMDB0011107 (7-Methyluric acid)

  Mrv1652309042000342D          

 13 14  0  0  0  0            999 V2000
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011107

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)NC2=C1C(=O)NC(=O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N4O3/c1-10-2-3(8-6(10)13)7-5(12)9-4(2)11/h1H3,(H3,7,8,9,11,12,13)

> <INCHI_KEY>
YHNNPKUFPWLTOP-UHFFFAOYSA-N

> <FORMULA>
C6H6N4O3

> <MOLECULAR_WEIGHT>
182.1368

> <EXACT_MASS>
182.043990078

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
16.00351140913572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-methyl-7H-purine-2,6,8-triol

> <ALOGPS_LOGP>
-1.03

> <JCHEM_LOGP>
0.931471851

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.75778117919651

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.657959565973655

> <JCHEM_PKA_STRONGEST_BASIC>
-1.068390802761709

> <JCHEM_POLAR_SURFACE_AREA>
104.29

> <JCHEM_REFRACTIVITY>
43.77779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-methyluric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0011107 (7-Methyluric acid)

HMDB0011107
     RDKit          3D
7-Methyluric acid
 19 20  0  0  0  0  0  0  0  0999 V2000
   -2.5581   -0.5835    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3861    0.2561   -0.0939 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3609    1.5791   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256    2.2639   -0.4043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977    1.9761   -0.5278 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271    0.9226   -0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0565    0.7144   -0.4485 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890   -0.5178   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8340   -0.6899   -0.3125 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8187   -1.5881    0.0177 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909   -1.3874    0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2825   -2.3480    0.3275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1002   -0.1536   -0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4424   -1.5184   -0.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5569   -0.7940    1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4583   -0.0642   -0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2197    2.9354   -0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832    1.5333   -0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2494   -2.5358    0.1688 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  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13  2  1  0
 13  6  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  7 18  1  0
 10 19  1  0
M  END
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PDB for HMDB0011107 (7-Methyluric acid)

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      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.530   0.237   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       3.864  -2.073   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    4   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0011107 (7-Methyluric acid)

COMPND    HMDB0011107
HETATM    1  C1  UNL     1      -2.558  -0.584   0.160  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.386   0.256  -0.094  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.361   1.579  -0.353  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.426   2.264  -0.404  1.00  0.00           O  
HETATM    5  N2  UNL     1      -0.098   1.976  -0.528  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.727   0.923  -0.387  1.00  0.00           C  
HETATM    7  N3  UNL     1       2.056   0.714  -0.449  1.00  0.00           N  
HETATM    8  C4  UNL     1       2.589  -0.518  -0.250  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.834  -0.690  -0.312  1.00  0.00           O  
HETATM   10  N4  UNL     1       1.819  -1.588   0.018  1.00  0.00           N  
HETATM   11  C5  UNL     1       0.491  -1.387   0.081  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.282  -2.348   0.328  1.00  0.00           O  
HETATM   13  C6  UNL     1      -0.100  -0.154  -0.113  1.00  0.00           C  
HETATM   14  H1  UNL     1      -2.442  -1.518  -0.421  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.557  -0.794   1.242  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.458  -0.064  -0.184  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.220   2.935  -0.739  1.00  0.00           H  
HETATM   18  H5  UNL     1       2.683   1.533  -0.656  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.249  -2.536   0.169  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   13
CONECT    3    4    4    5
CONECT    5    6   17
CONECT    6    7   13   13
CONECT    7    8   18
CONECT    8    9    9   10
CONECT   10   11   19
CONECT   11   12   12   13
END
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SMILES for HMDB0011107 (7-Methyluric acid)

CN1C(=O)NC2=C1C(=O)NC(=O)N2
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INCHI for HMDB0011107 (7-Methyluric acid)

InChI=1S/C6H6N4O3/c1-10-2-3(8-6(10)13)7-5(12)9-4(2)11/h1H3,(H3,7,8,9,11,12,13)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
7-MethylateGenerator
7-Methylic acidGenerator
Chemical FormulaC6H6N4O3
Average Molecular Weight182.1368
Monoisotopic Molecular Weight182.043990078
IUPAC Name7-methyl-7H-purine-2,6,8-triol
Traditional Name7-methyluric acid
CAS Registry NumberNot Available
SMILES
CN1C(=O)NC2=C1C(=O)NC(=O)N2
InChI Identifier
InChI=1S/C6H6N4O3/c1-10-2-3(8-6(10)13)7-5(12)9-4(2)11/h1H3,(H3,7,8,9,11,12,13)
InChI KeyYHNNPKUFPWLTOP-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
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot 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]-MetCCS_train_neg129.34830932474
[M-H]-Not Available129.348http://allccs.zhulab.cn/database/detail?ID=AllCCS00000362
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027890
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16355
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound69160
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 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
7-Methylxanthine + Oxygen + Water → 7-Methyluric acid + Hydrogen peroxidedetails