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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:32 UTC

Update Date

2021-09-07 16:45:34 UTC

HMDB ID

HMDB0003099

Secondary Accession Numbers

HMDB03099

Metabolite Identification

Common Name

1-Methyluric acid

Description

1-Methyluric acid is one of the three main theophylline metabolites in man. 1-Methyluric acid is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline, and theobromine). Methyluric acids can be distinguished from uric acid via simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase, or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 superfamily, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis (PMID:11712316 , 15833286 , 3506820 , 15013152 , 4039734 , 9890610 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309042000282D          

 13 14  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 C   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    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 O   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    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
  6 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>
HMDB0003099

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)NC2=C(NC(=O)N2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12)

> <INCHI_KEY>
QFDRTQONISXGJA-UHFFFAOYSA-N

> <FORMULA>
C6H6N4O3

> <MOLECULAR_WEIGHT>
182.1368

> <EXACT_MASS>
182.043990078

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.725862137209987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

> <ALOGPS_LOGP>
-1.15

> <JCHEM_LOGP>
-1.32051687

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.880095047769107

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.671819121930137

> <JCHEM_PKA_STRONGEST_BASIC>
-6.168799154143619

> <JCHEM_POLAR_SURFACE_AREA>
90.54

> <JCHEM_REFRACTIVITY>
50.5253

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyluric acid

> <JCHEM_VEBER_RULE>
0

$$$$

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       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.864   2.073   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.530  -0.237   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.713   2.843   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.530   4.383   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5                                                       
CONECT   11    6   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Methylate	Generator
1-Methylic acid	Generator
1-Methylurate	HMDB, MeSH

Chemical Formula

C₆H₆N₄O₃

Average Molecular Weight

182.1368

Monoisotopic Molecular Weight

182.043990078

IUPAC Name

1-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

Traditional Name

1-methyluric acid

CAS Registry Number

708-79-2

SMILES

CN1C(=O)NC2=C(NC(=O)N2)C1=O

InChI Identifier

InChI=1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12)

InChI Key

QFDRTQONISXGJA-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
6-oxopurine
Purinone
Alkaloid or derivatives
Pyrimidone
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:68441 )
Purine alkaloids (C16359 )

Ontology

Disposition

Biological location

Cellular substructure

Cytoplasm

Non-excretory biofluid

Blood

Excreta

Feces
Urine

Organ

Kidney
Liver

Green lentil

Other pulses

Peas

Lentils

Lentils

Onion-family vegetables

Herb and spice mixtures

Curry powder

Cereals and cereal products

Cereals

Cereal products

Doughs

Sourdough

Leavened breads

Flat breads

Other breads

Potato bread

Sweet breads

Raisin bread

Teas

Herbal tea

Herbal teas

Taco shell
Tostada shell

Nuts

Coffee and coffee products

Coffee

Soy

Soy products

Soy bean

Baking goods

Wrappers

Wonton wrapper

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Caffeine metabolism

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5 mg/mL	Not Available
LogP	-0.57	GASPARI,F & BONATI,M (1987)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	129.179	30932474
[M-H]-	Not Available	129.179	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000355

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.23 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.54 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.53 m³·mol⁻¹	ChemAxon
Polarizability	15.73 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.827	31661259
DarkChem	[M-H]-	136.792	31661259
DeepCCS	[M+H]+	131.769	30932474
DeepCCS	[M-H]-	128.823	30932474
DeepCCS	[M-2H]-	165.535	30932474
DeepCCS	[M+Na]+	140.992	30932474
AllCCS	[M+H]+	138.8	32859911
AllCCS	[M+H-H2O]+	134.5	32859911
AllCCS	[M+NH4]+	142.8	32859911
AllCCS	[M+Na]+	144.0	32859911
AllCCS	[M-H]-	134.6	32859911
AllCCS	[M+Na-2H]-	135.0	32859911
AllCCS	[M+HCOO]-	135.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Methyluric acid	CN1C(=O)NC2=C(NC(=O)N2)C1=O	2768.8	Standard polar	33892256
1-Methyluric acid	CN1C(=O)NC2=C(NC(=O)N2)C1=O	2301.3	Standard non polar	33892256
1-Methyluric acid	CN1C(=O)NC2=C(NC(=O)N2)C1=O	2372.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Methyluric acid,1TMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)[NH]2)N([Si](C)(C)C)C1=O	2011.6	Semi standard non polar	33892256
1-Methyluric acid,1TMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)[NH]2)N([Si](C)(C)C)C1=O	2235.8	Standard non polar	33892256
1-Methyluric acid,1TMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)[NH]2)N([Si](C)(C)C)C1=O	3042.6	Standard polar	33892256
1-Methyluric acid,1TMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(=O)[NH]2	2036.5	Semi standard non polar	33892256
1-Methyluric acid,1TMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(=O)[NH]2	2221.8	Standard non polar	33892256
1-Methyluric acid,1TMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(=O)[NH]2	2945.6	Standard polar	33892256
1-Methyluric acid,1TMS,isomer #3	CN1C(=O)[NH]C2=C([NH]C(=O)N2[Si](C)(C)C)C1=O	2008.5	Semi standard non polar	33892256
1-Methyluric acid,1TMS,isomer #3	CN1C(=O)[NH]C2=C([NH]C(=O)N2[Si](C)(C)C)C1=O	2268.2	Standard non polar	33892256
1-Methyluric acid,1TMS,isomer #3	CN1C(=O)[NH]C2=C([NH]C(=O)N2[Si](C)(C)C)C1=O	3068.8	Standard polar	33892256
1-Methyluric acid,2TMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	2016.0	Semi standard non polar	33892256
1-Methyluric acid,2TMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	2237.6	Standard non polar	33892256
1-Methyluric acid,2TMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C)N([Si](C)(C)C)C1=O	2509.3	Standard polar	33892256
1-Methyluric acid,2TMS,isomer #2	CN1C(=O)C2=C(N([Si](C)(C)C)C(=O)[NH]2)N([Si](C)(C)C)C1=O	1990.6	Semi standard non polar	33892256
1-Methyluric acid,2TMS,isomer #2	CN1C(=O)C2=C(N([Si](C)(C)C)C(=O)[NH]2)N([Si](C)(C)C)C1=O	2296.2	Standard non polar	33892256
1-Methyluric acid,2TMS,isomer #2	CN1C(=O)C2=C(N([Si](C)(C)C)C(=O)[NH]2)N([Si](C)(C)C)C1=O	2602.1	Standard polar	33892256
1-Methyluric acid,2TMS,isomer #3	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2001.2	Semi standard non polar	33892256
1-Methyluric acid,2TMS,isomer #3	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2268.7	Standard non polar	33892256
1-Methyluric acid,2TMS,isomer #3	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2562.0	Standard polar	33892256
1-Methyluric acid,3TMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C)C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2126.4	Semi standard non polar	33892256
1-Methyluric acid,3TMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C)C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2280.0	Standard non polar	33892256
1-Methyluric acid,3TMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C)C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2287.9	Standard polar	33892256
1-Methyluric acid,1TBDMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O	2198.5	Semi standard non polar	33892256
1-Methyluric acid,1TBDMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O	2464.4	Standard non polar	33892256
1-Methyluric acid,1TBDMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O	2969.9	Standard polar	33892256
1-Methyluric acid,1TBDMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2	2224.3	Semi standard non polar	33892256
1-Methyluric acid,1TBDMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2	2428.6	Standard non polar	33892256
1-Methyluric acid,1TBDMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2	2903.2	Standard polar	33892256
1-Methyluric acid,1TBDMS,isomer #3	CN1C(=O)[NH]C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C1=O	2193.8	Semi standard non polar	33892256
1-Methyluric acid,1TBDMS,isomer #3	CN1C(=O)[NH]C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C1=O	2464.5	Standard non polar	33892256
1-Methyluric acid,1TBDMS,isomer #3	CN1C(=O)[NH]C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)C1=O	2997.6	Standard polar	33892256
1-Methyluric acid,2TBDMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O	2407.5	Semi standard non polar	33892256
1-Methyluric acid,2TBDMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O	2656.4	Standard non polar	33892256
1-Methyluric acid,2TBDMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O	2581.5	Standard polar	33892256
1-Methyluric acid,2TBDMS,isomer #2	CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O	2403.4	Semi standard non polar	33892256
1-Methyluric acid,2TBDMS,isomer #2	CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O	2702.2	Standard non polar	33892256
1-Methyluric acid,2TBDMS,isomer #2	CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(=O)[NH]2)N([Si](C)(C)C(C)(C)C)C1=O	2634.9	Standard polar	33892256
1-Methyluric acid,2TBDMS,isomer #3	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2391.3	Semi standard non polar	33892256
1-Methyluric acid,2TBDMS,isomer #3	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2689.4	Standard non polar	33892256
1-Methyluric acid,2TBDMS,isomer #3	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2619.4	Standard polar	33892256
1-Methyluric acid,3TBDMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2627.1	Semi standard non polar	33892256
1-Methyluric acid,3TBDMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2912.7	Standard non polar	33892256
1-Methyluric acid,3TBDMS,isomer #1	CN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2593.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyluric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0far-2900000000-7c88ba8c892ca8263473	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyluric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyluric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-001i-0900000000-f2e42cd67ce1106bed63	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-0900000000-9fd2304504c5787dc255	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4i-9000000000-6069b457c0c038edb8df	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Linear Ion Trap , positive-QTOF	splash10-0006-0900000000-f47eba015e7f8d9f21a7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 4V, negative-QTOF	splash10-001i-0900000000-26da10b11bacabae0d00	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 5V, negative-QTOF	splash10-001i-0900000000-dceee0216914a6ad0349	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 6V, negative-QTOF	splash10-001r-0900000000-cb9d81f2cc810b6a1bf6	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 8V, negative-QTOF	splash10-0019-2900000000-79ddb513e243e4fd1054	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 10V, negative-QTOF	splash10-001a-7900000000-aeb7c72625ab71bbfcb3	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid n/a 12V, negative-QTOF	splash10-000i-0900000000-72f91c756d76768ecc23	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid n/a 12V, negative-QTOF	splash10-004i-9000000000-0ae8d2338f48c17984cd	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid n/a 12V, negative-QTOF	splash10-001i-9400000000-943dd572fd686e87913d	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 1V, negative-QTOF	splash10-03di-0109000000-cf0f38f1f9c792f0404d	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 1V, negative-QTOF	splash10-03di-0309000000-9a8aaf68c144b67fbc6e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 2V, negative-QTOF	splash10-01q9-0905000000-d40f59a74d4b8cc4e1d6	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 3V, negative-QTOF	splash10-001i-0901000000-265af2cad1ab697d3249	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 3V, negative-QTOF	splash10-001i-0900000000-2b4e4dd83c0bad2269ae	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 4V, negative-QTOF	splash10-001i-0900000000-c37839583f5e4e15cc46	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyluric acid Orbitrap 9V, negative-QTOF	splash10-001i-0900000000-6254efb7ddc081f6fd0c	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyluric acid 10V, Positive-QTOF	splash10-001i-0900000000-9fb7b528d968cab88bd3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyluric acid 20V, Positive-QTOF	splash10-0059-1900000000-eb2d1569b5bdfeef979a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyluric acid 40V, Positive-QTOF	splash10-000w-9300000000-065aa3463c121bf31312	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyluric acid 10V, Negative-QTOF	splash10-001i-1900000000-62dd716e79c8fa6f5ee0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyluric acid 20V, Negative-QTOF	splash10-001i-3900000000-bf85a8ad5b7719f36aba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyluric acid 40V, Negative-QTOF	splash10-0006-9100000000-7db60439b29417bbbe0d	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, 5%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Amniotic Fluid
Blood
Feces
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Caffeine Metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Amniotic Fluid	Detected and Quantified	0.51 +/- 0.044 uM	Adult (>18 years old)	Both	Normal	16139832	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24801555	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25762808	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	13.95 +/- 10.65 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	16139832	details
Urine	Detected and Quantified	25.20 +/- 13.5 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	16139832	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	7.04 +/- 1.57 umol/mmol creatinine	Adult (>18 years old)	Both	Canavan disease	16139832	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
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 ] 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 ]
Canavan disease
Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]

Associated OMIM IDs

114500 (Colorectal cancer)
271900 (Canavan disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023107

KNApSAcK ID

Not Available

Chemspider ID

62926

KEGG Compound ID

C16359

BioCyc ID

CPD-14119

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

2821

PubChem Compound

69726

PDB ID

Not Available

ChEBI ID

68441

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000410

Good Scents ID

Not Available

References

Synthesis Reference

Prusse, August. Synthesis of methylated uric acids according to Behrend and Roosen. Ann. (1925), 441 203-15.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Knoppert DC, Spino M, Beck R, Thiessen JJ, MacLeod SM: Cystic fibrosis: enhanced theophylline metabolism may be linked to the disease. Clin Pharmacol Ther. 1988 Sep;44(3):254-64. [PubMed:3046811 ]
Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [PubMed:3506820 ]
Tateishi T, Asoh M, Yamaguchi A, Yoda T, Okano YJ, Koitabashi Y, Kobayashi S: Developmental changes in urinary elimination of theophylline and its metabolites in pediatric patients. Pediatr Res. 1999 Jan;45(1):66-70. [PubMed:9890610 ]
Nakano K, Assenza SP, Brown PR: Reversed-phase liquid chromatographic investigation of UV-absorbing low-molecular-weight compounds in saliva. J Chromatogr. 1982 Dec 10;233:51-60. [PubMed:7161362 ]
Grygiel JJ, Wing LM, Farkas J, Birkett DJ: Effects of allopurinol on theophylline metabolism and clearance. Clin Pharmacol Ther. 1979 Nov;26(5):660-7. [PubMed:498708 ]
Kilbane AJ, Silbart LK, Manis M, Beitins IZ, Weber WW: Human N-acetylation genotype determination with urinary caffeine metabolites. Clin Pharmacol Ther. 1990 Apr;47(4):470-7. [PubMed:2328555 ]
Safranow K, Machoy Z: Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 May 25;819(2):229-35. [PubMed:15833286 ]
Safranow K: [Identification and quantitation of purine derivatives in urinary calculi as markers of abnormal purine metabolism by using high-performance liquid chromatography (HPLC)]. Ann Acad Med Stetin. 2000;46:35-49. [PubMed:11712316 ]
Caubet MS, Comte B, Brazier JL: Determination of urinary 13C-caffeine metabolites by liquid chromatography-mass spectrometry: the use of metabolic ratios to assess CYP1A2 activity. J Pharm Biomed Anal. 2004 Feb 4;34(2):379-89. [PubMed:15013152 ]
Miller CA, Slusher LB, Vesell ES: Polymorphism of theophylline metabolism in man. J Clin Invest. 1985 May;75(5):1415-25. [PubMed:4039734 ]

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

1-Methylxanthine + Water + Oxygen → 1-Methyluric acid + Hydrogen peroxide	details

Showing metabocard for 1-Methyluric acid (HMDB0003099)

MOL for HMDB0003099 (1-Methyluric acid)

3D MOL for HMDB0003099 (1-Methyluric acid)

3D SDF for HMDB0003099 (1-Methyluric acid)

3D-SDF for HMDB0003099 (1-Methyluric acid)

PDB for HMDB0003099 (1-Methyluric acid)

3D PDB for HMDB0003099 (1-Methyluric acid)

SMILES for HMDB0003099 (1-Methyluric acid)

INCHI for HMDB0003099 (1-Methyluric acid)

Structure for HMDB0003099 (1-Methyluric acid)

3D Structure for HMDB0003099 (1-Methyluric acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions