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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-02-22 10:05:38 UTC

Update Date

2023-02-21 17:15:50 UTC

HMDB ID

HMDB0001857

Secondary Accession Numbers

HMDB01857

Metabolite Identification

Common Name

1,3-Dimethyluric acid

Description

1,3-Dimethyluric acid is a product of theophylline metabolism in man. 1,3-Dimethyluric acid is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by 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 super-family, 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 ).

Structure

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

  Mrv1652305261923522D          

 14 15  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 N   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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001857

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=C(NC(=O)N2)C(=O)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H8N4O3/c1-10-4-3(8-6(13)9-4)5(12)11(2)7(10)14/h1-2H3,(H2,8,9,13)

> <INCHI_KEY>
OTSBKHHWSQYEHK-UHFFFAOYSA-N

> <FORMULA>
C7H8N4O3

> <MOLECULAR_WEIGHT>
196.1634

> <EXACT_MASS>
196.059640142

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.74189953059846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-1.0968408043333333

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.258942474439532

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.742717171687908

> <JCHEM_PKA_STRONGEST_BASIC>
-5.922888493165294

> <JCHEM_POLAR_SURFACE_AREA>
81.75

> <JCHEM_REFRACTIVITY>
55.422

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-dimethyluric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.465   2.016   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.910   0.770   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      -1.465  -0.476   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   10                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    7                                                            
CONECT   11    4   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    3                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Oxytheophylline	ChEBI
1,3-Dimethylate	Generator
1,3-Dimethylic acid	Generator
1,3-Dimethylurate	HMDB

Chemical Formula

C₇H₈N₄O₃

Average Molecular Weight

196.1634

Monoisotopic Molecular Weight

196.059640142

IUPAC Name

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

Traditional Name

1,3-dimethyluric acid

CAS Registry Number

944-73-0

SMILES

CN1C2=C(NC(=O)N2)C(=O)N(C)C1=O

InChI Identifier

InChI=1S/C7H8N4O3/c1-10-4-3(8-6(13)9-4)5(12)11(2)7(10)14/h1-2H3,(H2,8,9,13)

InChI Key

OTSBKHHWSQYEHK-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:68447 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 27510537)

Organ

Liver (HMDB: HMDB0001857)
Kidney (HMDB: HMDB0001857)

Excreta

Biofluid or Excreta

Urine (PMID: 15537072)
Feces (PMID: 26848182)

Cellular substructure

Cytoplasm (HMDB: HMDB0001857)

Source

Endogenous

Endogenous (HMDB: HMDB0001857)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0001857)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0001857)

Tea

Tea products (HMDB: HMDB0001857)

Process

Naturally occurring process

Biological process

Biochemical pathway

Asthma (HMDB: HMDB0001857)

Role

Biological role

Drug metabolite (HMDB: HMDB0001857)

Industrial application

Pharmaceutical industry

Biomarker

Asthma (MarkerDB: MDB00000346)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	408 - 410 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.52 mg/mL at 18 °C	Not Available
LogP	-0.52	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	134.243	30932474
[M+H]+	MetCCS_train_pos	142.525	30932474
[M-H]-	Not Available	134.243	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000344
[M+H]+	Not Available	143.059	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000344

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.69 g/L	ALOGPS
logP	-0.74	ALOGPS
logP	-1.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.75 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	55.42 m³·mol⁻¹	ChemAxon
Polarizability	17.74 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]+	142.43	31661259
DarkChem	[M-H]-	140.716	31661259
AllCCS	[M+H]+	141.236	32859911
AllCCS	[M-H]-	139.528	32859911
DeepCCS	[M+H]+	138.805	30932474
DeepCCS	[M-H]-	136.409	30932474
DeepCCS	[M-2H]-	171.136	30932474
DeepCCS	[M+Na]+	145.575	30932474
AllCCS	[M+H]+	141.2	32859911
AllCCS	[M+H-H2O]+	137.1	32859911
AllCCS	[M+NH4]+	145.1	32859911
AllCCS	[M+Na]+	146.2	32859911
AllCCS	[M-H]-	139.5	32859911
AllCCS	[M+Na-2H]-	139.9	32859911
AllCCS	[M+HCOO]-	140.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,3-Dimethyluric acid	CN1C2=C(NC(=O)N2)C(=O)N(C)C1=O	2409.3	Standard polar	33892256
1,3-Dimethyluric acid	CN1C2=C(NC(=O)N2)C(=O)N(C)C1=O	2220.8	Standard non polar	33892256
1,3-Dimethyluric acid	CN1C2=C(NC(=O)N2)C(=O)N(C)C1=O	2292.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,3-Dimethyluric acid,1TMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C)N(C)C1=O	2030.6	Semi standard non polar	33892256
1,3-Dimethyluric acid,1TMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C)N(C)C1=O	2201.2	Standard non polar	33892256
1,3-Dimethyluric acid,1TMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C)N(C)C1=O	2870.7	Standard polar	33892256
1,3-Dimethyluric acid,1TMS,isomer #2	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)[NH]2	1968.3	Semi standard non polar	33892256
1,3-Dimethyluric acid,1TMS,isomer #2	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)[NH]2	2217.6	Standard non polar	33892256
1,3-Dimethyluric acid,1TMS,isomer #2	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)[NH]2	2955.0	Standard polar	33892256
1,3-Dimethyluric acid,2TMS,isomer #1	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	1999.7	Semi standard non polar	33892256
1,3-Dimethyluric acid,2TMS,isomer #1	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2253.1	Standard non polar	33892256
1,3-Dimethyluric acid,2TMS,isomer #1	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C	2487.7	Standard polar	33892256
1,3-Dimethyluric acid,1TBDMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)N(C)C1=O	2210.4	Semi standard non polar	33892256
1,3-Dimethyluric acid,1TBDMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)N(C)C1=O	2398.3	Standard non polar	33892256
1,3-Dimethyluric acid,1TBDMS,isomer #1	CN1C(=O)C2=C([NH]C(=O)N2[Si](C)(C)C(C)(C)C)N(C)C1=O	2830.6	Standard polar	33892256
1,3-Dimethyluric acid,1TBDMS,isomer #2	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2	2182.7	Semi standard non polar	33892256
1,3-Dimethyluric acid,1TBDMS,isomer #2	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2	2421.5	Standard non polar	33892256
1,3-Dimethyluric acid,1TBDMS,isomer #2	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)[NH]2	2889.9	Standard polar	33892256
1,3-Dimethyluric acid,2TBDMS,isomer #1	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2403.8	Semi standard non polar	33892256
1,3-Dimethyluric acid,2TBDMS,isomer #1	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2670.7	Standard non polar	33892256
1,3-Dimethyluric acid,2TBDMS,isomer #1	CN1C(=O)C2=C(N(C)C1=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C	2593.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,3-Dimethyluric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kr-1900000000-572b5e917ae798f7285d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,3-Dimethyluric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,3-Dimethyluric 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 - 1,3-Dimethyluric acid 10V, Negative-QTOF	splash10-0002-0900000000-7e858efa4500086bcd70	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 20V, Negative-QTOF	splash10-0012-1900000000-1524d46953fcc6d20c7c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 40V, Negative-QTOF	splash10-0006-9200000000-b367b1622a53667ca97a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 30V, Negative-QTOF	splash10-01px-5900000000-ab0ac771da751bdacb1e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 30V, Negative-QTOF	splash10-01q0-1900000000-e48fc1c8a03d0a4a26c4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 20V, Negative-QTOF	splash10-0012-0900000000-598f50fb01c7b3d61958	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Negative-QTOF	splash10-0002-0900000000-41ed7be7644a8ea7bb0d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 40V, Negative-QTOF	splash10-0006-9100000000-1d833087dad5d5e4729a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-01ot-1900000000-bbb1123e337bff47c690	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-02mr-7900000000-fad7e7de9dee95b2d94b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-047i-6900000000-b985a0b78d94b88e5577	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 20V, Positive-QTOF	splash10-066s-4900000000-2bebf7701e7270029983	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 40V, Positive-QTOF	splash10-0a4i-9000000000-63cd602ba4ec338dced4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Positive-QTOF	splash10-0002-0900000000-85bd64c90cc931b94c6d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 40V, Positive-QTOF	splash10-0a4i-9000000000-0cdabbf6e8f8f82a9c92	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 30V, Positive-QTOF	splash10-0a4i-9300000000-bb25898e6cd1e8fd7df6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 0V, Positive-QTOF	splash10-0002-0900000000-8abc1aacd1e330f9d566	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 30V, Positive-QTOF	splash10-0a4i-9000000000-de880ba189f670404158	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 0V, Positive-QTOF	splash10-0002-0900000000-c398e5bc602974ed2c8e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Positive-QTOF	splash10-0a4i-9300000000-370654114c452519f68c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 30V, Positive-QTOF	splash10-014l-8900000000-fcc11a5a39d775601b50	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Positive-QTOF	splash10-0002-0900000000-5e9ba94ec6b6d85ef52c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Positive-QTOF	splash10-0002-0900000000-621c9fb937a1a620e4e7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,3-Dimethyluric acid 20V, Positive-QTOF	splash10-066s-3900000000-4f97c73f84de6fce24f9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethyluric acid 10V, Negative-QTOF	splash10-0002-0900000000-f5b0e3ac88c5546199d9	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	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	27543620	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	29808030	details
Urine	Detected and Quantified	4.758 +/- 2.472 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19754154	details
Urine	Detected and Quantified	7.63 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Shaykhutdinov RA,...	details
Urine	Detected and Quantified	1.5 (1.34-2.34) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15537072	details
Urine	Detected and Quantified	3.1 (1.3-6.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Inflammatory bowel disease	26848182	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	9.167 +/- 9.245 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected and Quantified	33.0 (21.8-52.0) umol/mmol creatinine	Adult (>18 years old)	Both	Asthma	15537072	details

Associated Disorders and Diseases

Disease References

Inflammatory bowel disease
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
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 ]
Asthma
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
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
600807 (Asthma)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022712

KNApSAcK ID

C00052097

Chemspider ID

63527

KEGG Compound ID

Not Available

BioCyc ID

CPD-14118

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

2822

PubChem Compound

70346

PDB ID

Not Available

ChEBI ID

68447

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000346

Good Scents ID

Not Available

References

Synthesis Reference

Taylor, Edward C.; Sowinski, Frank. Reaction of 6-amino- and 6-hydrazinopyrimidines with diethyl azodicarboxylate. New method for C-5 functionalization of pyrimidines. Journal of Organic Chemistry (1974), 39(7), 907-10.

Material Safety Data Sheet (MSDS)

Not Available

General References

Orlando R, Padrini R, Perazzi M, De Martin S, Piccoli P, Palatini P: Liver dysfunction markedly decreases the inhibition of cytochrome P450 1A2-mediated theophylline metabolism by fluvoxamine. Clin Pharmacol Ther. 2006 May;79(5):489-99. [PubMed:16678550 ]
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 ]
Miller M, Opheim KE, Raisys VA, Motulsky AG: Theophylline metabolism: variation and genetics. Clin Pharmacol Ther. 1984 Feb;35(2):170-82. [PubMed:6362955 ]
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 ]
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 ]

Showing metabocard for 1,3-Dimethyluric acid (HMDB0001857)

MOL for HMDB0001857 (1,3-Dimethyluric acid)

3D MOL for HMDB0001857 (1,3-Dimethyluric acid)

3D SDF for HMDB0001857 (1,3-Dimethyluric acid)

3D-SDF for HMDB0001857 (1,3-Dimethyluric acid)

PDB for HMDB0001857 (1,3-Dimethyluric acid)

3D PDB for HMDB0001857 (1,3-Dimethyluric acid)

SMILES for HMDB0001857 (1,3-Dimethyluric acid)

INCHI for HMDB0001857 (1,3-Dimethyluric acid)

Structure for HMDB0001857 (1,3-Dimethyluric acid)

3D Structure for HMDB0001857 (1,3-Dimethyluric acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra