MiMeDB: Showing metabocard for 1,7-Dimethyluric acid (MMDBc0000443)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:52 UTC

Update Date

2024-04-30 19:32:25 UTC

Metabolite ID

MMDBc0000443

Metabolite Identification

Common Name

1,7-Dimethyluric acid

Description

1,7-Dimethyluric acid is the major urinary caffeine metabolite that is produced in the human body. 1,7-Dimethyluric acid is formed during caffeine metabolism and the process is catalyzed primarily by CYP2A6 (PMID: 18715882 ).

Structure

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


  Mrv1652309042000332D          

 14 15  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
   -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
    1.3556    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
    2.7845   -1.5229    0.0000 C   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
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000443

> <DATABASE_NAME>
MIME

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

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

> <INCHI_KEY>
NOFNCLGCUJJPKU-UHFFFAOYSA-N

> <FORMULA>
C7H8N4O3

> <MOLECULAR_WEIGHT>
196.1634

> <EXACT_MASS>
196.059640142

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.06105286981368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,8-dihydroxy-1,7-dimethyl-6,7-dihydro-1H-purin-6-one

> <ALOGPS_LOGP>
-0.81

> <JCHEM_LOGP>
0.47086302666666646

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.480737061798054

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9649633548664176

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8635946742632101

> <JCHEM_POLAR_SURFACE_AREA>
90.95

> <JCHEM_REFRACTIVITY>
48.9246

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,7-dimethyluric 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      -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      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       2.530   0.237   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       3.864  -2.073   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11    3   13                                                  
CONECT   13   12                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

Synonyms

Value	Source
1,7-Dimethylate	Generator
1,7-Dimethylic acid	Generator
1,7-Dimethylurate	HMDB
7,9-Dihydro-1,7-dimethyl-1H-purine-2,6,8(3H)-trione	HMDB
1,7-Dimethyluric acid	HMDB

Molecular Formula

C₇H₈N₄O₃

Average Mass

196.1634

Monoisotopic Mass

196.059640142

IUPAC Name

2,8-dihydroxy-1,7-dimethyl-6,7-dihydro-1H-purin-6-one

Traditional Name

1,7-dimethyluric acid

CAS Registry Number

Not Available

SMILES

CN1C(=O)NC2=C1C(=O)N(C)C(=O)N2

InChI Identifier

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

InChI Key

NOFNCLGCUJJPKU-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
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:68449 )
Purine alkaloids (C16356 )
a small molecule (CPD-12483 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	8.49 g/L	ALOGPS
logP	-0.81	ALOGPS
logP	0.47	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.95 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	48.92 m³·mol⁻¹	ChemAxon
Polarizability	18.06 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-029l-0900000000-fa683b3e4ecb7c70f206	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0002-0900000000-ae0b921d4ce14cd8443d	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-001i-0900000000-9d422231f3b705d6e815	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9700000000-6491a6bc04a43c894cb9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-dc89f209b88b1ac67174	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-675b5fdafca001d80248	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001r-1900000000-c2d5c6abe6b39584b025	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000t-0900000000-c0656b4118f8e8d70f7f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-000l-3900000000-d0532c0da4f328ec628e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9600000000-0a0b1bbeea391a74863f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-e7dcbea73875e9e0e50e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0900000000-f40482c57d127e32f8e4	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-0007-0900000000-6860551c1745ba41864f	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-0002-0900000000-c180cf8aed0912f88a75	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0002-0900000000-440ffa8e3cca49f55cc5	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0002-0900000000-9191d6a6a1abdd23d811	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0002-0900000000-1b5e888daf17a0165e55	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0005-0900000000-df2cb96313fe3610cc44	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0007-0900000000-6234b012018c1ae4d86e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-0006-1900000000-86334014f96303c72304	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-0006-6900000000-ca9b5373df8e0ea8fcd3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-01bc-9300000000-7a850dc063e0bf5fd5fb	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 13V, positive	splash10-0006-0900000000-0277172e5e710f4775de	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 13V, positive	splash10-03di-6900000000-542cf592e0459e911f5c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 13V, positive	splash10-00xr-9000000000-db67735b192b87b601b3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 13V, positive	splash10-000i-0900000000-e0b8225c7958cf0367cf	2020-07-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Kidney
Liver
Urine

Tissue Locations

Kidney
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191852	Xanthine dehydrogenase/oxidase	Unknown	P47989	Homo sapiens
MMDBp0193115	Cytochrome P450 1A2	Unknown	P05177	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Asthma	Slight Increase	Association	Human Urine	HMDB	15537072

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	3	Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	20.0	5.7	32.0	umol/mmol creatinine	Adult (>18 years old)	Both	Asthma	HMDB	15537072
Human Urine	Detected and Quantified	3.0	2.38	6.7	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15537072
Human Kidney	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	19754154
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24801555
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25762808
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0011103

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027886

KNApSAcK ID

Not Available

Chemspider ID

82720

KEGG Compound ID

C16356

BioCyc ID

CPD-12483

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91611

PDB ID

Not Available

ChEBI ID

68449

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sinues B, Fanlo A, Mayayo E, Carcas C, Vicente J, Arenaz I, Cebollada A: CYP2A6 activity in a healthy Spanish population: effect of age, sex, smoking, and oral contraceptives. Hum Exp Toxicol. 2008 May;27(5):367-72. doi: 10.1177/0960327107082224. [PubMed:18715882 ]

Showing metabocard for 1,7-Dimethyluric acid (MMDBc0000443)

MOL for #<Metabolite:0x00007fd10c2c7808>

3D MOL for #<Metabolite:0x00007fd10c2c7808>

3D SDF for #<Metabolite:0x00007fd10c2c7808>

3D-SDF for #<Metabolite:0x00007fd10c2c7808>

PDB for #<Metabolite:0x00007fd10c2c7808>

3D PDB for #<Metabolite:0x00007fd10c2c7808>

SMILES for #<Metabolite:0x00007fd10c2c7808>

INCHI for #<Metabolite:0x00007fd10c2c7808>

Structure for #<Metabolite:0x00007fd10c2c7808>

3D Structure for #<Metabolite:0x00007fd10c2c7808>