MiMeDB: Showing metabocard for 7-Methylxanthine (MMDBc0000399)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:53 UTC

Update Date

2024-04-30 19:32:09 UTC

Metabolite ID

MMDBc0000399

Metabolite Identification

Common Name

7-Methylxanthine

Description

7-Methylxanthine is a methyl derivative of xanthine, found occasionally in human urine. 7-Methylxanthine is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites, including 7-methylxanthine. 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. 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. (PMID:11712316 , 15833286 , 3506820 , 15013152 ).

Structure

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

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   1.408   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+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  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       3.864  -0.533   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.198  -2.843   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       2.530  -2.843   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

Synonyms

Value	Source
3,7-Dihydro-7-methyl-1H-purine-2,6-dione	ChEBI
7-Methylxanthin	ChEBI
Heteroxanthin	ChEBI
Heteroxanthine	ChEBI
7-Methylxanthine, 7-(13)C-labeled	MeSH
2,6-Dihydroxy-7-methylpurine	HMDB
7-Methyl-3,7-dihydro-1H-purine-2,6-dione	HMDB
7-Methyl-7H-purine-2,6-diol	HMDB
Methylxanthine	HMDB

Molecular Formula

C₆H₆N₄O₂

Average Mass

166.1374

Monoisotopic Mass

166.049075456

IUPAC Name

7-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Traditional Name

7-methylxanthine

CAS Registry Number

Not Available

SMILES

CN1C=NC2=C1C(=O)NC(=O)N2

InChI Identifier

InChI=1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12)

InChI Key

PFWLFWPASULGAN-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
Alkaloid or derivatives
Hydroxypyrimidine
Pyrimidine
N-substituted imidazole
Heteroaromatic compound
Imidazole
Azole
Azacycle
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:48991 )
purine alkaloid (CHEBI:48991 )
Purine alkaloids (C16353 )
a small molecule (7-METHYLXANTHINE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	7 g/L	ALOGPS
logP	-0.59	ALOGPS
logP	0.017	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-0.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.82 m³·mol⁻¹	ChemAxon
Polarizability	14.77 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00rb-4900000000-5a121544b907c24f5972	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
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-014i-0900000000-30f6b1fe21e6924b4408	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-00xr-6900000000-f5c1b1369f226330b60e	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-014i-9000000000-3b1edad37f3a300fd3b7	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-014i-0900000000-3c4effaf7fee8c2b61ea	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-014i-0900000000-e2df10d0ab191cf48ad3	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-007k-9000000000-b0fa1ce6138138a94167	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0fk9-0900000000-45a47f7201f1b1cc4c0a	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 2V, positive	splash10-004i-3900000000-6b031051442287925863	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-0059-7900000000-8472e8c51cabdb800b2b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-001i-9100000000-68f333821040ae2d706c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 12V, positive	splash10-001i-9100000000-3c01ab92dda7a36ca993	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 14V, positive	splash10-001i-9100000000-92ec6b69d4cfe4cd2a3d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 16V, positive	splash10-001i-9200000000-1a9b42f2cd8d64ed5d47	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 18V, positive	splash10-001i-9000000000-e26454dd03e8fe73c4a8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 26V, positive	splash10-001i-9000000000-9e6003927514a8801358	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-001i-9000000000-fa3240e26cb87ab70fa4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-001l-9000000000-9419618135a9b903f29c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-001l-9000000000-2aa69c9cec10c58e1b56	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-014i-0900000000-ce6eec4ee9efe1c5a732	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-d0d15cf114e854cb9389	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01b9-1900000000-a22c299c1d6da4639631	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kg-9200000000-5a65dfd385a5e35051c8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-1fd502b43c7af78c68ad	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9400000000-93978f7127dd2e954aa0	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-212eeb1212b80abd05eb	2017-09-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 5%_DMSO, experimental)		2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)		2012-12-05	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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	5	Human ; Human feces; Human stool; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	1	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	2	Human

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	10.0	2.7	17.8	umol/mmol creatinine	Adult (>18 years old)	Both	Asthma	HMDB	15537072
Human Urine	Detected and Quantified	10.0	6.7	14.6	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15537072
Human Urine	Detected and Quantified	10.0	3.9	16.1	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
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)	Female	Normal	HMDB	27355821
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

HMDB0001991

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Xanthine

METLIN ID

Not Available

PubChem Compound

68374

PDB ID

Not Available

ChEBI ID

48991

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1002/bmc.1130010305. [PubMed:3506820 ]
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. doi: 10.1016/S0731-7085(03)00528-4. [PubMed:15013152 ]
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. doi: 10.1016/j.jchromb.2004.11.013. [PubMed:15833286 ]

Showing metabocard for 7-Methylxanthine (MMDBc0000399)

MOL for #<Metabolite:0x00007feced82bc70>

3D MOL for #<Metabolite:0x00007feced82bc70>

3D SDF for #<Metabolite:0x00007feced82bc70>

3D-SDF for #<Metabolite:0x00007feced82bc70>

PDB for #<Metabolite:0x00007feced82bc70>

3D PDB for #<Metabolite:0x00007feced82bc70>

SMILES for #<Metabolite:0x00007feced82bc70>

INCHI for #<Metabolite:0x00007feced82bc70>

Structure for #<Metabolite:0x00007feced82bc70>

3D Structure for #<Metabolite:0x00007feced82bc70>