Bovine Metabolome Database: Showing metabocard for 7-Methylxanthine (BMDB0001991)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:49:40 UTC

Update Date

2020-05-11 20:22:59 UTC

BMDB ID

BMDB0001991

Secondary Accession Numbers

BMDB01991

Metabolite Identification

Common Name

7-Methylxanthine

Description

7-Methylxanthine, also known as 7-methylxanthine, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. 7-Methylxanthine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 7-Methylxanthine exists in all living organisms, ranging from bacteria to humans. 7-Methylxanthine participates in a number of enzymatic reactions, within cattle. In particular, 7-Methylxanthine and formaldehyde can be biosynthesized from paraxanthine; which is catalyzed by the enzyme cytochrome P450 1A2. In addition, 7-Methylxanthine can be converted into 7-methyluric acid; which is mediated by the enzyme xanthine dehydrogenase/oxidase. In cattle, 7-methylxanthineee is involved in the metabolic pathway called the caffeine metabolism pathway.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

Chemical Formula

C₆H₆N₄O₂

Average Molecular Weight

166.1374

Monoisotopic Molecular Weight

166.049075456

IUPAC Name

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

Traditional Name

7-methylxanthine

CAS Registry Number

552-62-5

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 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	> 300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-0.89	GASPARI,F & BONATI,M (1987)

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00rb-4900000000-5a121544b907c24f5972	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-014i-0900000000-30f6b1fe21e6924b4408	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-00xr-6900000000-f5c1b1369f226330b60e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-014i-9000000000-3b1edad37f3a300fd3b7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-014i-0900000000-3c4effaf7fee8c2b61ea	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-014i-0900000000-e2df10d0ab191cf48ad3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-007k-9000000000-b0fa1ce6138138a94167	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0fk9-0900000000-45a47f7201f1b1cc4c0a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 2V, positive	splash10-004i-3900000000-6b031051442287925863	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-0059-7900000000-8472e8c51cabdb800b2b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-001i-9100000000-68f333821040ae2d706c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 12V, positive	splash10-001i-9100000000-3c01ab92dda7a36ca993	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 14V, positive	splash10-001i-9100000000-92ec6b69d4cfe4cd2a3d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 16V, positive	splash10-001i-9200000000-1a9b42f2cd8d64ed5d47	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 18V, positive	splash10-001i-9000000000-e26454dd03e8fe73c4a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 26V, positive	splash10-001i-9000000000-9e6003927514a8801358	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-001i-9000000000-fa3240e26cb87ab70fa4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-001l-9000000000-9419618135a9b903f29c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-001l-9000000000-2aa69c9cec10c58e1b56	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-014i-0900000000-ce6eec4ee9efe1c5a732	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-d0d15cf114e854cb9389	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01b9-1900000000-a22c299c1d6da4639631	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kg-9200000000-5a65dfd385a5e35051c8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-1fd502b43c7af78c68ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9400000000-93978f7127dd2e954aa0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-212eeb1212b80abd05eb	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 5%_DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Kidney
Liver

Pathways

Name	SMPDB/Pathwhiz	KEGG
Caffeine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

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

References

Synthesis Reference

Hutzenlaub, Wolfgang; Pfleiderer, Wolfgang. Purines. XIII. Simplified syntheses of 7-methyl- and 1,7-dimethylxanthines and -uric acids. Liebigs Annalen der Chemie (1979), (11), 1847-54.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 7-Methylxanthine (BMDB0001991)

Structure for BMDB0001991 (7-Methylxanthine)