MiMeDB: Showing metabocard for 1-Methylxanthine (MMDBc0000442)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:51 UTC

Update Date

2024-04-30 19:32:25 UTC

Metabolite ID

MMDBc0000442

Metabolite Identification

Common Name

1-Methylxanthine

Description

1-Methylxanthine is one of the major metabolites of caffeine in humans. The oxidation of 1-methylxanthine to 1-methyluric acid occurs so rapidly that the parent compound could not be detected in plasma, and only low concentrations could be detected in the brain (PMID: 28863020 ).

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       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       2.530   4.383   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

Synonyms

Not Available

Molecular Formula

C₆H₆N₄O₂

Average Mass

166.1374

Monoisotopic Mass

166.049075456

IUPAC Name

2-hydroxy-1-methyl-6,9-dihydro-1H-purin-6-one

Traditional Name

1-methylxanthine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

MVOYJPOZRLFTCP-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

1-methylxanthine (CHEBI:68444 )
Purine alkaloids (C16358 )
a small molecule (CPD-9025 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	11.7 g/L	ALOGPS
logP	-0.46	ALOGPS
logP	-0.4	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.11	ChemAxon
pKa (Strongest Basic)	1.67	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.58 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.26 m³·mol⁻¹	ChemAxon
Polarizability	14.92 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	splash10-0apr-3900000000-88bd492326591e730086	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 - 40V, Negative	splash10-014i-9000000000-6fbdd0235ae20be5daa1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-067i-9400000000-26298794cbed4fbcad6b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-3900000000-712a7974e530515b891f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-69924d9d22c49622a32b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-014i-0900000000-a729acfc9694f20accb0	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-014i-0900000000-6d707d0f8b77fb6f3fcd	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-014i-0900000000-a55efb1f01a8ca4a2d95	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-02t9-0900000000-858059d2d9ee8414cafd	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-02t9-0900000000-63a50718538a27464c46	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-03di-0900000000-a00013c8cdc36103e8a3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-03di-2900000000-77efece85a8e1b602d5c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-08fr-6900000000-0d9cd06c582f1bf23225	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-0a4i-9300000000-b73bf7301278872b9e26	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-0a4i-9100000000-c05924743c475bbab05b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 17V, positive	splash10-0a4i-9000000000-c01a620479ccd936f5ea	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-03di-0900000000-9fadde7724e8a2f4bab8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-001i-9000000000-5277d916d914013bd114	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-00di-0900000000-b32aa806de261f5c0e40	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-03di-1900000000-14f01d07c28c61c92026	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-03di-1900000000-56b961120be01ee88794	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-03di-2900000000-a21b7d715ff67be12f30	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-03di-5900000000-f069376ed73a3dc10f54	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0bt9-9500000000-627f0d2416135b20579b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0a4i-9200000000-693e5185f1cfeede2a4f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0a4i-9000000000-3a28092a50ffbb7dd36e	2020-07-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 MHz, D₂O, predicted)		2021-09-25	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	6	Human feces; Human stool; Human ; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	1	Human feces; Human mucosa	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	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	6.0	4.0	10.0	umol/mmol creatinine	Adult (>18 years old)	Both	Asthma	HMDB	15537072
Human Urine	Detected and Quantified	6.0	4.0	9.0	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 Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24740205
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 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

HMDB0010738

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027885

KNApSAcK ID

Not Available

Chemspider ID

72464

KEGG Compound ID

C16358

BioCyc ID

CPD-9025

BiGG ID

Not Available

Wikipedia Link

Xanthine

METLIN ID

Not Available

PubChem Compound

80220

PDB ID

Not Available

ChEBI ID

68444

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sims CR 3rd, Delima LR, Calimaran A, Hester R, Pruett WA: Validating the Physiologic Model HumMod as a Substitute for Clinical Trials Involving Acute Normovolemic Hemodilution. Anesth Analg. 2018 Jan;126(1):93-101. doi: 10.1213/ANE.0000000000002430. [PubMed:28863020 ]

Showing metabocard for 1-Methylxanthine (MMDBc0000442)

MOL for #<Metabolite:0x000055e8c8d89670>

3D MOL for #<Metabolite:0x000055e8c8d89670>

3D SDF for #<Metabolite:0x000055e8c8d89670>

3D-SDF for #<Metabolite:0x000055e8c8d89670>

PDB for #<Metabolite:0x000055e8c8d89670>

3D PDB for #<Metabolite:0x000055e8c8d89670>

SMILES for #<Metabolite:0x000055e8c8d89670>

INCHI for #<Metabolite:0x000055e8c8d89670>

Structure for #<Metabolite:0x000055e8c8d89670>

3D Structure for #<Metabolite:0x000055e8c8d89670>