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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-01-09 12:11:22 UTC

Update Date

2023-02-21 17:29:15 UTC

HMDB ID

HMDB0059716

Secondary Accession Numbers

HMDB59716

Metabolite Identification

Common Name

9-Methylxanthine

Description

9-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. In another study, 9-Methylxanthine, as a chemical relatives of caffeine, is able to evoke contractures in mammalian heart. 9-Methylxanthine is an extremely weak basic (essentially neutral) compound (based on its pKa). 9-Methylxanthine is a diuretic agent that serves as a smooth muscle relexant and cardiac muscle and CNS stimulant. 9-Methylxanthine is found to be effective in treating apnea in preterm infants (PMID: 11686952 ). Clinically, it is employed as a bronchodilator.

Structure

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

HEADER    PROTEIN                                 09-JAN-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 9-Methylxanthine                                  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JAN-13         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  N   UNK     0       2.530   0.237   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       3.864  -2.073   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₆H₆N₄O₂

Average Molecular Weight

166.1374

Monoisotopic Molecular Weight

166.049075456

IUPAC Name

9-methyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

Traditional Name

methylxanthine

CAS Registry Number

Not Available

SMILES

CN1C=NC2=C1NC(=O)NC2=O

InChI Identifier

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

InChI Key

DHNIKYWYTSMDDA-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
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.72 g/L	ALOGPS
logP	-0.56	ALOGPS
logP	-0.023	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	0.38	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	40.51 m³·mol⁻¹	ChemAxon
Polarizability	14.81 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]+	134.743	31661259
DarkChem	[M-H]-	132.647	31661259
DeepCCS	[M+H]+	127.329	30932474
DeepCCS	[M-H]-	124.565	30932474
DeepCCS	[M-2H]-	161.331	30932474
DeepCCS	[M+Na]+	136.356	30932474
AllCCS	[M+H]+	134.3	32859911
AllCCS	[M+H-H2O]+	129.7	32859911
AllCCS	[M+NH4]+	138.5	32859911
AllCCS	[M+Na]+	139.7	32859911
AllCCS	[M-H]-	130.6	32859911
AllCCS	[M+Na-2H]-	131.3	32859911
AllCCS	[M+HCOO]-	132.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-Methylxanthine	CN1C=NC2=C1NC(=O)NC2=O	2566.9	Standard polar	33892256
9-Methylxanthine	CN1C=NC2=C1NC(=O)NC2=O	1826.3	Standard non polar	33892256
9-Methylxanthine	CN1C=NC2=C1NC(=O)NC2=O	2254.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9-Methylxanthine,1TMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O	1888.7	Semi standard non polar	33892256
9-Methylxanthine,1TMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O	2060.6	Standard non polar	33892256
9-Methylxanthine,1TMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C)C(=O)[NH]C2=O	2810.1	Standard polar	33892256
9-Methylxanthine,1TMS,isomer #2	CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O	1906.0	Semi standard non polar	33892256
9-Methylxanthine,1TMS,isomer #2	CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O	2131.9	Standard non polar	33892256
9-Methylxanthine,1TMS,isomer #2	CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C)C2=O	2836.9	Standard polar	33892256
9-Methylxanthine,2TMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	2020.4	Semi standard non polar	33892256
9-Methylxanthine,2TMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	2118.9	Standard non polar	33892256
9-Methylxanthine,2TMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=O	2400.4	Standard polar	33892256
9-Methylxanthine,1TBDMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O	2091.9	Semi standard non polar	33892256
9-Methylxanthine,1TBDMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O	2281.0	Standard non polar	33892256
9-Methylxanthine,1TBDMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)[NH]C2=O	2787.0	Standard polar	33892256
9-Methylxanthine,1TBDMS,isomer #2	CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O	2134.8	Semi standard non polar	33892256
9-Methylxanthine,1TBDMS,isomer #2	CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O	2321.8	Standard non polar	33892256
9-Methylxanthine,1TBDMS,isomer #2	CN1C=NC2=C1[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=O	2823.1	Standard polar	33892256
9-Methylxanthine,2TBDMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O	2309.3	Semi standard non polar	33892256
9-Methylxanthine,2TBDMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O	2503.3	Standard non polar	33892256
9-Methylxanthine,2TBDMS,isomer #1	CN1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=O	2491.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Methylxanthine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00rj-4900000000-14c9b93c2a0a573bb5a5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Methylxanthine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Methylxanthine 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 - 9-Methylxanthine 20V, Negative-QTOF	splash10-0006-9200000000-b6abb15ab6e35e228978	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 10V, Negative-QTOF	splash10-014i-3900000000-79a4c3d1ed77bec28013	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 30V, Negative-QTOF	splash10-0006-9000000000-2f53c894eb036b2baef6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 40V, Negative-QTOF	splash10-0006-9000000000-466822a9d8f10adc1577	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 0V, Positive-QTOF	splash10-014i-0900000000-e40bb3a6f8a43919e584	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 30V, Positive-QTOF	splash10-0006-9500000000-d153e1e54fadd31e7502	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 0V, Positive-QTOF	splash10-014i-0900000000-a8c2d37edc47b03668b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 10V, Positive-QTOF	splash10-014i-0900000000-16767a506e30f53c64cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 30V, Positive-QTOF	splash10-0fl3-9700000000-5a53919333c21ac6d010	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 10V, Positive-QTOF	splash10-014i-0900000000-f64facd72b87d9b945b3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 10V, Positive-QTOF	splash10-014i-0900000000-86e2afeaee08135cc56f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 20V, Positive-QTOF	splash10-0fk9-1900000000-e8e39324a58bcd907ad7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 40V, Positive-QTOF	splash10-0006-9000000000-56a793d03fe5f580ac84	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 9-Methylxanthine 30V, Positive-QTOF	splash10-0fl3-9500000000-7abf024fb291dbcf2b32	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methylxanthine 10V, Negative-QTOF	splash10-014i-0900000000-527a1e5ee8d3273d9ff1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methylxanthine 20V, Negative-QTOF	splash10-0006-9400000000-31977135b3d4c64c4cef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methylxanthine 40V, Negative-QTOF	splash10-0006-9100000000-d178774b5036960a191b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methylxanthine 10V, Negative-QTOF	splash10-014i-0900000000-d5b4655ae02ddbadcfc0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methylxanthine 20V, Negative-QTOF	splash10-014l-3900000000-a327a04048c667f854b6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methylxanthine 40V, Negative-QTOF	splash10-0006-9000000000-b279255d0a190f1ac3a4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methylxanthine 10V, Positive-QTOF	splash10-014i-0900000000-3641a8cdf2a03f895e62	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methylxanthine 20V, Positive-QTOF	splash10-01b9-0900000000-90b7792d6bd0a62afc72	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methylxanthine 40V, Positive-QTOF	splash10-006t-9600000000-aeed19861a80e9815e16	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methylxanthine 10V, Positive-QTOF	splash10-014i-0900000000-d3632c2d43dc7c3c5d2b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methylxanthine 20V, Positive-QTOF	splash10-014i-0900000000-4eb2c7c6361ac0aedfac	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Xanthine

METLIN ID

Not Available

PubChem Compound

70975

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Henderson-Smart DJ, Steer P: Methylxanthine treatment for apnea in preterm infants. Cochrane Database Syst Rev. 2001;(3):CD000140. [PubMed:11686952 ]
Chapman RA, Leoty C: Which of caffeine's chemical relatives are able to evoke contractures in mammalian heart? Recent Adv Stud Cardiac Struct Metab. 1975;7:425-30. [PubMed:1226453 ]

Showing metabocard for 9-Methylxanthine (HMDB0059716)

MOL for HMDB0059716 (9-Methylxanthine)

3D MOL for HMDB0059716 (9-Methylxanthine)

3D SDF for HMDB0059716 (9-Methylxanthine)

3D-SDF for HMDB0059716 (9-Methylxanthine)

PDB for HMDB0059716 (9-Methylxanthine)

3D PDB for HMDB0059716 (9-Methylxanthine)

SMILES for HMDB0059716 (9-Methylxanthine)

INCHI for HMDB0059716 (9-Methylxanthine)

Structure for HMDB0059716 (9-Methylxanthine)

3D Structure for HMDB0059716 (9-Methylxanthine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra