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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-02-28 10:47:30 UTC

Update Date

2023-02-21 17:15:55 UTC

HMDB ID

HMDB0001886

Secondary Accession Numbers

HMDB01886

Metabolite Identification

Common Name

3-Methylxanthine

Description

3-methyl-9H-xanthine is a 3-methylxanthine tautomer where the imidazole proton is located at the 9-position. It has a role as a metabolite. It is a tautomer of a 3-methyl-7H-xanthine. 3-Methylxanthine, also known as 3 MX or purine analog, 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.

Structure

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

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      29.132 -10.113   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      31.800  -5.493   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      31.800 -10.113   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      30.466  -7.803   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      34.590  -7.333   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      34.590  -9.812   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      31.800 -11.653   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.466  -9.343   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.800  -7.033   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.133  -9.343   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.133  -7.803   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.489  -8.573   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    7    8   10                                                  
CONECT    4    8    9                                                       
CONECT    5   11   12                                                       
CONECT    6   10   12                                                       
CONECT    7    3                                                            
CONECT    8    1    3    4                                                  
CONECT    9    2    4   11                                                  
CONECT   10    3    6   11                                                  
CONECT   11    5    9   10                                                  
CONECT   12    5    6                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-oxo-3-Methylhypoxanthine	ChEBI
3 MX	ChEBI
3,9-Dihydro-3-methyl-1H-purine-2,6-dione	ChEBI
3-Methyl-3,7(9)-dihydro-purine-2,6-dione	ChEBI
3-Methyl-3,9-dihydro-2H,6H-purine-2,6-dione	ChEBI
3-Methylxanthine, methyl-(13)C-labeled	MeSH
3-Methylxanthine, monopotassium salt	MeSH
3-Methylxanthine, monosodium salt	MeSH
2,6-Dihydroxy-3-methylpurine	HMDB
3-Methyl xanthine	HMDB
3-Methyl-3,9-dihydro-purine-2,6-dione	HMDB
Purine analog	HMDB
3-Methylxanthine	ChEBI

Chemical Formula

C₆H₆N₄O₂

Average Molecular Weight

166.1374

Monoisotopic Molecular Weight

166.049075456

IUPAC Name

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

Traditional Name

3-methylxanthine

CAS Registry Number

1076-22-8

SMILES

CN1C2=C(NC=N2)C(=O)NC1=O

InChI Identifier

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

InChI Key

GMSNIKWWOQHZGF-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
Purinone
Alkaloid or derivatives
Pyrimidone
Hydroxypyrimidine
Pyrimidine
Heteroaromatic compound
Imidazole
Azole
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

3-methylxanthine (CHEBI:62207 )
Purine alkaloids (C16357 )
a small molecule (3-METHYLXANTHINE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Liver (HMDB: HMDB0001886)
Kidney (HMDB: HMDB0001886)

Excreta

Biofluid or Excreta

Urine (PMID: 15537072)
Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0001886)

Source

Endogenous

Endogenous (HMDB: HMDB0001886)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0001886)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0001886)

Tea

Tea products (HMDB: HMDB0001886)

Process

Naturally occurring process

Biological process

Biochemical pathway

Asthma (HMDB: HMDB0001886)

Role

Biological role

Drug metabolite (HMDB: HMDB0001886)

Industrial application

Pharmaceutical industry

Biomarker

Asthma (MarkerDB: MDB00029999)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	> 300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	8394 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.50	GASPARI,F & BONATI,M (1987)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	124.484	30932474
[M-H]-	Not Available	124.484	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000346
[M+H]+	Not Available	127.896	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000346

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.7 g/L	ALOGPS
logP	-0.46	ALOGPS
logP	-0.99	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.09 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.04 m³·mol⁻¹	ChemAxon
Polarizability	14.75 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]+	134.204	31661259
DarkChem	[M-H]-	133.323	31661259
AllCCS	[M+H]+	135.203	32859911
AllCCS	[M-H]-	130.556	32859911
DeepCCS	[M+H]+	124.717	30932474
DeepCCS	[M-H]-	121.002	30932474
DeepCCS	[M-2H]-	158.764	30932474
DeepCCS	[M+Na]+	134.303	30932474
AllCCS	[M+H]+	135.2	32859911
AllCCS	[M+H-H2O]+	130.7	32859911
AllCCS	[M+NH4]+	139.4	32859911
AllCCS	[M+Na]+	140.6	32859911
AllCCS	[M-H]-	130.6	32859911
AllCCS	[M+Na-2H]-	131.3	32859911
AllCCS	[M+HCOO]-	132.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.05 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0928 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.54 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	64.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	578.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	318.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	70.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	203.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	52.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	274.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	260.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	127.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	598.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	250.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	704.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	654.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	225.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	197.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methylxanthine	CN1C2=C(NC=N2)C(=O)NC1=O	2578.8	Standard polar	33892256
3-Methylxanthine	CN1C2=C(NC=N2)C(=O)NC1=O	1950.5	Standard non polar	33892256
3-Methylxanthine	CN1C2=C(NC=N2)C(=O)NC1=O	2122.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methylxanthine,1TMS,isomer #1	CN1C(=O)[NH]C(=O)C2=C1N=CN2[Si](C)(C)C	1962.7	Semi standard non polar	33892256
3-Methylxanthine,1TMS,isomer #1	CN1C(=O)[NH]C(=O)C2=C1N=CN2[Si](C)(C)C	2067.7	Standard non polar	33892256
3-Methylxanthine,1TMS,isomer #1	CN1C(=O)[NH]C(=O)C2=C1N=CN2[Si](C)(C)C	2676.8	Standard polar	33892256
3-Methylxanthine,1TMS,isomer #2	CN1C(=O)N([Si](C)(C)C)C(=O)C2=C1N=C[NH]2	1922.3	Semi standard non polar	33892256
3-Methylxanthine,1TMS,isomer #2	CN1C(=O)N([Si](C)(C)C)C(=O)C2=C1N=C[NH]2	2078.2	Standard non polar	33892256
3-Methylxanthine,1TMS,isomer #2	CN1C(=O)N([Si](C)(C)C)C(=O)C2=C1N=C[NH]2	2827.5	Standard polar	33892256
3-Methylxanthine,2TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C(=O)C2=C1N=CN2[Si](C)(C)C	1969.2	Semi standard non polar	33892256
3-Methylxanthine,2TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C(=O)C2=C1N=CN2[Si](C)(C)C	2089.9	Standard non polar	33892256
3-Methylxanthine,2TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C(=O)C2=C1N=CN2[Si](C)(C)C	2372.5	Standard polar	33892256
3-Methylxanthine,1TBDMS,isomer #1	CN1C(=O)[NH]C(=O)C2=C1N=CN2[Si](C)(C)C(C)(C)C	2183.2	Semi standard non polar	33892256
3-Methylxanthine,1TBDMS,isomer #1	CN1C(=O)[NH]C(=O)C2=C1N=CN2[Si](C)(C)C(C)(C)C	2253.4	Standard non polar	33892256
3-Methylxanthine,1TBDMS,isomer #1	CN1C(=O)[NH]C(=O)C2=C1N=CN2[Si](C)(C)C(C)(C)C	2716.8	Standard polar	33892256
3-Methylxanthine,1TBDMS,isomer #2	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1N=C[NH]2	2127.9	Semi standard non polar	33892256
3-Methylxanthine,1TBDMS,isomer #2	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1N=C[NH]2	2254.9	Standard non polar	33892256
3-Methylxanthine,1TBDMS,isomer #2	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1N=C[NH]2	2807.4	Standard polar	33892256
3-Methylxanthine,2TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1N=CN2[Si](C)(C)C(C)(C)C	2357.5	Semi standard non polar	33892256
3-Methylxanthine,2TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1N=CN2[Si](C)(C)C(C)(C)C	2508.0	Standard non polar	33892256
3-Methylxanthine,2TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1N=CN2[Si](C)(C)C(C)(C)C	2488.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylxanthine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01bj-5900000000-e52c5f846a0fa5fe07ef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-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 - 3-Methylxanthine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-1900000000-ddc5f6a902d7bbd1fb47	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-01b9-1900000000-c8fefaf49ff542098257	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9100000000-e21e77b88dfb9995efdd	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-014i-1900000000-e5e3ab4240496c2d1174	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-014i-0900000000-18cbc6f55db32d03e9fb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine LC-ESI-QTOF , negative-QTOF	splash10-014i-0900000000-18cbc6f55db32d03e9fb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine LC-ESI-QTOF , positive-QTOF	splash10-014i-1900000000-e5e3ab4240496c2d1174	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine 40V, Positive-QTOF	splash10-00kf-9000000000-2798f94f3fae6b71fd24	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine 10V, Negative-QTOF	splash10-014i-1900000000-e669f6d72e0c6f52426d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine 20V, Positive-QTOF	splash10-00xr-4900000000-c551a8b2a18860020666	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine 10V, Positive-QTOF	splash10-014i-0900000000-368b9799295bcad108a6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine 20V, Negative-QTOF	splash10-00xu-5900000000-37aae7a39dc6fe95fe73	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine 30V, Negative-QTOF	splash10-00r6-9300000000-8446d34de983224e406e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylxanthine 40V, Negative-QTOF	splash10-014l-9000000000-e59666cd3257a8b919c2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylxanthine 10V, Positive-QTOF	splash10-014i-0900000000-c30c1961ecbdf271a24e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylxanthine 20V, Positive-QTOF	splash10-014i-1900000000-ab9e73c4012de4c80f38	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylxanthine 40V, Positive-QTOF	splash10-014i-9100000000-8c4dac19316eed77c6dc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylxanthine 10V, Negative-QTOF	splash10-014i-0900000000-ef5279264b1ae3a9f2c0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylxanthine 20V, Negative-QTOF	splash10-01bc-5900000000-ae2f574c67e566bead1c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylxanthine 40V, Negative-QTOF	splash10-0006-9100000000-1a0783c7fb8ec28a786f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylxanthine 10V, Positive-QTOF	splash10-014i-0900000000-d3632c2d43dc7c3c5d2b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylxanthine 20V, Positive-QTOF	splash10-014i-4900000000-c71fccea6e32b15af7fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylxanthine 40V, Positive-QTOF	splash10-00kf-9200000000-9a5e9e09ea4184c6ef37	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylxanthine 10V, Negative-QTOF	splash10-014i-0900000000-d5b4655ae02ddbadcfc0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylxanthine 20V, Negative-QTOF	splash10-014i-4900000000-21e34d3a8183ecf2d209	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	4.0 (2.3-6.3) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15537072	details
Urine	Detected and Quantified	4.73 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Shaykhutdinov RA,...	details
Urine	Detected and Quantified	6.2 (1.4-17.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	10.322 +/- 9.229 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19754154	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	8.0 (5.0-14.0) umol/mmol creatinine	Adult (>18 years old)	Both	Asthma	15537072	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	21389975	details
Urine	Detected and Quantified	12.755 +/- 12.241 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Asthma
Zydron M, Baranowski J, Baranowska I: Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. J Sep Sci. 2004 Oct;27(14):1166-72. [PubMed:15537072 ]
Autosomal dominant polycystic kidney disease
Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
600807 (Asthma)
601313 (Autosomal dominant polycystic kidney disease)
610247 (Eosinophilic esophagitis)

External Links

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

2820

PubChem Compound

70639

PDB ID

Not Available

ChEBI ID

62207

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029999

Good Scents ID

rw1192211

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Orlando R, Padrini R, Perazzi M, De Martin S, Piccoli P, Palatini P: Liver dysfunction markedly decreases the inhibition of cytochrome P450 1A2-mediated theophylline metabolism by fluvoxamine. Clin Pharmacol Ther. 2006 May;79(5):489-99. [PubMed:16678550 ]
Knoppert DC, Spino M, Beck R, Thiessen JJ, MacLeod SM: Cystic fibrosis: enhanced theophylline metabolism may be linked to the disease. Clin Pharmacol Ther. 1988 Sep;44(3):254-64. [PubMed:3046811 ]
Miller M, Opheim KE, Raisys VA, Motulsky AG: Theophylline metabolism: variation and genetics. Clin Pharmacol Ther. 1984 Feb;35(2):170-82. [PubMed:6362955 ]
Desiraju RK, Sugita ET, Mayock RL: Determination of theophylline and its metabolites by liquid chromatography. J Chromatogr Sci. 1977 Dec;15(12):563-8. [PubMed:591601 ]
Tarka SM Jr, Arnaud MJ, Dvorchik BH, Vesell ES: Theobromine kinetics and metabolic disposition. Clin Pharmacol Ther. 1983 Oct;34(4):546-55. [PubMed:6617078 ]
Tateishi T, Asoh M, Yamaguchi A, Yoda T, Okano YJ, Koitabashi Y, Kobayashi S: Developmental changes in urinary elimination of theophylline and its metabolites in pediatric patients. Pediatr Res. 1999 Jan;45(1):66-70. [PubMed:9890610 ]
Geraets L, Moonen HJ, Wouters EF, Bast A, Hageman GJ: Caffeine metabolites are inhibitors of the nuclear enzyme poly(ADP-ribose)polymerase-1 at physiological concentrations. Biochem Pharmacol. 2006 Sep 28;72(7):902-10. Epub 2006 Jul 25. [PubMed:16870158 ]

Showing metabocard for 3-Methylxanthine (HMDB0001886)

MOL for HMDB0001886 (3-Methylxanthine)

3D MOL for HMDB0001886 (3-Methylxanthine)

3D SDF for HMDB0001886 (3-Methylxanthine)

3D-SDF for HMDB0001886 (3-Methylxanthine)

PDB for HMDB0001886 (3-Methylxanthine)

3D PDB for HMDB0001886 (3-Methylxanthine)

SMILES for HMDB0001886 (3-Methylxanthine)

INCHI for HMDB0001886 (3-Methylxanthine)

Structure for HMDB0001886 (3-Methylxanthine)

3D Structure for HMDB0001886 (3-Methylxanthine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra