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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2008-10-16 22:20:23 UTC

Update Date

2023-02-21 17:17:26 UTC

HMDB ID

HMDB0010738

Secondary Accession Numbers

HMDB10738

Metabolite Identification

Common Name

1-Methylxanthine

Description

1-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. 1-Methylxanthine exists in all living organisms, ranging from bacteria to humans. In humans, 1-methylxanthine is involved in the caffeine metabolism pathway. 1-Methylxanthine has been detected, but not quantified in, several different foods, such as garden tomatoes (Solanum lycopersicum), lotus (Nelumbo), okras (Abelmoschus esculentus), tamarinds (Tamarindus indica), and chestnuts (Castanea). This could make 1-methylxanthine a potential biomarker for the consumption of these foods. 1-Methylxanthine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 1-Methylxanthine.

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

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

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

Traditional Name

1-methylxanthine

CAS Registry Number

6136-37-4

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 )

Ontology

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	5340 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	124.233	30932474
[M-H]-	Not Available	124.233	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000360

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.897	31661259
DarkChem	[M-H]-	133.77	31661259
DeepCCS	[M+H]+	126.836	30932474
DeepCCS	[M-H]-	123.717	30932474
DeepCCS	[M-2H]-	160.706	30932474
DeepCCS	[M+Na]+	136.104	30932474
AllCCS	[M+H]+	135.2	32859911
AllCCS	[M+H-H2O]+	130.7	32859911
AllCCS	[M+NH4]+	139.3	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.	1.98 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0537 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.56 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	99.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	478.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	325.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	64.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	202.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	47.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	273.0 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	258.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	280.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	591.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	156.8 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	685.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	197.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	258.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	668.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	256.9 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	221.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Methylxanthine	CN1C(=O)NC2=C(NC=N2)C1=O	2423.0	Standard polar	33892256
1-Methylxanthine	CN1C(=O)NC2=C(NC=N2)C1=O	2081.9	Standard non polar	33892256
1-Methylxanthine	CN1C(=O)NC2=C(NC=N2)C1=O	2150.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Methylxanthine,1TMS,isomer #1	CN1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C)C1=O	1887.5	Semi standard non polar	33892256
1-Methylxanthine,1TMS,isomer #1	CN1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C)C1=O	2085.5	Standard non polar	33892256
1-Methylxanthine,1TMS,isomer #1	CN1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C)C1=O	2822.8	Standard polar	33892256
1-Methylxanthine,1TMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C=N2	1966.8	Semi standard non polar	33892256
1-Methylxanthine,1TMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C=N2	2100.3	Standard non polar	33892256
1-Methylxanthine,1TMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C)C=N2	2699.8	Standard polar	33892256
1-Methylxanthine,2TMS,isomer #1	CN1C(=O)C2=C(N=CN2[Si](C)(C)C)N([Si](C)(C)C)C1=O	1951.8	Semi standard non polar	33892256
1-Methylxanthine,2TMS,isomer #1	CN1C(=O)C2=C(N=CN2[Si](C)(C)C)N([Si](C)(C)C)C1=O	2103.3	Standard non polar	33892256
1-Methylxanthine,2TMS,isomer #1	CN1C(=O)C2=C(N=CN2[Si](C)(C)C)N([Si](C)(C)C)C1=O	2356.5	Standard polar	33892256
1-Methylxanthine,1TBDMS,isomer #1	CN1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C(C)(C)C)C1=O	2089.4	Semi standard non polar	33892256
1-Methylxanthine,1TBDMS,isomer #1	CN1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C(C)(C)C)C1=O	2279.6	Standard non polar	33892256
1-Methylxanthine,1TBDMS,isomer #1	CN1C(=O)C2=C(N=C[NH]2)N([Si](C)(C)C(C)(C)C)C1=O	2791.5	Standard polar	33892256
1-Methylxanthine,1TBDMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C=N2	2187.1	Semi standard non polar	33892256
1-Methylxanthine,1TBDMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C=N2	2290.0	Standard non polar	33892256
1-Methylxanthine,1TBDMS,isomer #2	CN1C(=O)[NH]C2=C(C1=O)N([Si](C)(C)C(C)(C)C)C=N2	2742.7	Standard polar	33892256
1-Methylxanthine,2TBDMS,isomer #1	CN1C(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O	2364.8	Semi standard non polar	33892256
1-Methylxanthine,2TBDMS,isomer #1	CN1C(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O	2523.3	Standard non polar	33892256
1-Methylxanthine,2TBDMS,isomer #1	CN1C(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=O	2461.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methylxanthine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0apr-3900000000-88bd492326591e730086	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methylxanthine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-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 - 1-Methylxanthine NA , positive-QTOF	splash10-014i-0900000000-a729acfc9694f20accb0	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 3V, positive-QTOF	splash10-014i-0900000000-6d707d0f8b77fb6f3fcd	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 4V, positive-QTOF	splash10-014i-0900000000-a55efb1f01a8ca4a2d95	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 4V, positive-QTOF	splash10-02t9-0900000000-858059d2d9ee8414cafd	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 5V, positive-QTOF	splash10-02t9-0900000000-63a50718538a27464c46	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 6V, positive-QTOF	splash10-03di-0900000000-a00013c8cdc36103e8a3	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 8V, positive-QTOF	splash10-03di-2900000000-77efece85a8e1b602d5c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 9V, positive-QTOF	splash10-08fr-6900000000-0d9cd06c582f1bf23225	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 11V, positive-QTOF	splash10-0a4i-9300000000-b73bf7301278872b9e26	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 14V, positive-QTOF	splash10-0a4i-9100000000-c05924743c475bbab05b	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 17V, positive-QTOF	splash10-0a4i-9000000000-c01a620479ccd936f5ea	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine n/a 11V, positive-QTOF	splash10-03di-0900000000-9fadde7724e8a2f4bab8	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine n/a 11V, positive-QTOF	splash10-001i-9000000000-5277d916d914013bd114	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine n/a 11V, positive-QTOF	splash10-00di-0900000000-b32aa806de261f5c0e40	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 2V, positive-QTOF	splash10-03di-1900000000-14f01d07c28c61c92026	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 2V, positive-QTOF	splash10-03di-1900000000-56b961120be01ee88794	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 3V, positive-QTOF	splash10-03di-2900000000-a21b7d715ff67be12f30	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 4V, positive-QTOF	splash10-03di-5900000000-f069376ed73a3dc10f54	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methylxanthine Orbitrap 5V, positive-QTOF	splash10-0bt9-9500000000-627f0d2416135b20579b	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylxanthine 10V, Positive-QTOF	splash10-014i-0900000000-870901373643f9963bf5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylxanthine 20V, Positive-QTOF	splash10-03xr-0900000000-54540cdf9de1abed31f9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylxanthine 40V, Positive-QTOF	splash10-02u0-9400000000-df69b5d77ae7adac9ed5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylxanthine 10V, Negative-QTOF	splash10-014i-1900000000-f6dc4dabad421c556050	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylxanthine 20V, Negative-QTOF	splash10-014i-3900000000-82481c42feeeb1737775	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methylxanthine 40V, Negative-QTOF	splash10-05mo-9200000000-c5e7b6ee0ee1354a37ac	2015-04-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-03	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

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Caffeine Metabolism

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	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24801555	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25762808	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	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	6.0 (4.0-9.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15537072	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	6.0 (4.0-10.0) umol/mmol creatinine	Adult (>18 years old)	Both	Asthma	15537072	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] 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 ]

Associated OMIM IDs

114500 (Colorectal cancer)
600807 (Asthma)

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1155501

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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 ]

Enzymes

Enzyme Details

1. Xanthine dehydrogenase/oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:: XDH
Uniprot ID:: P47989
Molecular weight:: 146422.99

Reactions

1-Methylxanthine + Water + Oxygen → 1-Methyluric acid + Hydrogen peroxide	details

Enzyme Details

2. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

Showing metabocard for 1-Methylxanthine (HMDB0010738)

MOL for HMDB0010738 (1-Methylxanthine)

3D MOL for HMDB0010738 (1-Methylxanthine)

3D SDF for HMDB0010738 (1-Methylxanthine)

3D-SDF for HMDB0010738 (1-Methylxanthine)

PDB for HMDB0010738 (1-Methylxanthine)

3D PDB for HMDB0010738 (1-Methylxanthine)

SMILES for HMDB0010738 (1-Methylxanthine)

INCHI for HMDB0010738 (1-Methylxanthine)

Structure for HMDB0010738 (1-Methylxanthine)

3D Structure for HMDB0010738 (1-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

Enzymes

Reactions