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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-01-29 12:09:56 UTC

Update Date

2023-02-21 17:17:28 UTC

HMDB ID

HMDB0011599

Secondary Accession Numbers

HMDB11599

Metabolite Identification

Common Name

1-Methyladenine

Description

1-Methyladenine belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 1-Methyladenine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 1-methyladenine a potential biomarker for the consumption of these foods. 1-Methyladenine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 1-Methyladenine, with regard to humans, has been linked to the inborn metabolic disorder adenosine deaminase deficiency. Based on a literature review a significant number of articles have been published on 1-Methyladenine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N1-Methyladenine	ChEBI
1, 9-dihydro-1-Methyl-6H-purin-6-imine	HMDB
1-Methyl-1H-purin-6-amine	HMDB
1-Methyl-1H-purin-6-ylamine	HMDB
1-Methyl-adenine	HMDB

Chemical Formula

C₆H₇N₅

Average Molecular Weight

149.1533

Monoisotopic Molecular Weight

149.070145249

IUPAC Name

1-methyl-1H-purin-6-amine

Traditional Name

1-methyl-1H-purin-6-amine

CAS Registry Number

5142-22-3

SMILES

CN1C=NC2=NC=NC2=C1N

InChI Identifier

InChI=1S/C6H7N5/c1-11-3-10-6-4(5(11)7)8-2-9-6/h2-3H,7H2,1H3

InChI Key

HPZMWTNATZPBIH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

6-aminopurines

Alternative Parents

Substituents

6-aminopurine
Aminopyrimidine
Pyrimidine
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyladenine (CHEBI:18083 )
a small molecule (1-METHYLADENINE )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	> 300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	130.967	30932474
[M+H]+	Baker	128.353	30932474
[M-H]-	Not Available	130.967	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001787
[M+H]+	Not Available	128.353	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001787

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.91 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-0.5	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.62 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.81 m³·mol⁻¹	ChemAxon
Polarizability	14.43 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]+	128.988	31661259
DarkChem	[M-H]-	128.229	31661259
DeepCCS	[M+H]+	129.233	30932474
DeepCCS	[M-H]-	126.885	30932474
DeepCCS	[M-2H]-	162.865	30932474
DeepCCS	[M+Na]+	137.575	30932474
AllCCS	[M+H]+	132.3	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	136.6	32859911
AllCCS	[M+Na]+	137.9	32859911
AllCCS	[M-H]-	128.5	32859911
AllCCS	[M+Na-2H]-	129.5	32859911
AllCCS	[M+HCOO]-	130.7	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.	1.78 minutes	32390414
Predicted by Siyang on May 30, 2022	8.119 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.15 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	104.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	542.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	298.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	51.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	197.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	76.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	256.2 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	228.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	440.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	536.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	44.0 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	556.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	200.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	501.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	537.2 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	146.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Methyladenine	CN1C=NC2=NC=NC2=C1N	2399.4	Standard polar	33892256
1-Methyladenine	CN1C=NC2=NC=NC2=C1N	1620.0	Standard non polar	33892256
1-Methyladenine	CN1C=NC2=NC=NC2=C1N	1932.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Methyladenine,1TMS,isomer #1	CN1C=NC2=NC=NC2=C1N[Si](C)(C)C	2022.7	Semi standard non polar	33892256
1-Methyladenine,1TMS,isomer #1	CN1C=NC2=NC=NC2=C1N[Si](C)(C)C	1830.9	Standard non polar	33892256
1-Methyladenine,1TMS,isomer #1	CN1C=NC2=NC=NC2=C1N[Si](C)(C)C	2825.7	Standard polar	33892256
1-Methyladenine,2TMS,isomer #1	CN1C=NC2=NC=NC2=C1N([Si](C)(C)C)[Si](C)(C)C	1892.5	Semi standard non polar	33892256
1-Methyladenine,2TMS,isomer #1	CN1C=NC2=NC=NC2=C1N([Si](C)(C)C)[Si](C)(C)C	1915.7	Standard non polar	33892256
1-Methyladenine,2TMS,isomer #1	CN1C=NC2=NC=NC2=C1N([Si](C)(C)C)[Si](C)(C)C	2492.0	Standard polar	33892256
1-Methyladenine,1TBDMS,isomer #1	CN1C=NC2=NC=NC2=C1N[Si](C)(C)C(C)(C)C	2242.9	Semi standard non polar	33892256
1-Methyladenine,1TBDMS,isomer #1	CN1C=NC2=NC=NC2=C1N[Si](C)(C)C(C)(C)C	2024.9	Standard non polar	33892256
1-Methyladenine,1TBDMS,isomer #1	CN1C=NC2=NC=NC2=C1N[Si](C)(C)C(C)(C)C	2892.2	Standard polar	33892256
1-Methyladenine,2TBDMS,isomer #1	CN1C=NC2=NC=NC2=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2295.2	Semi standard non polar	33892256
1-Methyladenine,2TBDMS,isomer #1	CN1C=NC2=NC=NC2=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2333.7	Standard non polar	33892256
1-Methyladenine,2TBDMS,isomer #1	CN1C=NC2=NC=NC2=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2587.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyladenine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-4900000000-f072057fd2e79f405bb4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyladenine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 10V, Positive-QTOF	splash10-0udi-0900000000-5c8b7b78cfeaed480069	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 20V, Positive-QTOF	splash10-0udi-0900000000-43ecee09f3839868d64a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 40V, Positive-QTOF	splash10-05fu-9500000000-25484796e09297895532	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 10V, Negative-QTOF	splash10-0002-0900000000-481001363707d4d47225	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 20V, Negative-QTOF	splash10-0002-1900000000-527244488c433cfa02fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 40V, Negative-QTOF	splash10-0a6r-8900000000-69922974e3706889c4e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 10V, Positive-QTOF	splash10-0udi-0900000000-18eefbc35459f26a6570	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 20V, Positive-QTOF	splash10-0udi-0900000000-08f7fc5284c095870791	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 40V, Positive-QTOF	splash10-05mo-9500000000-fd2c2110ae89bb30148c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 10V, Negative-QTOF	splash10-0002-0900000000-0fdae69660ea9759916e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 20V, Negative-QTOF	splash10-0002-1900000000-dfd1a46d01dc7bda7e56	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenine 40V, Negative-QTOF	splash10-0536-9600000000-f6310b9904ad41cab6ee	2021-09-23	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
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, H₂O, experimental)	2012-12-05	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

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.1 (0.0-0.20) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2597438	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	3.15 umol/mmol creatinine	Adult (>18 years old)	Female	Adenosine deaminase(ADA) deficiency	2597438	details

Associated Disorders and Diseases

Disease References

Adenosine deaminase deficiency
Mills GC: 1-Methyladenine in urine of an adenosine deaminase-deficient adult without immunodeficiency. Biochem Med Metab Biol. 1989 Dec;42(3):240-7. [PubMed:2597438 ]

Associated OMIM IDs

102700 (Adenosine deaminase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028310

KNApSAcK ID

Not Available

Chemspider ID

71157

KEGG Compound ID

C02216

BioCyc ID

1-METHYLADENINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78821

PDB ID

Not Available

ChEBI ID

18083

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000843

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Falnes PO: Repair of 3-methylthymine and 1-methylguanine lesions by bacterial and human AlkB proteins. Nucleic Acids Res. 2004 Dec 1;32(21):6260-7. Print 2004. [PubMed:15576352 ]

Showing metabocard for 1-Methyladenine (HMDB0011599)

MOL for HMDB0011599 (1-Methyladenine)

3D MOL for HMDB0011599 (1-Methyladenine)

3D SDF for HMDB0011599 (1-Methyladenine)

3D-SDF for HMDB0011599 (1-Methyladenine)

PDB for HMDB0011599 (1-Methyladenine)

3D PDB for HMDB0011599 (1-Methyladenine)

SMILES for HMDB0011599 (1-Methyladenine)

INCHI for HMDB0011599 (1-Methyladenine)

Structure for HMDB0011599 (1-Methyladenine)

3D Structure for HMDB0011599 (1-Methyladenine)

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