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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-01-29 15:21:03 UTC

Update Date

2023-02-21 17:17:29 UTC

HMDB ID

HMDB0011614

Secondary Accession Numbers

HMDB11614

Metabolite Identification

Common Name

7-Methyladenine

Description

7-Methyladenine is part of the base excision repair pathway. In this pathway, alkylated DNA is hydrolysed via the enzyme DNA-3-methyladenine glycosylase II (EC 3.2.2.21), releasing 3-methyladenine, 3-methylguanine, 7-methylguanine and 7-methyladenine. This enzyme is responsible for the hydrolysis of the deoxyribose N-glycosidic bond to excise 3-methyladenine, and 7-methylguanine from the damaged DNA polymer formed by alkylation lesions. Base excision repair (BER) is a cellular mechanism that repairs damaged DNA throughout the cell cycle. Repairing DNA sequence errors is necessary so that mutations are not propagated or to remove lesions that may lead to breaks in the DNA during replication. Single bases in DNA can be chemically mutated, for example by deamination or alkylation, resulting in incorrect base-pairing, and consequently, mutations in the DNA. Base excision repair involves flipping the mutated base out of the DNA helix and repairing the base alone. There are two main enzymes used, DNA glycosylases and AP endonucleases. The DNA glycosylase is used to break the beta-N glycosidic bond to create an AP site. AP endonuclease recognizes this site and nicks the damaged DNA on the 5' side (upstream) of the AP site creating a free 3'-OH. DNA polymerase, Pol I (human pol beta), extends the DNA from the free 3'-OH using its exonuclease activity to replace the nucleotide of the damaged base, as well as a few downstream, followed by sealing of the new DNA strand by DNA ligase. In mammalian cells, this is done by LigIII in complex with the scaffold protein XRCC1. Usually, BER is divided into short-patch repair (where a single nucleotide is replaced) or long-patch repair (where 2-10 nucleotides are replaced). Mammalian long-patch repair includes PCNA and pol delta/epsilon for nucleotide resynthesis, FEN1 to cut of the 'flap' including the damaged base, and LigI.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
7-Methyladenine	ChEMBL, HMDB
6-amino-7-Methylpurine	HMDB
7-Methyl-7H-purin-6-amine	HMDB
7-Methyl-7H-purin-6-amine (acd/name 4.0)	HMDB
7-Methyl-7H-purin-6-ylamine (acd/name 4.0)	HMDB
7-Methyl-N7-methyladenine	HMDB

Chemical Formula

C₆H₇N₅

Average Molecular Weight

149.1533

Monoisotopic Molecular Weight

149.070145249

IUPAC Name

7-methyl-7H-purin-6-amine

Traditional Name

7-methyladenine

CAS Registry Number

935-69-3

SMILES

CN1C=NC2=NC=NC(N)=C12

InChI Identifier

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

InChI Key

HCGHYQLFMPXSDU-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
N-substituted imidazole
Pyrimidine
Imidolactam
Azole
Imidazole
Heteroaromatic compound
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Primary amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyladenine (CHEBI:28921 )
a purine base (CPD-13320 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Endogenous

Endogenous (HMDB: HMDB0011614)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Not Available

Role

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	4.66 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	-0.35	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Basic)	3.6	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	43.12 m³·mol⁻¹	ChemAxon
Polarizability	14.29 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]+	128.984	31661259
DarkChem	[M-H]-	128.228	31661259
DeepCCS	[M-2H]-	162.672	30932474
DeepCCS	[M+Na]+	137.994	30932474
AllCCS	[M+H]+	132.4	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	136.7	32859911
AllCCS	[M+Na]+	137.9	32859911
AllCCS	[M-H]-	128.5	32859911
AllCCS	[M+Na-2H]-	129.6	32859911
AllCCS	[M+HCOO]-	130.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Methyladenine	CN1C=NC2=NC=NC(N)=C12	2337.7	Standard polar	33892256
7-Methyladenine	CN1C=NC2=NC=NC(N)=C12	1750.7	Standard non polar	33892256
7-Methyladenine	CN1C=NC2=NC=NC(N)=C12	1709.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Methyladenine,1TMS,isomer #1	CN1C=NC2=NC=NC(N[Si](C)(C)C)=C21	1903.6	Semi standard non polar	33892256
7-Methyladenine,1TMS,isomer #1	CN1C=NC2=NC=NC(N[Si](C)(C)C)=C21	1772.8	Standard non polar	33892256
7-Methyladenine,1TMS,isomer #1	CN1C=NC2=NC=NC(N[Si](C)(C)C)=C21	2766.1	Standard polar	33892256
7-Methyladenine,2TMS,isomer #1	CN1C=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C21	1865.2	Semi standard non polar	33892256
7-Methyladenine,2TMS,isomer #1	CN1C=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C21	1871.9	Standard non polar	33892256
7-Methyladenine,2TMS,isomer #1	CN1C=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C21	2446.8	Standard polar	33892256
7-Methyladenine,1TBDMS,isomer #1	CN1C=NC2=NC=NC(N[Si](C)(C)C(C)(C)C)=C21	2147.9	Semi standard non polar	33892256
7-Methyladenine,1TBDMS,isomer #1	CN1C=NC2=NC=NC(N[Si](C)(C)C(C)(C)C)=C21	1933.2	Standard non polar	33892256
7-Methyladenine,1TBDMS,isomer #1	CN1C=NC2=NC=NC(N[Si](C)(C)C(C)(C)C)=C21	2828.3	Standard polar	33892256
7-Methyladenine,2TBDMS,isomer #1	CN1C=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C21	2246.4	Semi standard non polar	33892256
7-Methyladenine,2TBDMS,isomer #1	CN1C=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C21	2277.4	Standard non polar	33892256
7-Methyladenine,2TBDMS,isomer #1	CN1C=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C21	2545.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Methyladenine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-2900000000-e8c3a67ccd8c708bcc39	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-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 - 7-Methyladenine 10V, Positive-QTOF	splash10-0udi-0900000000-4e05df90eeb217fb0543	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyladenine 20V, Positive-QTOF	splash10-0udi-0900000000-89d47c8d0ec0a29d619d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyladenine 40V, Positive-QTOF	splash10-00ea-9500000000-2f8613bd76fdc956419b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyladenine 10V, Negative-QTOF	splash10-0002-0900000000-77a0a50aa1ea18dfc624	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyladenine 20V, Negative-QTOF	splash10-0002-0900000000-9da281b20075d95cb8fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyladenine 40V, Negative-QTOF	splash10-060s-5900000000-7cb7767e9f0a843ef3f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyladenine 10V, Negative-QTOF	splash10-0002-0900000000-0fdae69660ea9759916e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyladenine 20V, Negative-QTOF	splash10-0002-0900000000-7e685a2f1c95c3ac528d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyladenine 40V, Negative-QTOF	splash10-014i-9300000000-f917c9f05153fdcd6add	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyladenine 10V, Positive-QTOF	splash10-0udi-0900000000-18eefbc35459f26a6570	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyladenine 20V, Positive-QTOF	splash10-0udi-0900000000-f25de4e35b83e75783bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyladenine 40V, Positive-QTOF	splash10-053r-9500000000-1fd51e3d79bd3456748f	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 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
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

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

FDB028319

KNApSAcK ID

Not Available

Chemspider ID

64663

KEGG Compound ID

C02241

BioCyc ID

CPD-13320

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71593

PDB ID

Not Available

ChEBI ID

28921

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)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. DNA-3-methyladenine glycosylase

General function:: Involved in catalytic activity
Specific function:: Hydrolysis of the deoxyribose N-glycosidic bond to excise 3-methyladenine, and 7-methylguanine from the damaged DNA polymer formed by alkylation lesions
Gene Name:: MPG
Uniprot ID:: P29372
Molecular weight:: 32868.4

Showing metabocard for 7-Methyladenine (HMDB0011614)

MOL for HMDB0011614 (7-Methyladenine)

3D MOL for HMDB0011614 (7-Methyladenine)

3D SDF for HMDB0011614 (7-Methyladenine)

3D-SDF for HMDB0011614 (7-Methyladenine)

PDB for HMDB0011614 (7-Methyladenine)

3D PDB for HMDB0011614 (7-Methyladenine)

SMILES for HMDB0011614 (7-Methyladenine)

INCHI for HMDB0011614 (7-Methyladenine)

Structure for HMDB0011614 (7-Methyladenine)

3D Structure for HMDB0011614 (7-Methyladenine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes