MiMeDB: Showing metabocard for 7-Methylguanine (MMDBc0000377)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:26 UTC

Update Date

2024-04-30 19:32:00 UTC

Metabolite ID

MMDBc0000377

Metabolite Identification

Common Name

7-Methylguanine

Description

7-Methylguanine is a metabolite of DNA methylation and depurination observed in normal human biofluids; however, it has been found significantly higher in the urine of smokers than in nonsmokers. (PMID 16059882 ). 7-Methylguanine has been identified in the human placenta (PMID: 32033212 ).

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      23.403  -3.969   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      23.403  -5.509   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      26.195  -5.812   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      24.740  -6.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.095  -7.049   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.674  -4.347   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      23.403  -8.594   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      24.740  -7.821   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.065  -7.821   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      26.195  -8.295   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      22.065  -6.281   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      20.738  -8.589   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1   11    4                                                  
CONECT    3    4    5    6                                                  
CONECT    4    3    8    2                                                  
CONECT    5    3   10                                                       
CONECT    6    3                                                            
CONECT    7    8    9                                                       
CONECT    8    7   10    4                                                  
CONECT    9    7   11   12                                                  
CONECT   10    8    5                                                       
CONECT   11    2    9                                                       
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

Synonyms

Value	Source
2-Amino-1,7-dihydro-7-methyl-6H-purin-6-one	ChEBI
2-Amino-7-methylhypoxanthine	ChEBI
N(7)-Methylguanine	ChEBI
2-Amino-1,7-dihydroxy-7-methyl-6H-purine-6-one	HMDB
2-Amino-6-hydroxy-7-methylpurine	HMDB
7-Methyl-guanine	HMDB
7-Methyl-guanine (8ci)	HMDB
N-Methylguanine	HMDB
N7-Methylguanine	HMDB
7-Methylguanine, 14C-labeled	HMDB
N2-Methylguanine	HMDB
N7-Me-g	HMDB
N(2)-Methylguanine	HMDB
7-Methylguanine	ChEBI

Molecular Formula

C₆H₇N₅O

Average Mass

165.1527

Monoisotopic Mass

165.065059871

IUPAC Name

2-amino-7-methyl-6,7-dihydro-3H-purin-6-one

Traditional Name

2-amino-7-methylhypoxanthine

CAS Registry Number

Not Available

SMILES

CN1C=NC2=C1C(=O)N=C(N)N2

InChI Identifier

InChI=1S/C6H7N5O/c1-11-2-8-4-3(11)5(12)10-6(7)9-4/h2H,1H3,(H3,7,9,10,12)

InChI Key

FZWGECJQACGGTI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. 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

Hypoxanthines

Alternative Parents

Substituents

6-oxopurine
Hypoxanthine
Aminopyrimidine
Pyrimidone
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Azacycle
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Amine
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-methylguanine (CHEBI:28664 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.12 g/L	ALOGPS
logP	-0.62	ALOGPS
logP	-0.37	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.35	ChemAxon
pKa (Strongest Basic)	2.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.8 m³·mol⁻¹	ChemAxon
Polarizability	15.41 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01bi-2900000000-b0a95cd14f249c667450	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0900000000-9467edfe6e5fe41d80c7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-0900000000-248230263bb02a17634d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-64ba12b6ac3ae920980e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0900000000-6d69b62500523e3dc3d0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-0900000000-37d2717efb3cfd99a3a5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-1900000000-9b6a6193e87ed7391bfd	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-2900000000-8bc29ce14fc996e59b37	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-6900000000-b9b860095178bfbd4cd4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00kb-1900000000-0d0f6cc2cd44562b2323	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-9500000000-80f25018b3b2b6146ab0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-9600000000-ab600e6988ac4e56e321	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00dj-9400000000-e929965f6c63f59fcb15	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014j-9000000000-fa82f4a1c9751a539c26	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0900000000-6d69b62500523e3dc3d0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0900000000-2105f1b548050728fb41	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-1900000000-9b6a6193e87ed7391bfd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-2900000000-8bc29ce14fc996e59b37	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-6900000000-b9b860095178bfbd4cd4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00kb-1900000000-61125a8802327f88d32a	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-7bbf7f0a999ef7bf8afb	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-b6a2ab544a0f5c16da9b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-9800000000-eee86daa744a6ab97786	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-8ba30384438f851de3ff	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1900000000-f0d2b014e6cd3c2588c4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9100000000-6fba35b30d5f7e144718	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Leukocyte
Placenta

Tissue Locations

Leukocyte
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193695	DNA-3-methyladenine glycosylase	Enzyme	P29372	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	1	Human feces; Human stool; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	7	Human stool; Human ; Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.129	0.024	uM	Adult (>18 years old)	Both	Normal	HMDB	2437827
Human Leukocyte	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000897

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022305

KNApSAcK ID

Not Available

Chemspider ID

10883

KEGG Compound ID

C02242

BioCyc ID

CPD0-2377

BiGG ID

Not Available

Wikipedia Link

7-Methylguanine

METLIN ID

Not Available

PubChem Compound

11361

PDB ID

Not Available

ChEBI ID

28664

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Mustonen R, Hemminki K: 7-Methylguanine levels in DNA of smokers' and non-smokers' total white blood cells, granulocytes and lymphocytes. Carcinogenesis. 1992 Nov;13(11):1951-5. doi: 10.1093/carcin/13.11.1951. [PubMed:1423861 ]
van Delft JH, van den Ende AM, Keizer HJ, Ouwerkerk J, Baan RA: Determination of N7-methylguanine in DNA of white blood cells from cancer patients treated with dacarbazine. Carcinogenesis. 1992 Jul;13(7):1257-9. doi: 10.1093/carcin/13.7.1257. [PubMed:1638694 ]
Kumar R, Hemminki K: Separation of 7-methyl- and 7-(2-hydroxyethyl)-guanine adducts in human DNA samples using a combination of TLC and HPLC. Carcinogenesis. 1996 Mar;17(3):485-92. doi: 10.1093/carcin/17.3.485. [PubMed:8631134 ]
Eder E: Intraindividual variations of DNA adduct levels in humans. Mutat Res. 1999 Mar 8;424(1-2):249-61. doi: 10.1016/s0027-5107(99)00023-8. [PubMed:10064865 ]
Chao MR, Wang CJ, Yang HH, Chang LW, Hu CW: Rapid and sensitive quantification of urinary N7-methylguanine by isotope-dilution liquid chromatography/electrospray ionization tandem mass spectrometry with on-line solid-phase extraction. Rapid Commun Mass Spectrom. 2005;19(17):2427-32. doi: 10.1002/rcm.2082. [PubMed:16059882 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for 7-Methylguanine (MMDBc0000377)

MOL for #<Metabolite:0x00007fdafffcb598>

3D MOL for #<Metabolite:0x00007fdafffcb598>

3D SDF for #<Metabolite:0x00007fdafffcb598>

3D-SDF for #<Metabolite:0x00007fdafffcb598>

PDB for #<Metabolite:0x00007fdafffcb598>

3D PDB for #<Metabolite:0x00007fdafffcb598>

SMILES for #<Metabolite:0x00007fdafffcb598>

INCHI for #<Metabolite:0x00007fdafffcb598>

Structure for #<Metabolite:0x00007fdafffcb598>

3D Structure for #<Metabolite:0x00007fdafffcb598>