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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-04-12 20:56:15 UTC

Update Date

2023-02-21 17:17:13 UTC

HMDB ID

HMDB0006037

Secondary Accession Numbers

HMDB06037

Metabolite Identification

Common Name

8-Hydroxy-7-methylguanine

Description

8-Hydroxy-7-methylguanine is a modified nucleoside. 8-Hydroxy-7-methylguanine is an endogenous methylated nucleoside found in human fluids; methylated purine bases are present in higher amounts in tumor-bearing patients compared to healthy controls. Human exposure to carcinogenic alkylating agents can lead to the formation of covalently bound adducts in DNA, some of which are excreted in urine as alkylated purines following DNA degradation and repair; the N2 position of guanine is one of the major sites for DNA modification by various carcinogens. Measurements of RNA or DNA catabolites in urine can be used as a measure for the metabolism of each of the three major species of RNA. An accumulation of modified ribonucleosides appears in the serum of uremic patients. (PMID: 3506820 , 5961889 , 16527824 , 16061253 , 8043914 , 2428556 , 7159514 , 9607216 ).

Structure

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


  Mrv0541 02231220322D          

 13 14  0  0  0  0            999 V2000
   19.8406   -4.2571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0390   -5.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5341   -4.9211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5341   -3.5933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0390   -3.4322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3244   -4.6698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6099   -3.4322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7535   -4.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7535   -3.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0156   -4.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0390   -5.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7903   -5.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3244   -3.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2 11  2  0  0  0  0
  3  8  1  0  0  0  0
  3 10  1  0  0  0  0
  3 12  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5  9  1  0  0  0  0
  5 13  1  0  0  0  0
  6 11  1  0  0  0  0
  6 13  2  0  0  0  0
  7 13  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006037

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)NC2=C1C(=O)N=C(N)N2

> <INCHI_IDENTIFIER>
InChI=1S/C6H7N5O2/c1-11-2-3(9-6(11)13)8-5(7)10-4(2)12/h1H3,(H4,7,8,9,10,12,13)

> <INCHI_KEY>
VHPXSVXJBWZORQ-UHFFFAOYSA-N

> <FORMULA>
C6H7N5O2

> <MOLECULAR_WEIGHT>
181.1521

> <EXACT_MASS>
181.059974493

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
16.2912202012509

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-7-methyl-6,7,8,9-tetrahydro-3H-purine-6,8-dione

> <ALOGPS_LOGP>
-1.15

> <JCHEM_LOGP>
-1.5916920126666665

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.299485697361225

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.173445997577497

> <JCHEM_PKA_STRONGEST_BASIC>
0.5126020101796166

> <JCHEM_POLAR_SURFACE_AREA>
99.82000000000001

> <JCHEM_REFRACTIVITY>
52.5045

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-7-methyl-3,9-dihydropurine-6,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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      37.036  -7.947   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      31.806 -11.027   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      34.597  -9.186   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      34.597  -6.707   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      31.806  -6.407   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      30.472  -8.717   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      29.138  -6.407   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      33.140  -8.717   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.140  -7.177   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.496  -7.947   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.806  -9.487   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.075 -10.650   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.472  -7.177   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3    8   10   12                                                  
CONECT    4    9   10                                                       
CONECT    5    9   13                                                       
CONECT    6   11   13                                                       
CONECT    7   13                                                            
CONECT    8    3    9   11                                                  
CONECT    9    4    5    8                                                  
CONECT   10    1    3    4                                                  
CONECT   11    2    6    8                                                  
CONECT   12    3                                                            
CONECT   13    5    6    7                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₆H₇N₅O₂

Average Molecular Weight

181.1521

Monoisotopic Molecular Weight

181.059974493

IUPAC Name

2-amino-7-methyl-6,7,8,9-tetrahydro-3H-purine-6,8-dione

Traditional Name

2-amino-7-methyl-3,9-dihydropurine-6,8-dione

CAS Registry Number

1688-85-3

SMILES

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

InChI Identifier

InChI=1S/C6H7N5O2/c1-11-2-3(9-6(11)13)8-5(7)10-4(2)12/h1H3,(H4,7,8,9,10,12,13)

InChI Key

VHPXSVXJBWZORQ-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
Vinylogous amide
Imidazole
Azole
Heteroaromatic compound
Urea
Azacycle
Organic oxide
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:74064 )
2-aminopurines (CHEBI:74064 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006037)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006037)

Source

Endogenous

Endogenous (HMDB: HMDB0006037)

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	3.03 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.6	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.17	ChemAxon
pKa (Strongest Basic)	0.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.5 m³·mol⁻¹	ChemAxon
Polarizability	16.29 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]+	139.522	31661259
DarkChem	[M-H]-	136.648	31661259
DeepCCS	[M+H]+	134.187	30932474
DeepCCS	[M-H]-	131.792	30932474
DeepCCS	[M-2H]-	167.089	30932474
DeepCCS	[M+Na]+	141.544	30932474
AllCCS	[M+H]+	138.7	32859911
AllCCS	[M+H-H2O]+	134.3	32859911
AllCCS	[M+NH4]+	142.7	32859911
AllCCS	[M+Na]+	143.8	32859911
AllCCS	[M-H]-	135.4	32859911
AllCCS	[M+Na-2H]-	135.9	32859911
AllCCS	[M+HCOO]-	136.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxy-7-methylguanine	CN1C(=O)NC2=C1C(=O)N=C(N)N2	2917.7	Standard polar	33892256
8-Hydroxy-7-methylguanine	CN1C(=O)NC2=C1C(=O)N=C(N)N2	2100.9	Standard non polar	33892256
8-Hydroxy-7-methylguanine	CN1C(=O)NC2=C1C(=O)N=C(N)N2	2313.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxy-7-methylguanine,1TMS,isomer #1	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C)[NH]2	2150.3	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,1TMS,isomer #1	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C)[NH]2	2262.0	Standard non polar	33892256
8-Hydroxy-7-methylguanine,1TMS,isomer #1	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C)[NH]2	3415.9	Standard polar	33892256
8-Hydroxy-7-methylguanine,1TMS,isomer #2	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N)[NH]2	2100.8	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,1TMS,isomer #2	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N)[NH]2	2273.2	Standard non polar	33892256
8-Hydroxy-7-methylguanine,1TMS,isomer #2	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N)[NH]2	3291.9	Standard polar	33892256
8-Hydroxy-7-methylguanine,1TMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N)N2[Si](C)(C)C	2091.2	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,1TMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N)N2[Si](C)(C)C	2241.1	Standard non polar	33892256
8-Hydroxy-7-methylguanine,1TMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N)N2[Si](C)(C)C	3328.4	Standard polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C)[NH]2	2045.1	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C)[NH]2	2290.7	Standard non polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C)[NH]2	3080.9	Standard polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #2	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C)N2[Si](C)(C)C	2049.4	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #2	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C)N2[Si](C)(C)C	2285.7	Standard non polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #2	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C)N2[Si](C)(C)C	2995.3	Standard polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]2	2038.3	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]2	2256.0	Standard non polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]2	2967.2	Standard polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #4	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N)N2[Si](C)(C)C	2051.4	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #4	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N)N2[Si](C)(C)C	2284.2	Standard non polar	33892256
8-Hydroxy-7-methylguanine,2TMS,isomer #4	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N)N2[Si](C)(C)C	3074.4	Standard polar	33892256
8-Hydroxy-7-methylguanine,3TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C)N2[Si](C)(C)C	2081.2	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,3TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C)N2[Si](C)(C)C	2307.6	Standard non polar	33892256
8-Hydroxy-7-methylguanine,3TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C)N2[Si](C)(C)C	2735.2	Standard polar	33892256
8-Hydroxy-7-methylguanine,3TMS,isomer #2	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]2	2052.6	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,3TMS,isomer #2	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]2	2257.4	Standard non polar	33892256
8-Hydroxy-7-methylguanine,3TMS,isomer #2	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]2	2603.6	Standard polar	33892256
8-Hydroxy-7-methylguanine,3TMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N2[Si](C)(C)C	2098.6	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,3TMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N2[Si](C)(C)C	2321.1	Standard non polar	33892256
8-Hydroxy-7-methylguanine,3TMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N2[Si](C)(C)C	2605.9	Standard polar	33892256
8-Hydroxy-7-methylguanine,4TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N2[Si](C)(C)C	2195.5	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,4TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N2[Si](C)(C)C	2351.5	Standard non polar	33892256
8-Hydroxy-7-methylguanine,4TMS,isomer #1	CN1C(=O)N([Si](C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N2[Si](C)(C)C	2393.9	Standard polar	33892256
8-Hydroxy-7-methylguanine,1TBDMS,isomer #1	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]2	2351.4	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,1TBDMS,isomer #1	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]2	2445.4	Standard non polar	33892256
8-Hydroxy-7-methylguanine,1TBDMS,isomer #1	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]2	3361.4	Standard polar	33892256
8-Hydroxy-7-methylguanine,1TBDMS,isomer #2	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N)[NH]2	2303.9	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,1TBDMS,isomer #2	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N)[NH]2	2447.8	Standard non polar	33892256
8-Hydroxy-7-methylguanine,1TBDMS,isomer #2	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N)[NH]2	3268.9	Standard polar	33892256
8-Hydroxy-7-methylguanine,1TBDMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N)N2[Si](C)(C)C(C)(C)C	2318.5	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,1TBDMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N)N2[Si](C)(C)C(C)(C)C	2435.1	Standard non polar	33892256
8-Hydroxy-7-methylguanine,1TBDMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N)N2[Si](C)(C)C(C)(C)C	3279.3	Standard polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]2	2417.3	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]2	2660.8	Standard non polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]2	3035.8	Standard polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #2	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2495.3	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #2	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2706.1	Standard non polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #2	CN1C(=O)[NH]C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2964.7	Standard polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]2	2436.8	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]2	2677.1	Standard non polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]2	2943.4	Standard polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #4	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N)N2[Si](C)(C)C(C)(C)C	2467.2	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #4	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N)N2[Si](C)(C)C(C)(C)C	2690.4	Standard non polar	33892256
8-Hydroxy-7-methylguanine,2TBDMS,isomer #4	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N)N2[Si](C)(C)C(C)(C)C	3053.0	Standard polar	33892256
8-Hydroxy-7-methylguanine,3TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2647.9	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,3TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2917.4	Standard non polar	33892256
8-Hydroxy-7-methylguanine,3TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2876.3	Standard polar	33892256
8-Hydroxy-7-methylguanine,3TBDMS,isomer #2	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]2	2579.4	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,3TBDMS,isomer #2	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]2	2893.5	Standard non polar	33892256
8-Hydroxy-7-methylguanine,3TBDMS,isomer #2	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]2	2793.0	Standard polar	33892256
8-Hydroxy-7-methylguanine,3TBDMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2661.5	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,3TBDMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2958.2	Standard non polar	33892256
8-Hydroxy-7-methylguanine,3TBDMS,isomer #3	CN1C(=O)[NH]C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2788.1	Standard polar	33892256
8-Hydroxy-7-methylguanine,4TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2851.7	Semi standard non polar	33892256
8-Hydroxy-7-methylguanine,4TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	3153.8	Standard non polar	33892256
8-Hydroxy-7-methylguanine,4TBDMS,isomer #1	CN1C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C	2765.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-7-methylguanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-0900000000-4e0a1211082933a52189	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-7-methylguanine 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 - 8-Hydroxy-7-methylguanine 10V, Positive-QTOF	splash10-001i-0900000000-7c1b5b61581c8650b910	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-7-methylguanine 20V, Positive-QTOF	splash10-001i-0900000000-15a7e1a0805e52238283	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-7-methylguanine 40V, Positive-QTOF	splash10-00rb-7900000000-b9f171dba84ae611184a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-7-methylguanine 10V, Negative-QTOF	splash10-001i-0900000000-ca5228f6b8181c8393ab	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-7-methylguanine 20V, Negative-QTOF	splash10-001r-1900000000-8ad42ac014332bbefdc5	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-7-methylguanine 40V, Negative-QTOF	splash10-0007-9200000000-a717cec7a8c28103e4aa	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-7-methylguanine 10V, Negative-QTOF	splash10-001i-0900000000-90d288c41daa0d7f9fe7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-7-methylguanine 20V, Negative-QTOF	splash10-001i-0900000000-27306b4f0abc07f63593	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-7-methylguanine 40V, Negative-QTOF	splash10-0006-9200000000-0f5e5385863ab5177669	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-7-methylguanine 10V, Positive-QTOF	splash10-001i-0900000000-e9758175f80068d624c4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-7-methylguanine 20V, Positive-QTOF	splash10-001i-0900000000-0b6d69fb729f5067e205	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-7-methylguanine 40V, Positive-QTOF	splash10-000l-5900000000-32125fca442ba581cefa	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.6 (0.4-0.72) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	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

FDB023813

KNApSAcK ID

Not Available

Chemspider ID

272336

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

308075

PDB ID

Not Available

ChEBI ID

74064

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)

Not Available

General References

Niwa T, Takeda N, Yoshizumi H: RNA metabolism in uremic patients: accumulation of modified ribonucleosides in uremic serum. Technical note. Kidney Int. 1998 Jun;53(6):1801-6. [PubMed:9607216 ]
Choi JY, Guengerich FP: Adduct size limits efficient and error-free bypass across bulky N2-guanine DNA lesions by human DNA polymerase eta. J Mol Biol. 2005 Sep 9;352(1):72-90. [PubMed:16061253 ]
Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [PubMed:3506820 ]
Kanduc D, Sapia G: Origin of 1,7-dimethylguanosine in tRNA chemical and enzymatic methylation. Boll Soc Ital Biol Sper. 1982 Oct 15;58(19):1221-5. [PubMed:7159514 ]
Litwack MD, Weissmann B: Source of urinary 8-hydroxy-7-methylguanine in man. Biochemistry. 1966 Sep;5(9):3007-12. [PubMed:5961889 ]
Choi JY, Guengerich FP: Kinetic evidence for inefficient and error-prone bypass across bulky N2-guanine DNA adducts by human DNA polymerase iota. J Biol Chem. 2006 May 5;281(18):12315-24. Epub 2006 Mar 8. [PubMed:16527824 ]
Porcelli B, Pagani R, Lorenzini L, De Martino A, Catinella S, Traldi P: Different mass spectrometric approaches in the identification of endogenous methylated purine bases in urine extracts. Rapid Commun Mass Spectrom. 1994 Jun;8(6):443-50. [PubMed:8043914 ]
Sander G, Topp H, Heller-Schoch G, Wieland J, Schoch G: Ribonucleic acid turnover in man:RNA catabolites in urine as measure for the metabolism of each of the three major species of RNA. Clin Sci (Lond). 1986 Oct;71(4):367-74. [PubMed:2428556 ]

Showing metabocard for 8-Hydroxy-7-methylguanine (HMDB0006037)

MOL for HMDB0006037 (8-Hydroxy-7-methylguanine)

3D MOL for HMDB0006037 (8-Hydroxy-7-methylguanine)

3D SDF for HMDB0006037 (8-Hydroxy-7-methylguanine)

3D-SDF for HMDB0006037 (8-Hydroxy-7-methylguanine)

PDB for HMDB0006037 (8-Hydroxy-7-methylguanine)

3D PDB for HMDB0006037 (8-Hydroxy-7-methylguanine)

SMILES for HMDB0006037 (8-Hydroxy-7-methylguanine)

INCHI for HMDB0006037 (8-Hydroxy-7-methylguanine)

Structure for HMDB0006037 (8-Hydroxy-7-methylguanine)

3D Structure for HMDB0006037 (8-Hydroxy-7-methylguanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra