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Showing NP-Card for 3-Methyladenine (NP0000353)

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Record Information
Version1.0
Created at2009-01-29 12:14:58 UTC
Updated at2021-06-30 02:06:18 UTC
NP-MRD IDNP0000353
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methyladenine
Description3-Methyladenine, also known as 3-ma nucleobase, 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. 3-Methyladenine exists in all living species, ranging from bacteria to humans. 3-Methyladenine has been detected, but not quantified, in several different foods, such as soft-necked garlics, chinese bayberries, burbots, amaranths, and tea. This could make 3-methyladenine a potential biomarker for the consumption of these foods. 3-Methyladenine is one of the purines damaged by alkylation and oxidation which can be recognized and excised by the human 3-methyladenine DNA glycosylase (AAG) (EC: EC3.2.2.21).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000353 (3-Methyladenine)


  Mrv1652305261923572D          

 11 12  0  0  0  0            999 V2000
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
  7 11  1  0  0  0  0
M  END
Download

3D MOL for NP0000353 (3-Methyladenine)

HMDB0011600
     RDKit          3D
3-Methyladenine
 18 19  0  0  0  0  0  0  0  0999 V2000
    2.6294   -0.3436    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -0.4720    0.0759 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -1.6856   -0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218   -1.7996   -0.1966 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465   -0.7618   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588   -0.8655   -0.3434 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9915    0.5016   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4686    1.7589   -0.0207 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886    2.6521    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6677    1.9656    0.1955 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4691    0.6635    0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8973   -0.2545    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354   -1.2616   -0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    0.5538   -0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427   -2.5793   -0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4848   -1.7218   -0.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5325   -0.0876   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6402    3.7374    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  2  1  0
 11  7  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  6 16  1  0
  6 17  1  0
  9 18  1  0
M  END
Download

3D SDF for NP0000353 (3-Methyladenine)


  Mrv1652305261923572D          

 11 12  0  0  0  0            999 V2000
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
  7 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000353

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC(N)=C2N=CN=C12

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

> <INCHI_KEY>
FSASIHFSFGAIJM-UHFFFAOYSA-N

> <FORMULA>
C6H7N5

> <MOLECULAR_WEIGHT>
149.1533

> <EXACT_MASS>
149.070145249

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.47668525793151

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methyl-3H-purin-6-amine

> <ALOGPS_LOGP>
-1.14

> <JCHEM_LOGP>
-0.3073366643333334

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.30023185725119

> <JCHEM_PKA_STRONGEST_BASIC>
3.0308081279002455

> <JCHEM_POLAR_SURFACE_AREA>
69.62

> <JCHEM_REFRACTIVITY>
41.495999999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methyladenine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000353 (3-Methyladenine)

HMDB0011600
     RDKit          3D
3-Methyladenine
 18 19  0  0  0  0  0  0  0  0999 V2000
    2.6294   -0.3436    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -0.4720    0.0759 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -1.6856   -0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218   -1.7996   -0.1966 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465   -0.7618   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588   -0.8655   -0.3434 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9915    0.5016   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4686    1.7589   -0.0207 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886    2.6521    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6677    1.9656    0.1955 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4691    0.6635    0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8973   -0.2545    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354   -1.2616   -0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    0.5538   -0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427   -2.5793   -0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4848   -1.7218   -0.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5325   -0.0876   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6402    3.7374    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  2  1  0
 11  7  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  6 16  1  0
  6 17  1  0
  9 18  1  0
M  END
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PDB for NP0000353 (3-Methyladenine)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.121  -2.310   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for NP0000353 (3-Methyladenine)

COMPND    HMDB0011600
HETATM    1  C1  UNL     1       2.629  -0.344   0.221  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.189  -0.472   0.076  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.619  -1.686  -0.062  1.00  0.00           C  
HETATM    4  N2  UNL     1      -0.722  -1.800  -0.197  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.547  -0.762  -0.203  1.00  0.00           C  
HETATM    6  N3  UNL     1      -2.959  -0.865  -0.343  1.00  0.00           N  
HETATM    7  C4  UNL     1      -0.992   0.502  -0.063  1.00  0.00           C  
HETATM    8  N4  UNL     1      -1.469   1.759  -0.021  1.00  0.00           N  
HETATM    9  C5  UNL     1      -0.489   2.652   0.134  1.00  0.00           C  
HETATM   10  N5  UNL     1       0.668   1.966   0.196  1.00  0.00           N  
HETATM   11  C6  UNL     1       0.469   0.664   0.087  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.897  -0.255   1.298  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.135  -1.262  -0.148  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.984   0.554  -0.307  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.243  -2.579  -0.065  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.485  -1.722  -0.060  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.533  -0.088  -0.738  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.640   3.737   0.195  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   11
CONECT    3    4    4   15
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   16   17
CONECT    7    8   11
CONECT    8    9    9
CONECT    9   10   18
CONECT   10   11   11
END
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SMILES for NP0000353 (3-Methyladenine)

CN1C=NC(N)=C2N=CN=C12
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INCHI for NP0000353 (3-Methyladenine)

InChI=1S/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3
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View in JSmol
Synonyms
ValueSource
3-Methyl-3H-adenineChEBI
3-METHYL-3H-purin-6-ylamineChEBI
6-Amino-3-methylpurineChEBI
3-Methyl-3H-purin-6-amineHMDB
3-Methyl-3H-purin-6-amine (acd/name 4.0)HMDB
3-Methyl-3H-purin-6-ylamine (acd/name 4.0)HMDB
3-Methyl-adenineHMDB
3-MA nucleobaseHMDB
N(3)-MethyladenineHMDB
Chemical FormulaC6H7N5
Average Mass149.1533 Da
Monoisotopic Mass149.07015 Da
IUPAC Name3-methyl-3H-purin-6-amine
Traditional Name3-methyladenine
CAS Registry Number5142-23-4
SMILES
CN1C=NC(N)=C2N=CN=C12
InChI Identifier
InChI=1S/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3
InChI KeyFSASIHFSFGAIJM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.81 g/LALOGPS
logP-1.1ALOGPS
logP-0.31ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)17.3ChemAxon
pKa (Strongest Basic)3.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.5 m³·mol⁻¹ChemAxon
Polarizability14.48 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011600
DrugBank IDDB04104
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028311
KNApSAcK IDNot Available
Chemspider ID1610
KEGG Compound IDC00913
BioCyc ID3-Methyl-Adenines
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1673
PDB IDADK
ChEBI ID38635
Good Scents IDNot Available
References
General References
  1. Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
  2. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
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  4. Huang YT, Cheng CC, Lin TC, Chiu TH, Lai PC: Therapeutic potential of sepantronium bromide YM155 in gemcitabine-resistant human urothelial carcinoma cells. Oncol Rep. 2014 Feb;31(2):771-80. doi: 10.3892/or.2013.2882. Epub 2013 Nov 28. [PubMed:24297644 ]
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