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Showing NP-Card for 6-Methyladenine (NP0001467)

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Record Information
Version1.0
Created at2006-05-22 14:17:36 UTC
Updated at2021-06-29 00:47:22 UTC
NP-MRD IDNP0001467
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-Methyladenine
Description6-Methyladenine is a methylated adenine residue. The formation of internal 6-methyladenine (m6A) residues in eucaryotic messenger RNA (mRNA) is a postsynthetic modification in which S-adenosyl-L-methionine (SAM) serves as the methyl donor. 6-Methyladenine residues have also been localized to heterogeneous nuclear RNA (HnRNA), and for the most part these residues are conserved during mRNA processing. Although the biological significance of internal adenine methylation in eucaryotic mRNA remains unclear, a great deal of research has indicated that this modification may be required for mRNA transport to the cytoplasm, the selection of splice sites or other RNA processing reactions. The presence of m6A residues increases the in vitro translation efficiency of dihydrofolate reductase; an inhibition of m6A residues in dihydrofolate reductase transcripts significantly alters their rate of translation. M6A is found in many human fluids: Oviductal fluid, blood plasma and urine (PMID: 1551452 , 8925412 , 10481270 , 16083005 , 16684535 , 3506820 , 3728186 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001467 (6-Methyladenine)


  Mrv1652305271900012D          

 11 12  0  0  0  0            999 V2000
   18.3659   -4.7812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8708   -3.7949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3659   -6.1089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1562   -5.0326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8708   -6.2701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5853   -5.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8708   -4.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5853   -5.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8475   -5.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1562   -5.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1562   -3.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  2  7  1  0  0  0  0
  2 11  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  2  0  0  0  0
  4  7  2  0  0  0  0
  4 10  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
Download

3D MOL for NP0001467 (6-Methyladenine)

HMDB0002099
     RDKit          3D
6-Methyladenine
 18 19  0  0  0  0  0  0  0  0999 V2000
    2.8474   -0.4126    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373   -0.7473    0.2023 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4497    0.2431    0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7058    1.5562    0.0925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2463    2.4913   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5199    2.0862   -0.2212 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8815    0.7907   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0366    0.1193   -0.4278 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7901   -1.1963   -0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -1.3503   -0.2031 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607   -0.1386   -0.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4740   -0.7740   -0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9071    0.6916    0.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -0.8886    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1657   -1.7543    0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0184    3.5519   -0.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895   -2.0319   -0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170   -2.2366   -0.1233 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  3  1  0
 11  7  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  5 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

3D SDF for NP0001467 (6-Methyladenine)


  Mrv1652305271900012D          

 11 12  0  0  0  0            999 V2000
   18.3659   -4.7812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8708   -3.7949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3659   -6.1089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1562   -5.0326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8708   -6.2701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5853   -5.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8708   -4.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5853   -5.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8475   -5.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1562   -5.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1562   -3.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  2  7  1  0  0  0  0
  2 11  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  2  0  0  0  0
  4  7  2  0  0  0  0
  4 10  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001467

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC1=NC=NC2=C1NC=N2

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

> <INCHI_KEY>
CKOMXBHMKXXTNW-UHFFFAOYSA-N

> <FORMULA>
C6H7N5

> <MOLECULAR_WEIGHT>
149.1533

> <EXACT_MASS>
149.070145249

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.431311219735017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-methyl-7H-purin-6-amine

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
-0.2717661493333333

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.239390777889598

> <JCHEM_PKA_STRONGEST_BASIC>
3.494896428364796

> <JCHEM_POLAR_SURFACE_AREA>
66.49000000000001

> <JCHEM_REFRACTIVITY>
43.7129

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(methylamino)purine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001467 (6-Methyladenine)

HMDB0002099
     RDKit          3D
6-Methyladenine
 18 19  0  0  0  0  0  0  0  0999 V2000
    2.8474   -0.4126    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373   -0.7473    0.2023 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4497    0.2431    0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7058    1.5562    0.0925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2463    2.4913   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5199    2.0862   -0.2212 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8815    0.7907   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0366    0.1193   -0.4278 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7901   -1.1963   -0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -1.3503   -0.2031 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607   -0.1386   -0.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4740   -0.7740   -0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9071    0.6916    0.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -0.8886    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1657   -1.7543    0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0184    3.5519   -0.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895   -2.0319   -0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170   -2.2366   -0.1233 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  3  1  0
 11  7  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  5 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

PDB for NP0001467 (6-Methyladenine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0      34.283  -8.925   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0      31.492  -7.084   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      34.283 -11.403   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      30.158  -9.394   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      31.492 -11.704   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      32.826  -9.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.492  -8.624   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.826 -10.934   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.182 -10.164   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.158 -10.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.158  -6.314   0.000  0.00  0.00           C+0
CONECT    1    6    9                                                       
CONECT    2    7   11                                                       
CONECT    3    8    9                                                       
CONECT    4    7   10                                                       
CONECT    5    8   10                                                       
CONECT    6    1    7    8                                                  
CONECT    7    2    4    6                                                  
CONECT    8    3    5    6                                                  
CONECT    9    1    3                                                       
CONECT   10    4    5                                                       
CONECT   11    2                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for NP0001467 (6-Methyladenine)

COMPND    HMDB0002099
HETATM    1  C1  UNL     1       2.847  -0.413   0.399  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.437  -0.747   0.202  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.450   0.243   0.061  1.00  0.00           C  
HETATM    4  N2  UNL     1       0.706   1.556   0.093  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.246   2.491  -0.044  1.00  0.00           C  
HETATM    6  N3  UNL     1      -1.520   2.086  -0.221  1.00  0.00           N  
HETATM    7  C4  UNL     1      -1.881   0.791  -0.268  1.00  0.00           C  
HETATM    8  N4  UNL     1      -3.037   0.119  -0.428  1.00  0.00           N  
HETATM    9  C5  UNL     1      -2.790  -1.196  -0.389  1.00  0.00           C  
HETATM   10  N5  UNL     1      -1.467  -1.350  -0.203  1.00  0.00           N  
HETATM   11  C6  UNL     1      -0.861  -0.139  -0.122  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.474  -0.774  -0.447  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.907   0.692   0.470  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.203  -0.889   1.348  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.166  -1.754   0.167  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.018   3.552  -0.010  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.489  -2.032  -0.485  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.917  -2.237  -0.123  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15
CONECT    3    4    4   11
CONECT    4    5
CONECT    5    6    6   16
CONECT    6    7
CONECT    7    8   11   11
CONECT    8    9    9
CONECT    9   10   17
CONECT   10   11   18
END
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SMILES for NP0001467 (6-Methyladenine)

CNC1=NC=NC2=C1NC=N2
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INCHI for NP0001467 (6-Methyladenine)

InChI=1S/C6H7N5/c1-7-5-4-6(10-2-8-4)11-3-9-5/h2-3H,1H3,(H2,7,8,9,10,11)
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View in JSmol
Synonyms
ValueSource
6-MAPChEBI
6-MethylaminopurineChEBI
N6-MethyladenineChEBI
N6-MonomethyladenineChEBI
(N-6)-MethyladenineHMDB
6-(Methylamino)purineHMDB
6-MonomethylaminopurineHMDB
Methyl(purin-6-yl)amineHMDB
N-6-MethyladenineHMDB
N-Methyl-9H-purin-6-amineHMDB
N-Methyl-adenineHMDB
N-Methyl-N-(9H-purin-6-yl)amineHMDB
N-MethyladenineHMDB
N(6)-MethyladenineHMDB
6-MethyladenineChEBI
Chemical FormulaC6H7N5
Average Mass149.1533 Da
Monoisotopic Mass149.07015 Da
IUPAC NameN-methyl-7H-purin-6-amine
Traditional Name6-(methylamino)purine
CAS Registry Number443-72-1
SMILES
CNC1=NC=NC2=C1NC=N2
InChI Identifier
InChI=1S/C6H7N5/c1-7-5-4-6(10-2-8-4)11-3-9-5/h2-3H,1H3,(H2,7,8,9,10,11)
InChI KeyCKOMXBHMKXXTNW-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
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-alkylaminopurines. 6-Alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. 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-alkylaminopurines
Alternative Parents
Substituents
  • 6-alkylaminopurine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen 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 Solubility1.18 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.94 g/LALOGPS
logP0.19ALOGPS
logP-0.27ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)10.24ChemAxon
pKa (Strongest Basic)3.49ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.49 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.71 m³·mol⁻¹ChemAxon
Polarizability14.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002099
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022845
KNApSAcK IDNot Available
Chemspider ID61270
KEGG Compound IDC08434
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound67955
PDB IDNot Available
ChEBI ID28871
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. Tuck MT: The formation of internal 6-methyladenine residues in eucaryotic messenger RNA. Int J Biochem. 1992 Mar;24(3):379-86. [PubMed:1551452 ]
  3. Heilman KL, Leach RA, Tuck MT: Internal 6-methyladenine residues increase the in vitro translation efficiency of dihydrofolate reductase messenger RNA. Int J Biochem Cell Biol. 1996 Jul;28(7):823-9. [PubMed:8925412 ]
  4. Tuck MT, Wiehl PE, Pan T: Inhibition of 6-methyladenine formation decreases the translation efficiency of dihydrofolate reductase transcripts. Int J Biochem Cell Biol. 1999 Aug;31(8):837-51. [PubMed:10481270 ]
  5. Baniushin BF: [Methylation of adenine residues in DNA of eukaryotes]. Mol Biol (Mosk). 2005 Jul-Aug;39(4):557-66. [PubMed:16083005 ]
  6. Ratel D, Ravanat JL, Charles MP, Platet N, Breuillaud L, Lunardi J, Berger F, Wion D: Undetectable levels of N6-methyl adenine in mouse DNA: Cloning and analysis of PRED28, a gene coding for a putative mammalian DNA adenine methyltransferase. FEBS Lett. 2006 May 29;580(13):3179-84. Epub 2006 May 3. [PubMed:16684535 ]
  7. Morris GS, Simmonds HA: A single system for the evaluation of purine and pyrimidine nucleosides and bases together with their analogues in biological fluids. Adv Exp Med Biol. 1986;195 Pt A:593-9. [PubMed:3728186 ]