NP-MRD: Showing NP-Card for 1-Methyladenosine (NP0000685)

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Record Information

Version

1.0

Created at

2006-08-02 10:18:02 UTC

Updated at

2021-06-29 00:47:44 UTC

NP-MRD ID

NP0000685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-Methyladenosine

Description

1-Methyladenosine, also known as M1A, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Precise m6A mapping by m6A-CLIP/IP (briefly m6A-CLIP) revealed that a majority of m6A locates in the last exon of mRNAs in multiple tissues/cultured cells of mouse and human, and the m6A enrichment around stop codons is a coincidence that many stop codons locate round the start of last exons where m6A is truly enriched. The methylation of adenosine is directed by a large m6A methyltransferase complex containing METTL3 as the SAM-binding sub-unit. Insulin-like growth factor-2 mRNA-binding proteins 1, 2, and 3 (IGF2BP1-3) are reported as a novel class of m6A readers.

Structure

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

HMDB0003331
     RDKit          3D
1-Methyladenosine
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.5707    0.0455    0.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1020    0.0168    0.2748 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3485    0.4348    1.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933    0.4113    1.2376 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703   -0.0260    0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1102   -0.4682   -0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -0.8509   -1.9282 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -0.6403   -1.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0909   -0.1489   -0.1854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0482    0.1881    0.6448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8340   -0.9041    0.8939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449   -0.5908    0.7120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7387   -1.5658   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0837   -1.2918   -0.5249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2774    0.8290    0.2963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8417    1.5552    1.3222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8743    1.2326   -0.0389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5288    2.4806    0.4283 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850   -0.4202   -0.8253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1863   -0.8214   -1.8208 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9078    0.4821    1.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9004    0.6508   -0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9092   -0.9850    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    0.7842    2.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759   -0.8625   -1.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198    0.6045    1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6939   -0.7999    1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6735   -2.5807    0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1686   -1.6090   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6535   -2.0816   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174    0.8808   -0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544    2.5165    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7270    1.1180   -1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8808    3.2260   -0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -0.8094   -1.7788 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  2  3
 19  2  1  0
  9  5  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  8 25  1  0
 10 26  1  1
 12 27  1  1
 13 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  6
 16 32  1  0
 17 33  1  6
 18 34  1  0
 20 35  1  0
M  END


  Mrv1652305261923512D          

 20 22  0  0  1  0            999 V2000
   24.7667  -11.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9165  -14.5245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9196  -12.7296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9811  -13.6237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9989  -16.1526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2085  -15.0762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7135  -17.3901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7135  -14.9151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2085  -16.4041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2136  -12.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2844  -16.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4649  -14.2920    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.4672  -12.9571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.2499  -14.0384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.2514  -13.2134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.7135  -16.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4279  -15.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4279  -16.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9989  -15.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6900  -15.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
 14  2  1  1  0  0  0
 15  3  1  1  0  0  0
  4 12  1  0  0  0  0
  4 13  1  0  0  0  0
  5 11  1  0  0  0  0
  5 16  1  0  0  0  0
  5 19  1  0  0  0  0
 12  6  1  6  0  0  0
  6 17  1  0  0  0  0
  6 20  1  0  0  0  0
  7 16  2  0  0  0  0
  8 17  1  0  0  0  0
  8 19  2  0  0  0  0
  9 18  1  0  0  0  0
  9 20  2  0  0  0  0
 13 10  1  6  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 16 18  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=N

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N5O4/c1-15-3-14-10-6(9(15)12)13-4-16(10)11-8(19)7(18)5(2-17)20-11/h3-5,7-8,11-12,17-19H,2H2,1H3/t5-,7-,8-,11-/m1/s1

> <INCHI_KEY>
GFYLSDSUCHVORB-IOSLPCCCSA-N

> <FORMULA>
C11H15N5O4

> <MOLECULAR_WEIGHT>
281.2679

> <EXACT_MASS>
281.112403993

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.563246143793226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-imino-1-methyl-6,9-dihydro-1H-purin-9-yl)oxolane-3,4-diol

> <ALOGPS_LOGP>
-1.83

> <JCHEM_LOGP>
-2.0928004579999993

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.891226123045147

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.454003933524138

> <JCHEM_PKA_STRONGEST_BASIC>
2.9779712827203126

> <JCHEM_POLAR_SURFACE_AREA>
127.19

> <JCHEM_REFRACTIVITY>
79.0985

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyladenosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003331
     RDKit          3D
1-Methyladenosine
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.5707    0.0455    0.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1020    0.0168    0.2748 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3485    0.4348    1.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933    0.4113    1.2376 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703   -0.0260    0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1102   -0.4682   -0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -0.8509   -1.9282 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -0.6403   -1.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0909   -0.1489   -0.1854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0482    0.1881    0.6448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8340   -0.9041    0.8939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449   -0.5908    0.7120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7387   -1.5658   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0837   -1.2918   -0.5249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2774    0.8290    0.2963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8417    1.5552    1.3222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8743    1.2326   -0.0389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5288    2.4806    0.4283 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850   -0.4202   -0.8253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1863   -0.8214   -1.8208 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9078    0.4821    1.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9004    0.6508   -0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9092   -0.9850    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    0.7842    2.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759   -0.8625   -1.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198    0.6045    1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6939   -0.7999    1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6735   -2.5807    0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1686   -1.6090   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6535   -2.0816   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174    0.8808   -0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544    2.5165    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7270    1.1180   -1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8808    3.2260   -0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -0.8094   -1.7788 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  2  3
 19  2  1  0
  9  5  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  8 25  1  0
 10 26  1  1
 12 27  1  1
 13 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  6
 16 32  1  0
 17 33  1  6
 18 34  1  0
 20 35  1  0
M  END

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  O   UNK     0      46.231 -21.578   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      48.377 -27.112   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      48.383 -23.762   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      44.765 -25.431   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      41.065 -30.152   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      45.189 -28.142   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      42.399 -32.462   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      42.399 -27.842   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      45.189 -30.621   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      45.199 -22.721   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      39.731 -30.922   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      45.668 -26.678   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      45.672 -24.187   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      47.133 -26.205   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.136 -24.665   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.399 -30.922   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      43.732 -28.612   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      43.732 -30.152   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.065 -28.612   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      46.088 -29.382   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   12   13                                                       
CONECT    5   11   16   19                                                  
CONECT    6   12   17   20                                                  
CONECT    7   16                                                            
CONECT    8   17   19                                                       
CONECT    9   18   20                                                       
CONECT   10    1   13                                                       
CONECT   11    5                                                            
CONECT   12    4    6   14                                                  
CONECT   13    4   10   15                                                  
CONECT   14    2   12   15                                                  
CONECT   15    3   13   14                                                  
CONECT   16    5    7   18                                                  
CONECT   17    6    8   18                                                  
CONECT   18    9   16   17                                                  
CONECT   19    5    8                                                       
CONECT   20    6    9                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0003331
HETATM    1  C1  UNL     1       5.571   0.045   0.363  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.102   0.017   0.275  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.348   0.435   1.312  1.00  0.00           C  
HETATM    4  N2  UNL     1       1.993   0.411   1.238  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.370  -0.026   0.136  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.110  -0.468  -0.961  1.00  0.00           C  
HETATM    7  N3  UNL     1       1.255  -0.851  -1.928  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.020  -0.640  -1.415  1.00  0.00           C  
HETATM    9  N4  UNL     1       0.091  -0.149  -0.185  1.00  0.00           N  
HETATM   10  C6  UNL     1      -1.048   0.188   0.645  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.834  -0.904   0.894  1.00  0.00           O  
HETATM   12  C7  UNL     1      -3.145  -0.591   0.712  1.00  0.00           C  
HETATM   13  C8  UNL     1      -3.739  -1.566  -0.299  1.00  0.00           C  
HETATM   14  O2  UNL     1      -5.084  -1.292  -0.525  1.00  0.00           O  
HETATM   15  C9  UNL     1      -3.277   0.829   0.296  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.842   1.555   1.322  1.00  0.00           O  
HETATM   17  C10 UNL     1      -1.874   1.233  -0.039  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.529   2.481   0.428  1.00  0.00           O  
HETATM   19  C11 UNL     1       3.485  -0.420  -0.825  1.00  0.00           C  
HETATM   20  N5  UNL     1       4.186  -0.821  -1.821  1.00  0.00           N  
HETATM   21  H1  UNL     1       5.908   0.482   1.300  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.900   0.651  -0.532  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.909  -0.985   0.207  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.875   0.784   2.192  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.876  -0.863  -1.982  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.720   0.605   1.619  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.694  -0.800   1.676  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.673  -2.581   0.189  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.169  -1.609  -1.231  1.00  0.00           H  
HETATM   30  H10 UNL     1      -5.654  -2.082  -0.405  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.917   0.881  -0.610  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.654   2.516   1.285  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.727   1.118  -1.134  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.881   3.226  -0.103  1.00  0.00           H  
HETATM   35  H15 UNL     1       5.212  -0.809  -1.779  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   19
CONECT    3    4    4   24
CONECT    4    5
CONECT    5    6    6    9
CONECT    6    7   19
CONECT    7    8    8
CONECT    8    9   25
CONECT    9   10
CONECT   10   11   17   26
CONECT   11   12
CONECT   12   13   15   27
CONECT   13   14   28   29
CONECT   14   30
CONECT   15   16   17   31
CONECT   16   32
CONECT   17   18   33
CONECT   18   34
CONECT   19   20   20
CONECT   20   35
END

HMDB0003331
     RDKit          3D
1-Methyladenosine
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.5707    0.0455    0.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1020    0.0168    0.2748 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3485    0.4348    1.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933    0.4113    1.2376 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703   -0.0260    0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1102   -0.4682   -0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -0.8509   -1.9282 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -0.6403   -1.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0909   -0.1489   -0.1854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0482    0.1881    0.6448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8340   -0.9041    0.8939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449   -0.5908    0.7120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7387   -1.5658   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0837   -1.2918   -0.5249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2774    0.8290    0.2963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8417    1.5552    1.3222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8743    1.2326   -0.0389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5288    2.4806    0.4283 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850   -0.4202   -0.8253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1863   -0.8214   -1.8208 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9078    0.4821    1.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9004    0.6508   -0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9092   -0.9850    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    0.7842    2.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759   -0.8625   -1.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198    0.6045    1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6939   -0.7999    1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6735   -2.5807    0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1686   -1.6090   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6535   -2.0816   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174    0.8808   -0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544    2.5165    1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7270    1.1180   -1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8808    3.2260   -0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2125   -0.8094   -1.7788 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  6 19  1  0
 19 20  2  3
 19  2  1  0
  9  5  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  8 25  1  0
 10 26  1  1
 12 27  1  1
 13 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  6
 16 32  1  0
 17 33  1  6
 18 34  1  0
 20 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
m1a	ChEBI
N1-Methyladenosine	HMDB
N(1)-Methyladenosine	HMDB

Chemical Formula

C₁₁H₁₅N₅O₄

Average Mass

281.2679 Da

Monoisotopic Mass

281.11240 Da

IUPAC Name

(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-imino-1-methyl-6,9-dihydro-1H-purin-9-yl)oxolane-3,4-diol

Traditional Name

1-methyladenosine

CAS Registry Number

15763-06-1

SMILES

CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=N

InChI Identifier

InChI=1S/C11H15N5O4/c1-15-3-14-10-6(9(15)12)13-4-16(10)11-8(19)7(18)5(2-17)20-11/h3-5,7-8,11-12,17-19H,2H2,1H3/t5-,7-,8-,11-/m1/s1

InChI Key

GFYLSDSUCHVORB-IOSLPCCCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Daphnia pulex	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
Imidazopyrimidine
Purine
Monosaccharide
N-substituted imidazole
Imidolactam
Pyrimidine
Heteroaromatic compound
Azole
Imidazole
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Primary alcohol
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyladenosine (CHEBI:16020 )

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
Water Solubility	7.33 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	2.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	127.19 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.1 m³·mol⁻¹	ChemAxon
Polarizability	27.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003331

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

N6-Methyladenosine

METLIN ID

6888

PubChem Compound

27476

PDB ID

Not Available

ChEBI ID

16020

Good Scents ID

Not Available

References

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Lee SH, Jung BH, Kim SY, Chung BC: A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7. [PubMed:15116424 ]
Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed:9129323 ]
Uziel M, Smith LH, Taylor SA: Modified nucleosides in urine: selective removal and analysis. Clin Chem. 1976 Sep;22(9):1451-5. [PubMed:954194 ]
Reynaud C, Bruno C, Boullanger P, Grange J, Barbesti S, Niveleau A: Monitoring of urinary excretion of modified nucleosides in cancer patients using a set of six monoclonal antibodies. Cancer Lett. 1992 Jan 31;61(3):255-62. [PubMed:1739950 ]
Zheng YF, Yang J, Zhao XJ, Feng B, Kong HW, Chen YJ, Lv S, Zheng MH, Xu GW: Urinary nucleosides as biological markers for patients with colorectal cancer. World J Gastroenterol. 2005 Jul 7;11(25):3871-6. [PubMed:15991285 ]
Takahashi R, Shiono T, Tamai M, Itoh K, Mizugaki M: [Expression of modified nucleoside, 1-methyladenosine in intraocular tumors and the retinas]. Nippon Ganka Gakkai Zasshi. 1993 Jan;97(1):43-9. [PubMed:8434538 ]

Showing NP-Card for 1-Methyladenosine (NP0000685)

MOL for NP0000685 (1-Methyladenosine)

3D MOL for NP0000685 (1-Methyladenosine)

3D SDF for NP0000685 (1-Methyladenosine)

3D-SDF for NP0000685 (1-Methyladenosine)

PDB for NP0000685 (1-Methyladenosine)

3D PDB for NP0000685 (1-Methyladenosine)

SMILES for NP0000685 (1-Methyladenosine)

INCHI for NP0000685 (1-Methyladenosine)

Structure for NP0000685 (1-Methyladenosine)

3D Structure for NP0000685 (1-Methyladenosine)