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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-02 10:18:02 UTC

Update Date

2021-09-14 14:57:19 UTC

HMDB ID

HMDB0003331

Secondary Accession Numbers

HMDB03331

Metabolite 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>
HMDB0003331

> <DATABASE_NAME>
hmdb

> <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 View NMR Assignments View Stereo Labels

Synonyms

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

Chemical Formula

C₁₁H₁₅N₅O₄

Average Molecular Weight

281.2679

Monoisotopic Molecular Weight

281.112403993

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

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 )

Ontology

Physiological effect

Health effect

Renal system and urinary system

Renal disorder

Kidney disease (HMDB: HMDB0003331)

Cancer

Uremia (HMDB: HMDB0003331)

Digestive system disorder

Gastrointestinal disorder

Stomach cancer (HMDB: HMDB0003331)

Hepatobiliary disorder

Hepatocellular carcinoma (HMDB: HMDB0003331)

Disposition

Biological location

Biofluid or Excreta

Blood (HMDB: HMDB0003331)
Urine (HMDB: HMDB0003331)

Organ

Prostate (HMDB: HMDB0003331)
Placenta (HMDB: HMDB0003331)

Excreta

Biofluid or Excreta

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7482520)

Cellular substructure

Cytoplasm (HMDB: HMDB0003331)

Source

Endogenous

Endogenous (HMDB: HMDB0003331)

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	159.213	30932474
[M+H]+	MetCCS_train_pos	164.21	30932474
[M-H]-	Not Available	162.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002083

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	163.971	31661259
DarkChem	[M-H]-	159.826	31661259
DeepCCS	[M+H]+	160.623	30932474
DeepCCS	[M-H]-	158.265	30932474
DeepCCS	[M-2H]-	192.408	30932474
DeepCCS	[M+Na]+	167.492	30932474
AllCCS	[M+H]+	163.8	32859911
AllCCS	[M+H-H2O]+	160.5	32859911
AllCCS	[M+NH4]+	167.0	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	164.4	32859911
AllCCS	[M+Na-2H]-	164.1	32859911
AllCCS	[M+HCOO]-	163.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Methyladenosine	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=N	3536.0	Standard polar	33892256
1-Methyladenosine	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=N	2650.2	Standard non polar	33892256
1-Methyladenosine	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=N	2804.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Methyladenosine,1TMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O)C1=N	2681.9	Semi standard non polar	33892256
1-Methyladenosine,1TMS,isomer #2	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O)C1=N	2701.2	Semi standard non polar	33892256
1-Methyladenosine,1TMS,isomer #3	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C)C1=N	2688.4	Semi standard non polar	33892256
1-Methyladenosine,1TMS,isomer #4	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=N[Si](C)(C)C	2647.8	Semi standard non polar	33892256
1-Methyladenosine,2TMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C1=N	2646.5	Semi standard non polar	33892256
1-Methyladenosine,2TMS,isomer #2	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C1=N	2631.9	Semi standard non polar	33892256
1-Methyladenosine,2TMS,isomer #3	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O)C1=N[Si](C)(C)C	2576.7	Semi standard non polar	33892256
1-Methyladenosine,2TMS,isomer #4	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C1=N	2659.7	Semi standard non polar	33892256
1-Methyladenosine,2TMS,isomer #5	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O)C1=N[Si](C)(C)C	2597.0	Semi standard non polar	33892256
1-Methyladenosine,2TMS,isomer #6	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C)C1=N[Si](C)(C)C	2590.7	Semi standard non polar	33892256
1-Methyladenosine,3TMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C1=N	2636.1	Semi standard non polar	33892256
1-Methyladenosine,3TMS,isomer #2	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C1=N[Si](C)(C)C	2556.9	Semi standard non polar	33892256
1-Methyladenosine,3TMS,isomer #3	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C1=N[Si](C)(C)C	2561.4	Semi standard non polar	33892256
1-Methyladenosine,3TMS,isomer #4	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C1=N[Si](C)(C)C	2563.0	Semi standard non polar	33892256
1-Methyladenosine,4TMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C1=N[Si](C)(C)C	2585.9	Semi standard non polar	33892256
1-Methyladenosine,4TMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C1=N[Si](C)(C)C	2833.4	Standard non polar	33892256
1-Methyladenosine,4TMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C1=N[Si](C)(C)C	3450.4	Standard polar	33892256
1-Methyladenosine,1TBDMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C1=N	2925.1	Semi standard non polar	33892256
1-Methyladenosine,1TBDMS,isomer #2	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C1=N	2925.3	Semi standard non polar	33892256
1-Methyladenosine,1TBDMS,isomer #3	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C1=N	2918.6	Semi standard non polar	33892256
1-Methyladenosine,1TBDMS,isomer #4	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=N[Si](C)(C)C(C)(C)C	2863.6	Semi standard non polar	33892256
1-Methyladenosine,2TBDMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C1=N	3075.3	Semi standard non polar	33892256
1-Methyladenosine,2TBDMS,isomer #2	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C1=N	3067.4	Semi standard non polar	33892256
1-Methyladenosine,2TBDMS,isomer #3	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C1=N[Si](C)(C)C(C)(C)C	3025.4	Semi standard non polar	33892256
1-Methyladenosine,2TBDMS,isomer #4	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C1=N	3068.2	Semi standard non polar	33892256
1-Methyladenosine,2TBDMS,isomer #5	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C1=N[Si](C)(C)C(C)(C)C	3025.6	Semi standard non polar	33892256
1-Methyladenosine,2TBDMS,isomer #6	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C1=N[Si](C)(C)C(C)(C)C	3019.0	Semi standard non polar	33892256
1-Methyladenosine,3TBDMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C1=N	3237.3	Semi standard non polar	33892256
1-Methyladenosine,3TBDMS,isomer #2	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C1=N[Si](C)(C)C(C)(C)C	3194.5	Semi standard non polar	33892256
1-Methyladenosine,3TBDMS,isomer #3	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C1=N[Si](C)(C)C(C)(C)C	3195.9	Semi standard non polar	33892256
1-Methyladenosine,3TBDMS,isomer #4	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C1=N[Si](C)(C)C(C)(C)C	3181.4	Semi standard non polar	33892256
1-Methyladenosine,4TBDMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C1=N[Si](C)(C)C(C)(C)C	3363.8	Semi standard non polar	33892256
1-Methyladenosine,4TBDMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C1=N[Si](C)(C)C(C)(C)C	3593.4	Standard non polar	33892256
1-Methyladenosine,4TBDMS,isomer #1	CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C1=N[Si](C)(C)C(C)(C)C	3707.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1-Methyladenosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0790000000-1516313b8da901f28bba	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methyladenosine GC-EI-TOF (Non-derivatized)	splash10-0a4i-0790000000-1516313b8da901f28bba	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methyladenosine GC-EI-TOF (Non-derivatized)	splash10-0a4i-0980000000-be208cfd62e67d98bf67	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Methyladenosine GC-EI-TOF (Non-derivatized)	splash10-0uxr-0920000000-266456505e459aed90d9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyladenosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fu-9260000000-df75440994d3681767ba	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyladenosine GC-MS (3 TMS) - 70eV, Positive	splash10-001i-7351900000-778aa9d9e15b6acad19d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyladenosine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0uf0-0990000000-d2a48b28d5d54fab5f15	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0udi-0900000000-1510e824c4b3bc404014	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0udi-0900000000-59193e9776c5cc704743	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-001i-0190000000-4ba89d6b5f6346f13785	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-0udi-0910000000-75e5e157192c62256edd	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-0udi-0900000000-f51a7adbe93284cc633f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-0udi-0900000000-2bcab3f498a3a7f4963c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-0udi-0900000000-7976b81cb29dc82fb60b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0udi-0900000000-3df081c89b3bc3d51542	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-06si-1900000000-a81173c3e117179fcf34	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine Linear Ion Trap , negative-QTOF	splash10-0002-0900000000-ada4e622e88814c85e19	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine Linear Ion Trap , negative-QTOF	splash10-0002-0900000000-943dbe2cb7ab7a16983c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine Linear Ion Trap , negative-QTOF	splash10-0012-0690000000-7ded552a1e7600aa85a2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine Linear Ion Trap , negative-QTOF	splash10-000t-0590000000-baf52d13e2aba197228a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine Linear Ion Trap , negative-QTOF	splash10-001i-0090000000-6488105a96116c2e7d3e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine Linear Ion Trap , negative-QTOF	splash10-001i-0090000000-9bbdc90acacfdb29c608	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine LC-ESI-QQ , positive-QTOF	splash10-001i-0190000000-4ba89d6b5f6346f13785	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine LC-ESI-QQ , positive-QTOF	splash10-0udi-0910000000-75e5e157192c62256edd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-Methyladenosine LC-ESI-QQ , positive-QTOF	splash10-0udi-0900000000-f51a7adbe93284cc633f	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenosine 10V, Positive-QTOF	splash10-0udi-0940000000-7bf78ed8c7e7d0a7aaef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenosine 20V, Positive-QTOF	splash10-0udi-0900000000-111942c283b07a7fbe9b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenosine 40V, Positive-QTOF	splash10-0udl-4900000000-3e1b66adc79286880543	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenosine 10V, Negative-QTOF	splash10-001j-0690000000-014387065eec31451d4c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenosine 20V, Negative-QTOF	splash10-0002-0900000000-cd5b6cd7bfcdf3c8a1ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyladenosine 40V, Negative-QTOF	splash10-053r-0900000000-1caa586963ed5992f3e3	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Breast Milk
Feces
Urine

Tissue Locations

Placenta
Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.10 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	7482520	details
Blood	Detected and Quantified	0.0609 +/- 0.0181 uM	Adult (>18 years old)	Both	Normal	12675874	details
Breast Milk	Detected and Quantified	0.34 +/- 0.07 uM	Adult (>18 years old)	Female	Normal	7702711	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	19010317	details
Urine	Detected and Quantified	5.96 (0.00-12.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15116424	details
Urine	Detected and Quantified	2.37 +/- 0.37 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9129323	details
Urine	Detected and Quantified	2.03 +/- 0.20 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	9129323	details
Urine	Detected and Quantified	2.19 +/- 0.33 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9129323	details
Urine	Detected and Quantified	18.0 +/- 1.0 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	7482520	details
Urine	Detected and Quantified	1.7 (0.9-3.6) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.078 +/- 0.031 uM	Adult (>18 years old)	Both	Leukemia	7482520	details
Blood	Detected and Quantified	0.0860 +/- 0.0095 uM	Adult (>18 years old)	Female	Ovarian cancer	7482520	details
Blood	Detected and Quantified	0.370 +/- 0.050 uM	Adult (>18 years old)	Both	Uremia	9607216	details
Blood	Detected and Quantified	0.105 +/- 0.036 uM	Adult (>18 years old)	Both	Stomach cancer	7482520	details
Blood	Detected and Quantified	0.096 +/- 0.095 uM	Adult (>18 years old)	Both	Hepatocellular cancer	7482520	details
Blood	Detected and Quantified	0.094 +/- 0.063 uM	Adult (>18 years old)	Both	Cholangioma cancer	7482520	details
Blood	Detected and Quantified	0.134 +/- 0.111 uM	Adult (>18 years old)	Both	Colon cancer	7482520	details
Blood	Detected and Quantified	0.150 +/- 0.010 uM	Adult (>18 years old)	Both	Uremia	9607216	details
Blood	Detected and Quantified	0.220 +/- 0.430 uM	Adult (>18 years old)	Both	Kidney disease	9607216	details
Blood	Detected and Quantified	0.310 +/- 0.010 uM	Adult (>18 years old)	Both	Uremia	9607216	details
Blood	Detected and Quantified	0.370 +/- 0.200 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Blood	Detected and Quantified	0.145 uM	Adult (>18 years old)	Female	Cervical cancer	7482520	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Ovarian cancer	19010317	details
Urine	Detected and Quantified	4.7 +/- 1.3 umol/mmol creatinine	Adult (>18 years old)	Both	Uremia	7482520	details

Associated Disorders and Diseases

Disease References

Leukemia
Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
Ovarian cancer
Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ] Woo HM, Kim KM, Choi MH, Jung BH, Lee J, Kong G, Nam SJ, Kim S, Bai SW, Chung BC: Mass spectrometry based metabolomic approaches in urinary biomarker study of women's cancers. Clin Chim Acta. 2009 Feb;400(1-2):63-9. doi: 10.1016/j.cca.2008.10.014. Epub 2008 Oct 30. [PubMed:19010317 ]
Uremia
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 ] Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ] Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Kidney disease
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 ]
Stomach cancer
Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
Hepatocellular carcinoma
Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
Cholangiocarcinoma
Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
Colorectal cancer
Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Cervical cancer
Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]

Associated OMIM IDs

167000 (Ovarian cancer)
137215 (Stomach cancer)
114550 (Hepatocellular carcinoma)
114500 (Colorectal cancer)
603956 (Cervical cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000419

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]
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 1-Methyladenosine (HMDB0003331)

MOL for HMDB0003331 (1-Methyladenosine)

3D MOL for HMDB0003331 (1-Methyladenosine)

3D SDF for HMDB0003331 (1-Methyladenosine)

3D-SDF for HMDB0003331 (1-Methyladenosine)

PDB for HMDB0003331 (1-Methyladenosine)

3D PDB for HMDB0003331 (1-Methyladenosine)

SMILES for HMDB0003331 (1-Methyladenosine)

INCHI for HMDB0003331 (1-Methyladenosine)

Structure for HMDB0003331 (1-Methyladenosine)

3D Structure for HMDB0003331 (1-Methyladenosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra