Summary

Full nameN6-methyladenosine
IUPAC name(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)purin-9-yl]oxolane-3,4-diol
Short namem6A
MODOMICS code6A
Synonyms
1867-73-8
2575AH
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)-9H-purin-9-yl]oxolane-3,4-diol
(2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)purin-9-yl]oxolane-3,4-diol
(2R,3S,4R,5R)-2-Hydroxymethyl-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3,4-diol
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)purin-9-yl]tetrahydrofuran-3,4-diol
4rdn
(4S,2R,3R,5R)-5-(hydroxymethyl)-2-[6-(methylamino)purin-9-yl]oxolane-3,4-diol
56860-12-9
60209-41-8
6MD
6-Methyladenosine
6-methylamino-9-beta-delta-ribofuranosyl-Purine
6-methylamino-9-beta-D-ribofuranosyl-Purine
6-Methylaminopurine 9-ribofuranoside
6-Methylaminopurine arabinoside
6-Methylaminopurine D-riboside
6-Methylaminopurine ribonucleoside
6-Methylaminopurine riboside
6-Methylaminopurinosine
6MZ
AC1L2SAS
AC1Q4Y57
Adenosine, N-methyl-
Adenosine, N-methyl- (8CI)
Adenosine, N-methyl- (8CI)(9CI)
AJ-49684
AKOS024260287
AR-1K7612
Ara-map
BDBM50163023
BPBio1_000413
BRD-K81807412-001-03-1
BSPBio_000375
C010223
C11-H15-N5-O4
C11H15N5O4
CCG-220338
CHEBI:21891
CHEMBL383144
CID102175
CLE6G00625
CS-3285
CTK0H6388
DTXSID6020858
Epitope ID:140951
GS-6701
HMS1569C17
HMS2096C17
HMS2234N05
HMS3713C17
HY-N0086
J-700317
LS-7512
M6A
MFCD00005739
MLS002153780
N6 -methyladenosine
N(6)mAdo
N6-Methyladenosine
(N-6)-Methyladenosine
N(6)-Methyladenosine
N6-methyladenosine (m6A)
N6-METHYLADENOSINE-5'-MONOPHOSPHATE
N(6)-monomethyladenosine
N/A
NCGC00162241-01
NCGC00162241-02
NCGC00162241-04
N-methyl-9-alpha-L-ribofuranosyl-9H-purin-6-amine
N-methyl-9-beta-L-ribofuranosyl-9H-purin-6-amine
N-Methyladenosine
NSC 29409
NSC-29409
NSC627045
PDSP1_001030
PDSP2_001014
Prestwick0_000338
Prestwick1_000338
Prestwick2_000338
Prestwick3_000338
Prestwick_343
Purine, 6-methylamino-9-beta-D-ribofuranosyl-
Q6951996
s3190
SB34650
SCHEMBL40634
SMR001233164
SPBio_002296
ST24034024
ST50412061
SW196617-3
UNII-CLE6G00625
VQAYFKKCNSOZKM-IOSLPCCCSA-N
ZINC4245632

Nature of the modified residueNatural
RNAMods code=
Residue unique ID96
Found in RNAYes
Related nucleotides211
Enzymes ErmAM (Streptococcus pneumoniae)
ErmBC (Escherichia coli)
ErmC' (Bacillus subtilis)
Ime4 (Saccharomyces cerevisiae)
METTL14 (Homo sapiens)
METTL3 (Homo sapiens)
RlmF (Escherichia coli)
RlmJ (Escherichia coli)
RsmA (Escherichia coli)
RsmA (Saccharomyces cerevisiae)
RsmA (Thermus thermophilus)
TrmM (Escherichia coli)
Found in phylogenyEubacteria, Eukaryota
Found naturally in RNA typesmRNA, rRNA, snRNA, tRNA

Chemical information

Sum formulaC11H15N5O4
Type of moietynucleoside
Degeneracynot applicable
SMILESCNc1ncnc2c1nc[n]2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
logP-1.4475
TPSA125.55
Number of atoms20
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)9
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand 26A
PDB exact match , link to the most similar ligand 6MD
HMDB (Human Metabolome Database) exact match HMDB0004044
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0004044
InChIInChI=1S/C11H15N5O4/c1-12-9-6-10(14-3-13-9)16(4-15-6)11-8(19)7(18)5(2-17)20-11/h3-5,7-8,11,17-19H,2H2,1H3,(H,12,13,14)/t5-,7-,8-,11-/m1/s1
InChIKeyVQAYFKKCNSOZKM-IOSLPCCCSA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs
610343
10232449
10321397
11466366
11467486
11486032
14948147
26755696
44432113
47277017
47277018
47722018
47945233
47945234
48395295
48414024
49698441
49857491
50111135
56463596
57337592
75819414
85788565
90341060
91664110
92125341
99361287
103465724
103841811
103913892
104049116
104366193
117523357
121363012
124800981
129510675
135059013
143512284
162222838
163305156
164348536
175442868
175611811
179149035
198963412
210280218
210282197
219814898
223367133
223558855
225014593
226425834
249759715
249853677
250221031
252228356
252354299
252400671
252409863
252472624
254760242
255489083
257201966
273528769
275970602
300402244
307089084
310263639
312226712
312343951
312596586
315671796
317223298
318126701
319135310
319135311
319463399
319554070
322059445
329863129
335989088
340086221
341092876
341249656
342526849
346747515
347913825
348276217
348397657
348415869
348858750
354928198
355038406
363671180
363709117
374039010
375133710
375197711
375230858
375388879
375577949
376141807
376219972
377309463
381323884
381388274
383231994
384405287
384408009
384649744
385639907
386634127
388809507
404759669
404824977
405515336
405534153
406525174
406840185
419508927
433775047
433775437
434299526
434697141
436395709
438461872
438515947
439430653
439592305
439593420
439593422
439593424
439782547
441297737
442031009
443519705

* Chemical properties calculated with Open Babel - O'Boyle et al. Open Babel: An open chemical toolbox. J Cheminform 3, 33 (2011) (link)


Download Structures

2D   .png .mol .mol2 .sdf .pdb .smi
3D   .mol .mol2 .sdf .pdb

Tautomers

Tautomers SMILES
CNc1ncnc2c1ncn2C3OC(CO)C(O)C3O tautomer #0
CNc1ncnc2c1ncn2C3OC(CO)C(O)C3O tautomer #1
CN=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O tautomer #2
CN=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O tautomer #3
CN=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O tautomer #4

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m6A m6A m6A

* CYP Metabolic sites predicted with SMARTCyp. SMARTCyp is a method for prediction of which sites in a molecule that are most liable to metabolism by Cytochrome P450. It has been shown to be applicable to metabolism by the isoforms 1A2, 2A6, 2B6, 2C8, 2C19, 2E1, and 3A4 (CYP3A4), and specific models for the isoform 2C9 (CYP2C9) and isoform 2D6 (CYP2D6). CYP3A4, CYP2D6, and CYP2C9 are the three of the most important enzymes in drug metabolism since they are involved in the metabolism of more than half of the drugs used today. The three top-ranked atoms are highlighted. See: SmartCYP and SmartCYP - background; Patrik Rydberg, David E. Gloriam, Lars Olsen, The SMARTCyp cytochrome P450 metabolism prediction server, Bioinformatics, Volume 26, Issue 23, 1 December 2010, Pages 2988–2989 (link)


LC-MS Information

Monoisotopic mass281.1124
Average mass281.268
[M+H]+282.1202
Product ions150
Normalized LC elution time *1,66 (Kellner 2014); 1,97 (Kellner 2014)
LC elution order/characteristicsafter A (Kellner 2014, Kellner 2014)

* normalized to guanosine (G), measured with a RP C-18 column with acetonitrile/ammonium acetate as mobile phase.


LC-MS Publications

Title Authors Journal Details PubMed Id DOI
Profiling of RNA modifications by multiplexed stable isotope labelling. Kellner S, Neumann J, Rosenkranz D, Lebedeva S, Ketting RF, Zischler H, Schneider D, Helm M. Chem Commun (Camb). [details] 24567952 -
Absolute and relative quantification of RNA modifications via biosynthetic isotopomers. Kellner S, Ochel A, Thuring K, Spenkuch F, Neumann J, Sharma S, Entian KD, Schneider D, Helm M... Nucleic Acids Res [details] 25129236 -

Chemical groups contained

TypeSubtype
methyl groupmethyl at other N

Reactions producing N6-methyladenosine

Name
A:m6A

Reactions starting from N6-methyladenosine

Name
m6A:ms2m6A
m6A:m6,6A
m6A:m6Am
m6A:A
m6A:hm6A

Last modification of this entry: Sept. 29, 2021


Copyright © Genesilico - All rights reserved
If you have any advice or suggestions for corrections or improvements, please contact: Andrea Cappannini - lp.vog.bcmii@ininnappaca