Summary

Full name2'-O-methyladenosine
IUPAC name(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
Short nameAm
MODOMICS code0A
Synonyms
02YX82IHZ5
0883AB
140M796
2140-79-6
21919-04-0
2'-O-Me-A
2'-O-Methyl adenosine
2-O-Methyladenosine
2''-O-Methyladenosine
2'-O-Methyladenosine
2/'-O-Methyladenosine
2'-O-METHYL-ADENOSINE
2'-O-Methyladenosine, 99% - 1G 1g
2'-O-Methyl-D-adenosine
(2R,3R,4R,5R)-2-Hydroxymethyl-4-methoxy-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-ol
(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxy-tetrahydrofuran-3-ol
(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxytetrahydrofuran-3-ol
(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-hydroxymethyl-4-methoxy-tetrahydro-furan-3-ol
(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxy-tetrahydrofuran-3-ol
5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
AC1L2SDS
AC1Q4Y1K
AC-8216
Adenosine, 2'-O-methyl-
AJ-45572
AKOS016003815
AN-8216
ANW-64052
AR-1H6600
BCP17411
BDBM50144945
C11H15N5O4
CHEBI:69426
CHEMBL73237
CID102213
cordysinin B
CS-W012268
CTK1A7124
DS-14586
DTXSID50175671
FPUGCISOLXNPPC-IOSLPCCCSA-N
HG1274
HY-W011552
K-6125
MFCD00056002
NS00015020
NSC249005
PDSP1_001054
PDSP2_001038
Q63392855
SC-43502
SCHEMBL25936
ST24033989
TC-152797
UNII-02YX82IHZ5
ZINC3776540

Nature of the modified residueNatural
RNAMods code:
Residue unique ID127
Found in RNAYes
Related nucleotides207
Enzymes Nop1 (Saccharomyces cerevisiae)
Nsr (Streptomyces actuosus)
Trm13 (Saccharomyces cerevisiae)
Tsr (Streptomyces cyaneus)
Found in phylogenyEubacteria, Eukaryota
Found naturally in RNA typesrRNA, snRNA, snoRNA, tRNA

Chemical information

Sum formulaC11H15N5O4
Type of moietynucleoside
Degeneracynot applicable
SMILESCO[C@H]1[C@H]([n]2cnc3c2ncnc3N)O[C@H](CO)[C@H]1O
logP-0.7447
TPSA128.54
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)3
PDB no exac match , link to the most similar ligand ADN
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0004326
InChIInChI=1S/C11H15N5O4/c1-19-8-7(18)5(2-17)20-11(8)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
InChIKeyFPUGCISOLXNPPC-IOSLPCCCSA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs
3718406
10232470
14848749
44432150
47510072
47731265
50748516
57337604
103273217
103810807
104033932
104366301
117523226
123391720
126617341
126664467
127882065
135059797
143236561
160712543
160831550
162501500
163842727
164216520
164229145
185986641
198983362
204407415
223554743
223664198
224905493
226413909
249853643
250013515
250200715
251880273
252219132
252256270
252400670
252410165
252462259
255419788
257070213
275186961
275876016
297448343
307080790
310276482
312226775
313189001
315442303
315736070
316538426
316900027
316967514
318048550
321933321
322091931
341155830
341840994
342465014
342580353
346692831
347797543
348902071
355102237
355215591
363671138
374042396
375229558
375322431
375567437
375611442
375668554
375934562
376048183
376131880
377991368
381022575
383218808
383533426
384429098
385633762
386627935
387090666
403060256
404759670
404825310
405021342
406587954
406671931
419542042
433711929
433775048
433775443
433814709
434694282
438515881
440820913
441087806
441394050
442064918
443519724

* 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
COC1C(n2cnc3c2ncnc3N)OC(CO)C1O tautomer #0
COC1C(n2cnc3c2ncnc3N)OC(CO)C1O tautomer #1
COC1C(n2cnc3c2[nH]cnc3=N)OC(CO)C1O tautomer #2
COC1C(n2cnc3c2nc[nH]c3=N)OC(CO)C1O tautomer #3
COC1C(N2C=NC3C2=NC=NC3=N)OC(CO)C1O tautomer #4

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
Am Am Am

* 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]+282.1195
Product ions136
Normalized LC elution time *1,59 (Kellner 2014); 1,83 (Kellner 2014)
LC elution order/characteristicsbetween A and m6A (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 -
Quantitative analysis of ribonucleoside modifications in tRNA by HPLC-coupled mass spectrometry. Su D, Chan CT, Gu C, Lim KS, Chionh YH, McBee ME, Russell BS, Babu IR, Begley TJ, Dedon PC... Nat Protoc [details] 24625781 -
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 O2

Reactions producing 2'-O-methyladenosine

Name
A:Am

Reactions starting from 2'-O-methyladenosine

Name
Am:m6Am
Am:Im
Am:m1Am

Last modification of this entry: Sept. 29, 2021


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