Summary

Full name8-methyladenosine
IUPAC name(2R,3R,4S,5R)-2-(6-amino-8-methylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Short namem8A
MODOMICS code8A
Synonyms
2-(6-Amino-8-methyl-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
(2R,3R,4S,5R)-2-(6-Amino-8-methyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
(2R,3R,4S,5R)-2-(6-amino-8-methylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
(2R,3R,4S,5R)-2-(6-amino-8-methyl-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
56973-12-7
8-Methyl adenosine
8-Methyl Ado
8-Methyladenosine
AC1L57Q5
Adenosine, 8-methyl-
Adenosine, 8-methyl-(9CI)
CID171555
CTK5A6087
DTXSID40205572
RTGYRFMTJZYXPD-IOSLPCCCSA-N
SCHEMBL967122
ZINC5161492

Nature of the modified residueNatural
RNAMods codeâ
Residue unique ID131
Found in RNAYes
Related nucleotides410
Enzymes Cfr (Staphylococcus sciuri)
Found in phylogenyEubacteria
Found naturally in RNA typesrRNA

Chemical information

Sum formulaC11H15N5O4
Type of moietynucleoside
Degeneracynot applicable
SMILESCc1nc2c(N)ncnc2[n]1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
logP-1.0904
TPSA139.54
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)4
PDB no exac match , link to the most similar ligand N8M
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0000050
InChIInChI=1S/C11H15N5O4/c1-4-15-6-9(12)13-3-14-10(6)16(4)11-8(19)7(18)5(2-17)20-11/h3,5,7-8,11,17-19H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
InChIKeyRTGYRFMTJZYXPD-IOSLPCCCSA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs

* 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
Cc1nc2c(N)ncnc2n1C3OC(CO)C(O)C3O tautomer #0
Cc1nc2c(N)ncnc2n1C3OC(CO)C(O)C3O tautomer #1
C=C1Nc2c(N)ncnc2N1C3OC(CO)C(O)C3O tautomer #2
C=C1Nc2c(N)ncnc2N1C3OC(CO)C(O)C3O tautomer #3
Cc1nc2c(=N)nc[nH]c2n1C3OC(CO)C(O)C3O tautomer #4
Cc1nc2c(=N)[nH]cnc2n1C3OC(CO)C(O)C3O tautomer #5
CC1=NC2C(=N)N=CN=C2N1C3OC(CO)C(O)C3O tautomer #6
C=c1nc2C(N)N=CN=c2n1C3OC(CO)C(O)C3O tautomer #7
C=C1N=C2C(N)=NC=NC2N1C3OC(CO)C(O)C3O tautomer #8
C=C1NC2C(=N)N=CN=C2N1C3OC(CO)C(O)C3O tautomer #9
C=C1N=C2C(=N)N=CNC2N1C3OC(CO)C(O)C3O tautomer #10
C=C1N=C2C(=N)NC=NC2N1C3OC(CO)C(O)C3O tautomer #11
C=C1Nc2c(=N)nc[nH]c2N1C3OC(CO)C(O)C3O tautomer #12
C=C1Nc2c(=N)[nH]cnc2N1C3OC(CO)C(O)C3O tautomer #13

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m8A m8A m8A

* 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 * not available
LC elution order/characteristics not available

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

Comments

The methyltransferase Cfr making m8A, has only been found in Staphylococcus sciuri so far, but it has been investigated in E. coli by expression of Cfr from a plasmid coded gene. It methylates A2503 in E. coli 23S RNA to m8A.

Also see: Identification of 8-methyladenosine as the modification catalyzed by the radical SAM methyltransferase Cfr that confers antibiotic resistance in bacteria. Giessing AM, Jensen SS, Rasmussen A, Hansen LH, Gondela A, Long K, Vester B, Kirpekar F. RNA. 2009 Feb;15(2):327-36.
PMID: 19144912

Chemical groups contained

TypeSubtype
methyl groupmethyl at aromatic C

Reactions producing 8-methyladenosine

Name
A:m8A

Reactions starting from 8-methyladenosine

Name
m8A:m2,8A

Last modification of this entry: Sept. 29, 2021


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