Summary

Full name2,8-dimethyladenosine
IUPAC name(2R,3R,4S,5R)-2-(6-amino-2,8-dimethylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Short namem2,8A
MODOMICS code28A
Synonyms
2,8-dimethyladenosine
(2R,3R,4S,5R)-2-(6-Amino-2,8-dimethyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
(2R,3R,4S,5R)-2-(6-amino-2,8-dimethylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
63954-66-5
SCHEMBL18740403

Nature of the modified residueNatural
RNAMods code±
Residue unique ID136
Found in RNAYes
Related nucleotides371
Enzymes Cfr (Staphylococcus sciuri)
Found in phylogenyEubacteria
Found naturally in RNA typesrRNA

Chemical information

Sum formulaC12H17N5O4
Type of moietynucleoside
Degeneracynot applicable
SMILESCc1nc2c(N)nc(C)nc2[n]1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
logP-0.782
TPSA139.54
Number of atoms21
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/C12H17N5O4/c1-4-14-10(13)7-11(15-4)17(5(2)16-7)12-9(20)8(19)6(3-18)21-12/h6,8-9,12,18-20H,3H2,1-2H3,(H2,13,14,15)/t6-,8-,9-,12-/m1/s1
InChIKeyFGMBEEFIKCGALL-WOUKDFQISA-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)nc(C)nc2n1C3OC(CO)C(O)C3O tautomer #0
Cc1nc2c(N)nc(C)nc2n1C3OC(CO)C(O)C3O tautomer #1
C=C1Nc2c(N)nc(C)nc2N1C3OC(CO)C(O)C3O tautomer #2
Cc1nc2c(=N)nc(C)[nH]c2n1C3OC(CO)C(O)C3O tautomer #3
Cc1nc2=C(N)NC(=C)N=c2n1C3OC(CO)C(O)C3O tautomer #4
Cc1nc2C(=N)NC(=C)Nc2n1C3OC(CO)C(O)C3O tautomer #5
C=C1Nc2c(N)nc(C)nc2N1C3OC(CO)C(O)C3O tautomer #6
Cc1nc2c(=N)[nH]c(C)nc2n1C3OC(CO)C(O)C3O tautomer #7
Cc1nc2C(N)=NC(=C)Nc2n1C3OC(CO)C(O)C3O tautomer #8
CC1=NC2C(=N)N=C(C)N=C2N1C3OC(CO)C(O)C3O tautomer #9
C=C1N=C2C(=N)N=C(C)NC2N1C3OC(CO)C(O)C3O tautomer #10
C=c1nc2C(N)N=C(C)N=c2n1C3OC(CO)C(O)C3O tautomer #11
CC1=NC2C(=N)NC(=C)N=C2N1C3OC(CO)C(O)C3O tautomer #12
C=C1NC2C(=N)N=C(C)N=C2N1C3OC(CO)C(O)C3O tautomer #13
C=C1NC2C(=N)NC(=C)N=C2N1C3OC(CO)C(O)C3O tautomer #14
C=c1nc2C(N)NC(=C)N=c2n1C3OC(CO)C(O)C3O tautomer #15
C=C1N=C2C(=N)NC(=C)NC2N1C3OC(CO)C(O)C3O tautomer #16
C=C1Nc2c(=N)nc(C)[nH]c2N1C3OC(CO)C(O)C3O tautomer #17
C=C1N=C2C(N)=NC(C)=NC2N1C3OC(CO)C(O)C3O tautomer #18
C=C1N=C2C(=N)NC(C)=NC2N1C3OC(CO)C(O)C3O tautomer #19
CC1=NC2C(N)=NC(=C)N=C2N1C3OC(CO)C(O)C3O tautomer #20
C=C1NC2=C(N)NC(=C)N=C2N1C3OC(CO)C(O)C3O tautomer #21
C=C1NC=2C(=N)NC(=C)NC2N1C3OC(CO)C(O)C3O tautomer #22
C=C1NC2C(N)=NC(=C)N=C2N1C3OC(CO)C(O)C3O tautomer #23
C=C1N=C2C(N)=NC(=C)NC2N1C3OC(CO)C(O)C3O tautomer #24
C=C1Nc2c(=N)[nH]c(C)nc2N1C3OC(CO)C(O)C3O tautomer #25
C=C1NC=2C(N)=NC(=C)NC2N1C3OC(CO)C(O)C3O tautomer #26

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m2,8A m2,8A m2,8A

* 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 mass295.1281
Average mass295.294
[M+H]+296.1358
Product ions164
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.

Chemical groups contained

TypeSubtype
methyl groupmethyl group

Reactions producing 2,8-dimethyladenosine

Name
m2A:m2,8A
m8A:m2,8A

Publications

Title Authors Journal Details PubMed Id DOI
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 [details] 19144912 -

Last modification of this entry: Sept. 29, 2021


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