Modomics - A Database of RNA Modifications

m2,2G
The molecule is shown in a ball-and-stick representation with the following colors for atoms :
⬤ Hydrogen (H): white ⬤ Carbon (C): gray ⬤ Oxygen (O): red ⬤ Phosphorus (P): orange ⬤ Nitrogen (N): blue ⬤ Selenium (Se): gold ⬤ Sulfur (S): yellow

Summary

Full nameN2,N2-dimethylguanosine
IUPAC name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(dimethylamino)-1H-purin-6-one
Short namem2,2G
MODOMICS code new2000000022G
MODOMICS code22G
Synonyms
0881AB
13269-19-7
2- GUANOSINE
2140-67-2
2,2-Dimethylguanosine
2-Dimethylamino-6-oxypurine riboside
2-Dimethylamino-6-oxypurineriboside
2-(dimethylamino)-9-(beta-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-one
2-(Dimethylamino)-9-pentofuranosyl-9H-purin-6-ol
2-Dimethylaminoguanosine
2-(DIMETHYLAMINO)GUANOSINE
2-Dimethylguanosine
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(dimethylamino)-1H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(dimethylamino)-3H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(dimethylamino)-6,9-dihydro-1H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(dimethylamino)-6,9-dihydro-3H-purin-6-one
9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-(dimethylamino)-1H-purin-6(9H)-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-(dimethylamino)-1H-purin-6-one
9-((2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2-(dimethylamino)-1H-purin-6(9H)-one
AC1L3P3V
AJ-53133
AKOS016009587
AR-1K2505
AS-57489
C12H17N5O5
CHEBI:19289
CID92919
CS-0061838
CTK4E6678
Dimethylguanosine
DTXSID90943957
Guanosine, N,N-dimethyl-
Guanosine,N,N-dimethyl-
HY-113137
m22g
MFCD00057049
N2-Dimethylguanosine
N2,N2-Dimethylguanosin
N2,N2-Dimethylguanosine
N(2),N(2)-Dimethylguanosine
N,N- dimethylguanosine
N,N-dimethyl-Guanosine
N,N-Dimethylguanosine
NS00099785
P7NB8Q3W0R
Q27109160
RSPURTUNRHNVGF-IOSLPCCCSA-N
SCHEMBL40775
UNII-P7NB8Q3W0R
ZINC5115341
Nature of the modified residueNatural
RNAMods codeR
Residue unique ID13
Found in RNAYes
Related nucleotides198
Enzymes Trm-G10 (Pyrococcus abyssi)
Trm1 (Saccharomyces cerevisiae)
Trm1 (Aquifex aeolicus)
Trm1 (Pyrococcus horikoshii)
Trm1 (Homo sapiens)
Found in phylogenyArchaea, Eubacteria, Eukaryota
Found naturally in RNA typesrRNA, tRNA

Chemical information

Sum formulaC12H17N5O5
Type of moietynucleoside
Degeneracynot applicable
PubChem ID601633
SMILESCN(C)c1[nH]c(=O)c2nc[n]([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1
logP-2.2029
TPSA136.73
Number of atoms22
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 GMP
HMDB (Human Metabolome Database) no exact match, link to the most similar ligand None
InChIInChI=1S/C12H17N5O5/c1-16(2)12-14-9-6(10(21)15-12)13-4-17(9)11-8(20)7(19)5(3-18)22-11/h4-5,7-8,11,18-20H,3H2,1-2H3,(H,14,15,21)/t5-,7-,8-,11-/m1/s1
InChIKeyRSPURTUNRHNVGF-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
CN(C)c1nc(O)c2ncn(C3OC(CO)C(O)C3O)c2n1 tautomer #0
CN(C)c1nc(=O)c2ncn(C3OC(CO)C(O)C3O)c2[nH]1 tautomer #1
CN(C)c1[nH]c(=O)c2ncn(C3OC(CO)C(O)C3O)c2n1 tautomer #2
CN(C)c1nc(O)c2ncn(C3OC(CO)C(O)C3O)c2n1 tautomer #3
CN(C)C1=NC(=O)C2N=CN(C3OC(CO)C(O)C3O)C2=N1 tautomer #4
Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m2,2G m2,2G m2,2G

* 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 mass311.123
Average mass311.294
[M+H]+312.1308
Product ions180
Normalized LC elution time *1,62 (Kellner 2014)
LC elution order/characteristicsbetween A and m6A (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 -

Chemical groups contained

TypeSubtype
methyl groupmethyl at other N
methyl groupsecond methyl at other N

Reactions producing N2,N2-dimethylguanosine

Name
m2G:m2,2G

Reactions starting from N2,N2-dimethylguanosine

Name
m2,2G:m2,2Gm

Last modification of this entry: Sept. 22, 2023