Summary

Full nameN2,N2,7-trimethylguanosine cap (cap TMG)
Short namem2,2,7GpppN
MODOMICS code2279553N
Nature of the modified residueNatural
RNAMods code
Residue unique ID134
Found in RNAYes
Enzymes Tgs1 (Homo sapiens)
Found in phylogenyEukaryota
Found naturally in RNA typessnRNA, snoRNA

Chemical information

Sum formulaC18H27N5O17P3
Type of moietynucleotide
Degeneracyunspecified residue
SMILESCN(C)c1nc(=O)c2c([n](c[n+]2C)[C@@H]2O[C@H](COP([O-])(OP([O-])(OP([O-])(OC[C@H]3O[C@@H]%91[C@H](O)[C@@H]3O)=O)=O)=O)[C@@H](O)[C@H]2O)[nH]1.[*]%91
logP-1.6676
TPSA343.92
Number of atoms44
Number of Hydrogen Bond Acceptors 1 (HBA1)17
Number of Hydrogen Bond Acceptors 2 (HBA2)20
Number of Hydrogen Bond Donors (HBD)5
PDB no exac match , link to the most similar ligand GTG
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0001273
InChI
InChIKey

* 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)c1[nH]c(=O)c2c(n(c[n+]2C)C3OC(COP([O-])(OP([O-])(OP([O-])(OCC4OC(C(O)C4O)*)=O)=O)=O)C(O)C3O)n1 tautomer #0
CN(C)c1nc(O)c2c(n(c[n+]2C)C3OC(COP([O-])(OP([O-])(OP([O-])(OCC4OC(C(O)C4O)*)=O)=O)=O)C(O)C3O)n1 tautomer #1
CN(C)c1nc(=O)c2c(n(c[n+]2C)C3OC(COP([O-])(OP([O-])(OP([O-])(OCC4OC(C(O)C4O)*)=O)=O)=O)C(O)C3O)[nH]1 tautomer #2
CN(C)c1nc(O)c2c(n(c[n+]2C)C3OC(COP([O-])(OP([O-])(OP([O-])(OCC4OC(C(O)C4O)*)=O)=O)=O)C(O)C3O)n1 tautomer #3
CN(C)C1=NC(=O)C2C(N(C=[N+]2C)C3OC(COP([O-])(OP([O-])(OP([O-])(OCC4OC(C(O)C4O)*)=O)=O)=O)C(O)C3O)=N1 tautomer #4

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m2,2,7GpppN m2,2,7GpppN m2,2,7GpppN

* 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 mass483.0556
Average mass678.352
[M+H]+ not available
Product ions not available
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

m2,2,7G cap is joined to the main chain via a 5'-5' linkage. Apart from sn- and snoRNAs it was found is some human selenoprotein mRNAs.

Chemical groups contained

TypeSubtype
methyl groupmethyl at aromatic N

Reactions producing N2,N2,7-trimethylguanosine cap (cap TMG)

Name
m2,7GpppN:m2,2,7GpppN

Last modification of this entry: Sept. 29, 2021


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