Summary

Full nameN7-methyl-guanosine cap (cap 0)
Short namem7GpppN
MODOMICS code79553N
Nature of the modified residueNatural
RNAMods code©
Residue unique ID132
Found in RNAYes
Enzymes Abd1 (Saccharomyces cerevisiae)
Hcm1 (Homo sapiens)
Found in phylogenyEukaryota
Found naturally in RNA typesmRNA, snRNA

Chemical information

Sum formulaC16H23N5O17P3
Type of moietynucleotide
Degeneracyunspecified residue
SMILESC[n+]1c[n]([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)c2c1c(nc(N)[nH]2)=O.[*]%91
logP-1.5702
TPSA366.7
Number of atoms42
Number of Hydrogen Bond Acceptors 1 (HBA1)17
Number of Hydrogen Bond Acceptors 2 (HBA2)20
Number of Hydrogen Bond Donors (HBD)6
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
C[n+]1cn(C2OC(COP([O-])(OP([O-])(OP([O-])(OCC3OC(C(O)C3O)*)=O)=O)=O)C(O)C2O)c4c1c([nH]c(=N)[nH]4)=O tautomer #0
C[n+]1cn(C2OC(COP([O-])(OP([O-])(OP([O-])(OCC3OC(C(O)C3O)*)=O)=O)=O)C(O)C2O)c4c1c([nH]c(N)n4)=O tautomer #1
C[n+]1cn(C2OC(COP([O-])(OP([O-])(OP([O-])(OCC3OC(C(O)C3O)*)=O)=O)=O)C(O)C2O)c4c1c(nc(N)n4)O tautomer #2
C[n+]1cn(C2OC(COP([O-])(OP([O-])(OP([O-])(OCC3OC(C(O)C3O)*)=O)=O)=O)C(O)C2O)c4c1c(nc(N)[nH]4)=O tautomer #3
C[n+]1cn(C2OC(COP([O-])(OP([O-])(OP([O-])(OCC3OC(C(O)C3O)*)=O)=O)=O)C(O)C2O)c4c1c([nH]c(=N)n4)O tautomer #4
C[n+]1cn(C2OC(COP([O-])(OP([O-])(OP([O-])(OCC3OC(C(O)C3O)*)=O)=O)=O)C(O)C2O)c4c1c(nc(N)n4)O tautomer #5
C[N+]1=CN(C2OC(COP([O-])(OP([O-])(OP([O-])(OCC3OC(C(O)C3O)*)=O)=O)=O)C(O)C2O)C=4C1C(NC(=N)N4)=O tautomer #6
C[n+]1cn(C2OC(COP([O-])(OP([O-])(OP([O-])(OCC3OC(C(O)C3O)*)=O)=O)=O)C(O)C2O)c4c1c(nc(=N)[nH]4)O tautomer #7
C[N+]1=CN(C2OC(COP([O-])(OP([O-])(OP([O-])(OCC3OC(C(O)C3O)*)=O)=O)=O)C(O)C2O)C=4C1C(N=C(N)N4)=O tautomer #8
C[N+]1=CN(C2OC(COP([O-])(OP([O-])(OP([O-])(OCC3OC(C(O)C3O)*)=O)=O)=O)C(O)C2O)C=4C1C(=NC(=N)N4)O tautomer #9

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m7GpppN m7GpppN m7GpppN

* 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 mass455.0243
Average mass650.298
[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

wikipedia: The 5' cap is found on the 5' end of an mRNA molecule and consists of a guanine nucleotide connected to the mRNA via an unusual 5' to 5' triphosphate linkage. This guanosine is methylated on the 7 position directly after capping in vitro by a methyl transferase. It is referred to as a 7-methylguanosine cap, abbreviated m7G. Most properties, save the triphosphate linkage, are the same as any other 7-methylguanosine.

Chemical groups contained

TypeSubtype
methyl groupmethyl group

Reactions producing N7-methyl-guanosine cap (cap 0)

Name
GpppN:m7GpppN

Reactions starting from N7-methyl-guanosine cap (cap 0)

Name
m7GpppN:m2,7GpppN
m7GpppN:m7GpppNm
m7GpppN:m7GpppNNm

Last modification of this entry: Sept. 29, 2021


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