Summary

Full nameN6-glycinylcarbamoyladenosine
IUPAC name2-[[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]carbamoylamino]acetic acid
Short nameg6A
MODOMICS code65A
Synonyms
2-(3-(9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)ureido)acetic acid
29902-55-4

Nature of the modified residueNatural
RNAMods code
Residue unique ID114
Found in RNAYes
Related nucleotides435

Chemical information

Sum formulaC13H16N6O7
Type of moietynucleoside
Degeneracynot applicable
SMILESOC(CNC(Nc1ncnc2c1nc[n]2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)=O)=O
logP-1.8922
TPSA191.95
Number of atoms26
Number of Hydrogen Bond Acceptors 1 (HBA1)12
Number of Hydrogen Bond Acceptors 2 (HBA2)13
Number of Hydrogen Bond Donors (HBD)6
PDB no exac match , link to the most similar ligand AET
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0041623
InChIInChI=1S/C13H16N6O7/c20-2-5-8(23)9(24)12(26-5)19-4-17-7-10(15-3-16-11(7)19)18-13(25)14-1-6(21)22/h3-5,8-9,12,20,23-24H,1-2H2,(H,21,22)(H2,14,15,16,18,25)/t5-,8-,9-,12-/m1/s1
InChIKeyAHESNRWOMYGILC-JJNLEZRASA-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
O=C(CNC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #0
OC(C=NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #1
O=C(CNC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #2
OC(C=NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #3
O=C(CNC(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #4
OC(C=NC(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #5
O=C(CNC(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #6
OC(C=NC(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #7
OC(=CNC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #8
O=C(CN=C(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #9
OC(=CNC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #10
O=C(CN=C(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #11
O=C(CNC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #12
OC(C=NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #13
O=C(CNC(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)=O)O tautomer #14
OC(C=NC(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)=O)O tautomer #15
O=C(CNC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #16
OC(C=NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #17
OC(=CNC(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #18
O=C(CN=C(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #19
OC(=CNC(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)=O)O tautomer #20
O=C(CN=C(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #21
OC(=CN=C(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #22
OC(=CN=C(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #23
OC(=CNC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #24
OC(=CNC(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)=O)O tautomer #25
O=C(CN=C(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)O)O tautomer #26
OC(=CNC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #27
OC(=CN=C(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #28
OC(=CN=C(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)O)O tautomer #29
OC(=CN=C(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)O)O tautomer #30

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
g6A g6A g6A

* 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 mass368.108
Average mass368.302
[M+H]+369.1158
Product ions237
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

g6A was isolated from bulk yeast tRNA

Chemical groups contained

TypeSubtype
aminoacyl groupglycyl
othercarbamoyl

Reactions producing N6-glycinylcarbamoyladenosine

Name
A:g6A

Publications

Title Authors Journal Details PubMed Id DOI
The isolation and characterization of N-[9-(beta-D-ribofuranosyl)-purin-6-ylcarbamoyl]glycine from yeast transfer RNA. Schweizer MP, McGrath K, Baczynskyj L... Biochem Biophys Res Commun [details] 5503779 -

Last modification of this entry: Sept. 29, 2021


Copyright © Genesilico - All rights reserved
If you have any advice or suggestions for corrections or improvements, please contact: Andrea Cappannini - lp.vog.bcmii@ininnappaca