Summary

Full nameN6-acetyladenosine
IUPAC nameN-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]acetamide
Short nameac6A
MODOMICS code64A
Synonyms
16265-37-5
Adenosine, N-acetyl-
CTK0A9479
DTXSID70647825
n6-acetyl-adenosine
N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]acetamide
N-(9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)acetamide
N-Acetyladenosine
SCHEMBL155836

Nature of the modified residueNatural
RNAMods code
Residue unique ID125
Found in RNAYes
Related nucleotides433

Chemical information

Sum formulaC12H15N5O5
Type of moietynucleoside
Degeneracynot applicable
SMILESCC(Nc1ncnc2c1nc[n]2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)=O
logP-1.5308
TPSA142.62
Number of atoms22
Number of Hydrogen Bond Acceptors 1 (HBA1)9
Number of Hydrogen Bond Acceptors 2 (HBA2)10
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand NKV
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0004044
InChIInChI=1S/C12H15N5O5/c1-5(19)16-10-7-11(14-3-13-10)17(4-15-7)12-9(21)8(20)6(2-18)22-12/h3-4,6,8-9,12,18,20-21H,2H2,1H3,(H,13,14,16,19)/t6-,8-,9-,12-/m1/s1
InChIKeySLLVJTURCPWLTP-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
CC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O tautomer #0
CC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O tautomer #1
C=C(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O tautomer #2
CC(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O tautomer #3
C=C(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O tautomer #4
CC(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)=O tautomer #5
CC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O tautomer #6
C=C(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)O tautomer #7
CC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O tautomer #8
C=C(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)O tautomer #9
CC(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)=O tautomer #10
C=C(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)O tautomer #11

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
ac6A ac6A ac6A

* 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 mass309.1073
Average mass309.278
[M+H]+310.1151
Product ions178
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

found in bulk tRNA from Methanopyrus kandleri

Publications

Title Authors Journal Details PubMed Id DOI
N6-Acetyladenosine: a new modified nucleoside from Methanopyrus kandleri tRNA. Sauerwald A, Sitaramaiah D, McCloskey JA, Soll D, Crain PF... FEBS Lett [details] 15907485 -

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