Summary

Full namequeuosine
IUPAC name2-amino-5-[[[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino]methyl]-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrrolo[2,3-d]pyrimidin-4-one
Short nameQ
MODOMICS code10G
Synonyms
2-amino-5-[[[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino]methyl]-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrrolo[2,3-d]pyrimidin-4-one
2-amino-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-7-(beta-D-ribofuranosyl)-1,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
4H-Pyrrolo(2,3-d)pyrimidin-4-one, 2-amino-5-(((4,5-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-1,7-dihydro-7-beta-D-ribofuranosyl-, (1S-(1alpha,4beta,5beta))-
57072-36-3
AC1L2751
C17-H23-N5-O7
C17H23N5O7
CHEBI:60193
CID42119
DTXSID50205684
nucleoside Q
Q (nucleoside)
Q425950
QQXQGKSPIMGUIZ-AEZJAUAXSA-N
Queuosine
SCHEMBL15972263

Nature of the modified residueNatural
RNAMods codeQ
Residue unique ID65
Found in RNAYes
Related nucleotides423
Enzymes QueG (Escherichia coli)
Found in phylogenyEubacteria, Eukaryota
Found naturally in RNA typestRNA

Chemical information

Sum formulaC17H23N5O7
Type of moietynucleoside
Degeneracynot applicable
SMILESNc1[nH]c(=O)c2c([n]([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)cc2CN[C@@H]2[C@@H](O)[C@@H](O)C=C2)n1
logP-2.3598
TPSA199.11
Number of atoms29
Number of Hydrogen Bond Acceptors 1 (HBA1)10
Number of Hydrogen Bond Acceptors 2 (HBA2)11
Number of Hydrogen Bond Donors (HBD)8
PDB no exac match , link to the most similar ligand 56B
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0011596
InChIInChI=1S/C17H23N5O7/c18-17-20-14-10(15(28)21-17)6(3-19-7-1-2-8(24)11(7)25)4-22(14)16-13(27)12(26)9(5-23)29-16/h1-2,4,7-9,11-13,16,19,23-27H,3,5H2,(H3,18,20,21,28)/t7-,8-,9+,11+,12+,13+,16+/m0/s1
InChIKeyQQXQGKSPIMGUIZ-AEZJAUAXSA-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
N=C1NC(O)c2c(n(C3C(O)C(O)C(CO)O3)cc2C=NC4C(O)C(O)C=C4)N1 tautomer #0
N=c1[nH]c(=O)c2c(n(C3C(O)C(O)C(CO)O3)cc2CNC4C(O)C(O)C=C4)[nH]1 tautomer #1
Nc1nc(O)c2c(n(C3C(O)C(O)C(CO)O3)cc2CNC4C(O)C(O)C=C4)n1 tautomer #2
NC1=NC(O)c2c(n(C3C(O)C(O)C(CO)O3)cc2C=NC4C(O)C(O)C=C4)N1 tautomer #3
Nc1nc(=O)c2c(n(C3C(O)C(O)C(CO)O3)cc2CNC4C(O)C(O)C=C4)[nH]1 tautomer #4
Nc1[nH]c(=O)c2c(n(C3C(O)C(O)C(CO)O3)cc2CNC4C(O)C(O)C=C4)n1 tautomer #5
N=c1[nH]c(O)c2c(n(C3C(O)C(O)C(CO)O3)cc2CNC4C(O)C(O)C=C4)n1 tautomer #6
Nc1nc(O)c2c(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)n1 tautomer #7
Nc1nc(O)c2c(N(C3C(O)C(O)C(CO)O3)CC2=CNC4C(O)C(O)C=C4)n1 tautomer #8
N=C1NC(=O)C2C(N(C3C(O)C(O)C(CO)O3)C=C2C=NC4C(O)C(O)C=C4)N1 tautomer #9
N=C1NC(=O)C=2C(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)N1 tautomer #10
N=C1NC(=O)C2C(N(C3C(O)C(O)C(CO)O3)C=C2CNC4C(O)C(O)C=C4)=N1 tautomer #11
N=C1NC(=O)C2C(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)=N1 tautomer #12
N=C1NC(O)C=2C(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)=N1 tautomer #13
N=C1NC(=O)C=2C(N(C3C(O)C(O)C(CO)O3)CC2CNC4C(O)C(O)C=C4)=N1 tautomer #14
N=c1[nH]c(=O)c2c(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)[nH]1 tautomer #15
N=C1NC(=O)C2C(N(C3C(O)C(O)C(CO)O3)CC2=CNC4C(O)C(O)C=C4)=N1 tautomer #16
N=c1[nH]c(=O)c2c(N(C3C(O)C(O)C(CO)O3)CC2=CNC4C(O)C(O)C=C4)[nH]1 tautomer #17
Nc1nc(O)c2c(n(C3C(O)C(O)C(CO)O3)cc2CNC4C(O)C(O)C=C4)n1 tautomer #18
NC1=NC(=O)C2C(N(C3C(O)C(O)C(CO)O3)C=C2C=NC4C(O)C(O)C=C4)N1 tautomer #19
NC1=NC(=O)C=2C(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)N1 tautomer #20
NC1=NC(=O)C2C(N(C3C(O)C(O)C(CO)O3)C=C2CNC4C(O)C(O)C=C4)=N1 tautomer #21
NC1=NC(=O)C2C(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)=N1 tautomer #22
NC1=NC(O)C=2C(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)=N1 tautomer #23
NC1=NC(=O)C=2C(N(C3C(O)C(O)C(CO)O3)CC2CNC4C(O)C(O)C=C4)=N1 tautomer #24
Nc1nc(=O)c2c(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)[nH]1 tautomer #25
NC1=NC(=O)C2C(N(C3C(O)C(O)C(CO)O3)CC2=CNC4C(O)C(O)C=C4)=N1 tautomer #26
N=c1nc(O)c2c(n(C3C(O)C(O)C(CO)O3)cc2CNC4C(O)C(O)C=C4)[nH]1 tautomer #27
Nc1nc(=O)c2c(N(C3C(O)C(O)C(CO)O3)CC2=CNC4C(O)C(O)C=C4)[nH]1 tautomer #28
N=C1NC(O)=C2C(N(C3C(O)C(O)C(CO)O3)C=C2C=NC4C(O)C(O)C=C4)N1 tautomer #29
N=c1[nH]c(O)c2c(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)n1 tautomer #30
N=c1[nH]c(O)c2c(N(C3C(O)C(O)C(CO)O3)CC2=CNC4C(O)C(O)C=C4)n1 tautomer #31
NC1=NC(O)=C2C(N(C3C(O)C(O)C(CO)O3)C=C2C=NC4C(O)C(O)C=C4)N1 tautomer #32
N=C1N=C(O)C2C(N(C3C(O)C(O)C(CO)O3)C=C2C=NC4C(O)C(O)C=C4)N1 tautomer #33
N=C1N=C(O)C=2C(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)N1 tautomer #34
N=C1N=C(O)C2C(N(C3C(O)C(O)C(CO)O3)C=C2CNC4C(O)C(O)C=C4)=N1 tautomer #35
N=C1N=C(O)C2C(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)=N1 tautomer #36
N=C1N=C(O)C=2C(N(C3C(O)C(O)C(CO)O3)CC2CNC4C(O)C(O)C=C4)=N1 tautomer #37
N=c1nc(O)c2c(N(C3C(O)C(O)C(CO)O3)CC2C=NC4C(O)C(O)C=C4)[nH]1 tautomer #38
N=C1N=C(O)C2C(N(C3C(O)C(O)C(CO)O3)CC2=CNC4C(O)C(O)C=C4)=N1 tautomer #39
N=c1nc(O)c2c(N(C3C(O)C(O)C(CO)O3)CC2=CNC4C(O)C(O)C=C4)[nH]1 tautomer #40

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
Q Q Q

* 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 mass409.1597
Average mass409.394
[M+H]+410.1675
Product ions295/163
Normalized LC elution time *3,40 (Kellner 2014)
LC elution order/characteristicsafter 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 -

Chemical groups contained

TypeSubtype
otherqueuosine

Reactions producing queuosine

Name
oQ:Q
Qbase:Q

Reactions starting from queuosine

Name
Q:galQ
Q:gluQ
Q:manQ
Q:Qbase

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