Summary

Full namequeuine
IUPAC name2-amino-5-[[[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino]methyl]-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one
Short nameQbase
MODOMICS code10000G
Synonyms
2-amino-5-((((1s,4s,5r)-4,5-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-1,7-dihydro-4h-pyrrolo(2,3-d)pyrimidin-4-one
2-amino-5-[[[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino]methyl]-1,7-dihydropyrrolo[2,3-d]pyrimidin-4-one
2-amino-5-{[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-ylamino]methyl}-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
2-Amino-5-({[(1s,4s,5r)-4,5-Dihydroxycyclopent-2-En-1-Yl]amino}methyl)-3,7-Dihydro-4h-Pyrrolo[2,3-D]pyrimidin-4-One
4H-pyrrolo(2,3-d)pyrimidin-4-one, 2-amino-5-((((1S,4S,5R)-4,5-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-1,7-dihydro-
4H-Pyrrolo(2,3-d)pyrimidin-4-one, 2-amino-5-(((4,5-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-1,7-dihydro-, (1S-(1alpha,4beta,5beta))-
69565-92-0
72496-59-4
7-(3,4-trans-4,5-cis-dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanine
75-16-1
AC1L3G4Z
AC1Q6IB5
AR-1D8400
base Q
C01449
C12-H15-N5-O3
C12H15N5O3
CHEBI:17433
CID 114881
CID114881
DB14732
DTXSID20895854
Q Base
Q424797
queuine
Queuine Hydrochloride
SCHEMBL15972267
SCHEMBL93906
ZINC6622451

Nature of the modified residueNatural
RNAMods code
Residue unique ID105
Found in RNAYes

Chemical information

Sum formulaC12H15N5O3
Type of moietybase
Degeneracynot applicable
SMILESNC1NC(=O)c2c(c[nH]c2N=1)CN[C@@H]1[C@@H](O)[C@@H](O)C=C1
logP-0.4447
TPSA140.05
Number of atoms20
Number of Hydrogen Bond Acceptors 1 (HBA1)6
Number of Hydrogen Bond Acceptors 2 (HBA2)6
Number of Hydrogen Bond Donors (HBD)6
PDB no exac match , link to the most similar ligand QEI
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0001495
InChIInChI=1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m0/s1
InChIKeyWYROLENTHWJFLR-ACLDMZEESA-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(c[nH]c2N1)C=NC3C(O)C(O)C=C3 tautomer #0
N=c1[nH]c(=O)c2c(c[nH]c2[nH]1)CNC3C(O)C(O)C=C3 tautomer #1
NC=1NC(O)c2c(c[nH]c2N1)C=NC3C(O)C(O)C=C3 tautomer #2
Nc1nc(O)c2c(c[nH]c2n1)CNC3C(O)C(O)C=C3 tautomer #3
NC1=NC(O)c2c(c[nH]c2N1)C=NC3C(O)C(O)C=C3 tautomer #4
Nc1nc(O)c-2c(cnc2[nH]1)CNC3C(O)C(O)C=C3 tautomer #5
Nc1nc(=O)c2c(c[nH]c2[nH]1)CNC3C(O)C(O)C=C3 tautomer #6
Nc1[nH]c(O)c-2c(cnc2n1)CNC3C(O)C(O)C=C3 tautomer #7
Nc1[nH]c(=O)c2c(c[nH]c2n1)CNC3C(O)C(O)C=C3 tautomer #8
Nc1nc(O)c2C(CNc2n1)C=NC3C(O)C(O)C=C3 tautomer #9
Nc1nc(O)c2C(C=Nc2n1)CNC3C(O)C(O)C=C3 tautomer #10
Nc1nc(O)c2C(CNc2n1)=CNC3C(O)C(O)C=C3 tautomer #11
N=c1[nH]c(O)c2c(c[nH]c2n1)CNC3C(O)C(O)C=C3 tautomer #12
N=C1NC(=O)C2C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #13
N=C1NC(=O)C2=C(C=NC2N1)CNC3C(O)C(O)C=C3 tautomer #14
N=C1NC(O)C2=C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #15
N=C1NC(=O)C2=C(CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #16
N=C1NC(O)C2=C(C=NC2=N1)CNC3C(O)C(O)C=C3 tautomer #17
N=C1NC(=O)C2C(CNC2=N1)C=NC3C(O)C(O)C=C3 tautomer #18
N=C1NC(O)C2=C(CNC2=N1)C=NC3C(O)C(O)C=C3 tautomer #19
N=C1NC(=O)C2=C(CNC2=N1)CNC3C(O)C(O)C=C3 tautomer #20
NC1=NC(O)C2C(C=NC2=N1)C=NC3C(O)C(O)C=C3 tautomer #21
NC=1NC(=O)C2=C(CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #22
NC=1NC(O)C2=C(CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #23
Nc1[nH]c(=O)c2=C(CN=c2n1)CNC3C(O)C(O)C=C3 tautomer #24
NC=1NC(=O)C2=C(C=NC2N1)CNC3C(O)C(O)C=C3 tautomer #25
NC=1NC(=O)C2C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #26
NC=1NC(O)C2=C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #27
N=C1NC(=O)C2C(C=NC2=N1)CNC3C(O)C(O)C=C3 tautomer #28
N=C1NC(=O)C2C(=CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #29
N=C1NC(=O)C2C(C=NC2N1)=CNC3C(O)C(O)C=C3 tautomer #30
N=C1NC(=O)C2C(=CNC2=N1)CNC3C(O)C(O)C=C3 tautomer #31
N=C1NC(=O)C2C(CNC2=N1)=CNC3C(O)C(O)C=C3 tautomer #32
N=C1NC(O)C=2C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #33
N=c1[nH]c(=O)c2C(CNc2[nH]1)C=NC3C(O)C(O)C=C3 tautomer #34
NC1=NC(O)C2C(C=NC2=N1)=CNC3C(O)C(O)C=C3 tautomer #35
Nc1[nH]c(=O)c2C(CNc2n1)C=NC3C(O)C(O)C=C3 tautomer #36
NC=1NC(O)C=2C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #37
NC=1NC(=O)C2C(C=NC2N1)=CNC3C(O)C(O)C=C3 tautomer #38
NC1=NC(O)C2C(=CNC2=N1)C=NC3C(O)C(O)C=C3 tautomer #39
NC=1N=C(O)C2C(=CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #40
N=c1[nH]c(=O)c2C(C=Nc2[nH]1)CNC3C(O)C(O)C=C3 tautomer #41
NC1=NC(O)C2C(=CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #42
Nc1nc(O)c2=C(CN=c2n1)CNC3C(O)C(O)C=C3 tautomer #43
N=C1NC(O)C=2C(C=NC2N1)=CNC3C(O)C(O)C=C3 tautomer #44
N=c1[nH]c(=O)c2C(CNc2[nH]1)=CNC3C(O)C(O)C=C3 tautomer #45
Nc1[nH]c(=O)c2C(CNc2n1)=CNC3C(O)C(O)C=C3 tautomer #46
NC=1NC(O)C=2C(C=NC2N1)=CNC3C(O)C(O)C=C3 tautomer #47
Nc1nc(O)c2C(CNc2n1)C=NC3C(O)C(O)C=C3 tautomer #48
Nc1nc(O)c2c(c[nH]c2n1)CNC3C(O)C(O)C=C3 tautomer #49
NC1=NC(=O)C2C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #50
NC1=NC(=O)C2=C(C=NC2N1)CNC3C(O)C(O)C=C3 tautomer #51
NC1=NC(O)C2=C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #52
NC1=NC(=O)C2=C(CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #53
NC1=NC(O)C2=C(C=NC2=N1)CNC3C(O)C(O)C=C3 tautomer #54
NC1=NC(=O)C2C(CNC2=N1)C=NC3C(O)C(O)C=C3 tautomer #55
NC1=NC(O)C2=C(CNC2=N1)C=NC3C(O)C(O)C=C3 tautomer #56
NC1=NC(=O)C2=C(CNC2=N1)CNC3C(O)C(O)C=C3 tautomer #57
N=C1NC(=O)C2C(CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #58
N=C1NC(O)C2=C(CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #59
N=c1[nH]c(=O)c2=C(CN=c2[nH]1)CNC3C(O)C(O)C=C3 tautomer #60
N=C1NC(O)C2C(C=NC2=N1)C=NC3C(O)C(O)C=C3 tautomer #61
NC1=NC(=O)C2C(C=NC2=N1)CNC3C(O)C(O)C=C3 tautomer #62
Nc1nc(O)c2C(CNc2n1)=CNC3C(O)C(O)C=C3 tautomer #63
NC1=NC(=O)C2C(=CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #64
NC1=NC(=O)C2C(C=NC2N1)=CNC3C(O)C(O)C=C3 tautomer #65
NC1=NC(=O)C2C(=CNC2=N1)CNC3C(O)C(O)C=C3 tautomer #66
NC1=NC(=O)C2C(CNC2=N1)=CNC3C(O)C(O)C=C3 tautomer #67
NC1=NC(O)C=2C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #68
N=C1NC(=O)C2C(=CN=C2N1)CNC3C(O)C(O)C=C3 tautomer #69
N=C1NC(=O)C2C(CN=C2N1)=CNC3C(O)C(O)C=C3 tautomer #70
N=C1NC(O)C2C(C=NC2=N1)=CNC3C(O)C(O)C=C3 tautomer #71
N=C1NC(O)C2C(=CNC2=N1)C=NC3C(O)C(O)C=C3 tautomer #72
Nc1nc(=O)c2C(C=Nc2[nH]1)CNC3C(O)C(O)C=C3 tautomer #73
N=C1NC(O)C2C(=CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #74
Nc1nc(=O)c2C(CNc2[nH]1)C=NC3C(O)C(O)C=C3 tautomer #75
NC1=NC(O)C=2C(C=NC2N1)=CNC3C(O)C(O)C=C3 tautomer #76
Nc1nc(=O)c2C(CNc2[nH]1)=CNC3C(O)C(O)C=C3 tautomer #77
NC1=NC(=O)C2C(CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #78
NC1=NC(O)C2=C(CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #79
Nc1nc(=O)c2=C(CN=c2[nH]1)CNC3C(O)C(O)C=C3 tautomer #80
NC=1NC(=O)C2C(CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #81
Nc1[nH]c(=O)c2C(C=Nc2n1)CNC3C(O)C(O)C=C3 tautomer #82
N=c1nc(O)c2c(c[nH]c2[nH]1)CNC3C(O)C(O)C=C3 tautomer #83
NC1=NC(=O)C2C(=CN=C2N1)CNC3C(O)C(O)C=C3 tautomer #84
NC1=NC(=O)C2C(CN=C2N1)=CNC3C(O)C(O)C=C3 tautomer #85
NC=1NC(=O)C2C(=CN=C2N1)CNC3C(O)C(O)C=C3 tautomer #86
NC=1NC(=O)C2C(CN=C2N1)=CNC3C(O)C(O)C=C3 tautomer #87
NC=1NC(=O)C2C(=CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #88
NC=1NC(O)C2C(=CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #89
NC=1NC(O)=C2C(CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #90
Nc1nc(O)c2C(C=Nc2n1)CNC3C(O)C(O)C=C3 tautomer #91
N=C1NC(O)=C2C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #92
N=c1[nH]c(O)c2C(CNc2n1)C=NC3C(O)C(O)C=C3 tautomer #93
NC=1NC(O)=C2C(CN=C2N1)=CNC3C(O)C(O)C=C3 tautomer #94
NC=1NC(O)=C2C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #95
NC=1NC(O)=C2C(=CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #96
N=c1[nH]c(O)c2C(C=Nc2n1)CNC3C(O)C(O)C=C3 tautomer #97
N=C1NC(O)=C2C(C=NC2N1)=CNC3C(O)C(O)C=C3 tautomer #98
NC=1NC(O)=C2C(C=NC2N1)=CNC3C(O)C(O)C=C3 tautomer #99
N=C1NC(O)=C2C(=CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #100
N=c1[nH]c(O)c2C(CNc2n1)=CNC3C(O)C(O)C=C3 tautomer #101
NC1=NC(O)=C2C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #102
NC1=NC(O)=C2C(=CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #103
NC1=NC(O)=C2C(C=NC2N1)=CNC3C(O)C(O)C=C3 tautomer #104
N=C1NC(O)=C2C(CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #105
N=c1[nH]c(O)c-2c(cnc2[nH]1)CNC3C(O)C(O)C=C3 tautomer #106
N=C1NC(O)=C2C(CN=C2N1)=CNC3C(O)C(O)C=C3 tautomer #107
NC1=NC(O)=C2C(CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #108
NC1=NC(O)=C2C(CN=C2N1)=CNC3C(O)C(O)C=C3 tautomer #109
N=C1N=C(O)C2C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #110
N=C1N=C(O)C2=C(C=NC2N1)CNC3C(O)C(O)C=C3 tautomer #111
N=C1N=C(O)C2=C(CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #112
N=C1N=C(O)C2C(CNC2=N1)C=NC3C(O)C(O)C=C3 tautomer #113
N=C1N=C(O)C2=C(CNC2=N1)CNC3C(O)C(O)C=C3 tautomer #114
NC=1N=C(O)C2=C(CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #115
NC=1N=C(O)C2=C(C=NC2N1)CNC3C(O)C(O)C=C3 tautomer #116
NC=1N=C(O)C2C(C=NC2N1)C=NC3C(O)C(O)C=C3 tautomer #117
N=C1N=C(O)C2C(C=NC2=N1)CNC3C(O)C(O)C=C3 tautomer #118
N=C1N=C(O)C2C(=CNC2N1)C=NC3C(O)C(O)C=C3 tautomer #119
N=C1N=C(O)C2C(C=NC2N1)=CNC3C(O)C(O)C=C3 tautomer #120
N=C1N=C(O)C2C(=CNC2=N1)CNC3C(O)C(O)C=C3 tautomer #121
N=C1N=C(O)C2C(CNC2=N1)=CNC3C(O)C(O)C=C3 tautomer #122
NC=1N=C(O)C2C(C=NC2N1)=CNC3C(O)C(O)C=C3 tautomer #123
N=c1nc(O)c2C(C=Nc2[nH]1)CNC3C(O)C(O)C=C3 tautomer #124
N=c1nc(O)c2C(CNc2[nH]1)C=NC3C(O)C(O)C=C3 tautomer #125
N=c1nc(O)c2C(CNc2[nH]1)=CNC3C(O)C(O)C=C3 tautomer #126
N=C1N=C(O)C2C(CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #127
N=c1nc(O)c2=C(CN=c2[nH]1)CNC3C(O)C(O)C=C3 tautomer #128
NC=1N=C(O)C2C(CN=C2N1)C=NC3C(O)C(O)C=C3 tautomer #129
N=C1N=C(O)C2C(=CN=C2N1)CNC3C(O)C(O)C=C3 tautomer #130
N=C1N=C(O)C2C(CN=C2N1)=CNC3C(O)C(O)C=C3 tautomer #131
NC=1N=C(O)C2C(CN=C2N1)=CNC3C(O)C(O)C=C3 tautomer #132
NC=1N=C(O)C2C(=CN=C2N1)CNC3C(O)C(O)C=C3 tautomer #133

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
Qbase Qbase Qbase

* 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 mass277.1175
Average mass277.279
[M+H]+278.1253
Product ions146
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.

Chemical groups contained

TypeSubtype
otherqueuosine

Reactions producing queuine

Name
Q:Qbase

Reactions starting from queuine

Name
Qbase:Q

Last modification of this entry: Sept. 29, 2021


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