Summary

Full name7-aminomethyl-7-carbaguanine
IUPAC name2-amino-5-(aminomethyl)-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one
Short namepreQ1base
MODOMICS code101000G
Synonyms
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
2-amino-5-(aminomethyl)-1,7-dihydro-4h-pyrrolo[2,3-d]pyrimidin-4-one
2-amino-5-(aminomethyl)-1,7-dihydropyrrolo[2,3-d]pyrimidin-4-one
2-amino-5-(aminomethyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
2-amino-5-(aminomethyl)-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one
2-Amino-5-(aminomethyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one
2-Amino-5-(aminomethyl)pyrrolo[2,3-d]pyrimidin-4(3H)-one
69251-45-2
7-Aminomethyl-7-carbaguanine
7-aminomethyl-7-deazaguanine
7-DEAZA-7-AMINOMETHYL-GUANINE
AC1L18MX
C16675
CHEBI:45126
CHEMBL1235432
CID171
CTK7E3986
DB03304
HNG
NS00069406
preQ1
PRF
Q27120591
QEI
queuine
SCHEMBL166747
SCHEMBL20206657
ZINC3869370

Nature of the modified residueNatural
RNAMods code
Residue unique ID61
Found in RNAYes
Enzymes QueF (Escherichia coli)
QueF (Bacillus subtilis)
Found in phylogenyEubacteria

Chemical information

Sum formulaC7H9N5O
Type of moietybase
Degeneracynot applicable
SMILESNc1[nH]c(=O)c2c([nH]cc2CN)n1
logP0.5736
TPSA113.58
Number of atoms13
Number of Hydrogen Bond Acceptors 1 (HBA1)4
Number of Hydrogen Bond Acceptors 2 (HBA2)4
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand HNG
PDB exact match , link to the most similar ligand PRF
HMDB (Human Metabolome Database) exact match HMDB0011690
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0011690
InChIInChI=1S/C7H9N5O/c8-1-3-2-10-5-4(3)6(13)12-7(9)11-5/h2H,1,8H2,(H4,9,10,11,12,13)
InChIKeyMEYMBLGOKYDGLZ-UHFFFAOYSA-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([nH]cc2C=N)N1 tautomer #0
N=c1[nH]c(=O)c2c([nH]cc2CN)[nH]1 tautomer #1
NC=1NC(O)c2c([nH]cc2C=N)N1 tautomer #2
Nc1nc(O)c2c([nH]cc2CN)n1 tautomer #3
NC1=NC(O)c2c([nH]cc2C=N)N1 tautomer #4
Nc1nc(O)c2-c(ncc2CN)[nH]1 tautomer #5
Nc1[nH]c(O)c2-c(ncc2CN)n1 tautomer #6
Nc1nc(=O)c2c([nH]cc2CN)[nH]1 tautomer #7
Nc1[nH]c(=O)c2c([nH]cc2CN)n1 tautomer #8
Nc1nc(O)c2c(NCC2C=N)n1 tautomer #9
Nc1nc(O)c2c(N=CC2CN)n1 tautomer #10
Nc1nc(O)c2c(NCC2=CN)n1 tautomer #11
N=c1[nH]c(O)c2c([nH]cc2CN)n1 tautomer #12
N=C1NC(=O)C2C(N=CC2C=N)N1 tautomer #13
N=C1NC(=O)C=2C(N=CC2CN)N1 tautomer #14
N=C1NC(O)C=2C(N=CC2C=N)N1 tautomer #15
N=C1NC(=O)C=2C(NCC2C=N)N1 tautomer #16
N=C1NC(O)C=2C(N=CC2CN)=N1 tautomer #17
N=C1NC(=O)C2C(NCC2C=N)=N1 tautomer #18
N=C1NC(O)C=2C(NCC2C=N)=N1 tautomer #19
N=C1NC(=O)C=2C(NCC2CN)=N1 tautomer #20
N=C1NC(=O)C2C(N=CC2CN)=N1 tautomer #21
NC1=NC(O)C2C(N=CC2C=N)=N1 tautomer #22
NC=1NC(=O)C=2C(NCC2C=N)N1 tautomer #23
NC=1NC(O)C=2C(=NCC2C=N)N1 tautomer #24
Nc1[nH]c(=O)c=2c(=NCC2CN)n1 tautomer #25
NC=1NC(=O)C=2C(N=CC2CN)N1 tautomer #26
NC=1NC(=O)C2C(N=CC2C=N)N1 tautomer #27
NC=1NC(O)C=2C(N=CC2C=N)N1 tautomer #28
N=C1NC(=O)C2C(NC=C2C=N)N1 tautomer #29
N=C1NC(=O)C2C(N=CC2=CN)N1 tautomer #30
N=C1NC(=O)C2C(NC=C2CN)=N1 tautomer #31
N=C1NC(=O)C2C(NCC2=CN)=N1 tautomer #32
N=C1NC(O)C2=C(N=CC2C=N)N1 tautomer #33
N=c1[nH]c(=O)c2c(NCC2C=N)[nH]1 tautomer #34
NC1=NC(O)C2C(N=CC2=CN)=N1 tautomer #35
NC1=NC(O)C2C(NC=C2C=N)=N1 tautomer #36
Nc1[nH]c(=O)c2c(NCC2C=N)n1 tautomer #37
NC=1NC(O)C2=C(N=CC2C=N)N1 tautomer #38
NC=1NC(=O)C2C(N=CC2=CN)N1 tautomer #39
NC=1NC(=O)C2C(NC=C2C=N)N1 tautomer #40
Nc1nc(O)c=2c(=NCC2CN)n1 tautomer #41
N=C1NC(O)C2=C(N=CC2=CN)N1 tautomer #42
N=c1[nH]c(=O)c2c(NCC2=CN)[nH]1 tautomer #43
N=c1[nH]c(=O)c2c(N=CC2CN)[nH]1 tautomer #44
Nc1[nH]c(=O)c2c(NCC2=CN)n1 tautomer #45
NC=1NC(O)C2=C(N=CC2=CN)N1 tautomer #46
Nc1nc(O)c2c(NCC2C=N)n1 tautomer #47
Nc1nc(O)c2c([nH]cc2CN)n1 tautomer #48
NC1=NC(=O)C2C(N=CC2C=N)N1 tautomer #49
NC1=NC(=O)C=2C(N=CC2CN)N1 tautomer #50
NC1=NC(O)C=2C(N=CC2C=N)N1 tautomer #51
NC1=NC(=O)C=2C(NCC2C=N)N1 tautomer #52
NC1=NC(O)C=2C(N=CC2CN)=N1 tautomer #53
NC1=NC(=O)C2C(NCC2C=N)=N1 tautomer #54
NC1=NC(O)C=2C(NCC2C=N)=N1 tautomer #55
NC1=NC(=O)C=2C(NCC2CN)=N1 tautomer #56
N=C1NC(=O)C2C(=NCC2C=N)N1 tautomer #57
N=C1NC(O)C=2C(=NCC2C=N)N1 tautomer #58
N=c1[nH]c(=O)c=2c(=NCC2CN)[nH]1 tautomer #59
NC1=NC(=O)C2C(N=CC2CN)=N1 tautomer #60
N=C1NC(O)C2C(N=CC2C=N)=N1 tautomer #61
Nc1nc(O)c2c(NCC2=CN)n1 tautomer #62
NC1=NC(=O)C2C(NC=C2C=N)N1 tautomer #63
NC1=NC(=O)C2C(N=CC2=CN)N1 tautomer #64
NC1=NC(=O)C2C(NC=C2CN)=N1 tautomer #65
NC1=NC(=O)C2C(NCC2=CN)=N1 tautomer #66
NC1=NC(O)C2=C(N=CC2C=N)N1 tautomer #67
N=C1NC(=O)C2C(=NC=C2CN)N1 tautomer #68
N=C1NC(=O)C2C(=NCC2=CN)N1 tautomer #69
N=C1NC(O)C2C(N=CC2=CN)=N1 tautomer #70
N=C1NC(O)C2C(NC=C2C=N)=N1 tautomer #71
Nc1nc(=O)c2c(NCC2C=N)[nH]1 tautomer #72
NC1=NC(O)C2=C(N=CC2=CN)N1 tautomer #73
Nc1nc(=O)c2c(N=CC2CN)[nH]1 tautomer #74
Nc1nc(=O)c2c(NCC2=CN)[nH]1 tautomer #75
NC1=NC(=O)C2C(=NCC2C=N)N1 tautomer #76
NC1=NC(O)C=2C(=NCC2C=N)N1 tautomer #77
Nc1nc(=O)c=2c(=NCC2CN)[nH]1 tautomer #78
NC=1NC(=O)C2C(=NC=C2CN)N1 tautomer #79
NC=1NC(=O)C2C(=NCC2C=N)N1 tautomer #80
N=c1nc(O)c2c([nH]cc2CN)[nH]1 tautomer #81
NC1=NC(=O)C2C(=NC=C2CN)N1 tautomer #82
NC1=NC(=O)C2C(=NCC2=CN)N1 tautomer #83
Nc1[nH]c(=O)c2c(N=CC2CN)n1 tautomer #84
NC=1NC(=O)C2C(=NCC2=CN)N1 tautomer #85
NC=1NC(O)=C2C(=NCC2C=N)N1 tautomer #86
N=C1NC(O)=C2C(N=CC2C=N)N1 tautomer #87
N=c1[nH]c(O)c2c(NCC2C=N)n1 tautomer #88
N=c1[nH]c(O)c2c(N=CC2CN)n1 tautomer #89
NC=1NC(O)=C2C(=NCC2=CN)N1 tautomer #90
NC=1NC(O)=C2C(N=CC2C=N)N1 tautomer #91
Nc1nc(O)c2c(N=CC2CN)n1 tautomer #92
N=C1NC(O)=C2C(N=CC2=CN)N1 tautomer #93
NC=1NC(O)=C2C(N=CC2=CN)N1 tautomer #94
NC=1NC(O)=C2C(NC=C2C=N)N1 tautomer #95
N=C1NC(O)=C2C(NC=C2C=N)N1 tautomer #96
N=c1[nH]c(O)c2c(NCC2=CN)n1 tautomer #97
NC1=NC(O)=C2C(N=CC2C=N)N1 tautomer #98
NC1=NC(O)=C2C(NC=C2C=N)N1 tautomer #99
NC1=NC(O)=C2C(N=CC2=CN)N1 tautomer #100
N=C1NC(O)=C2C(=NCC2C=N)N1 tautomer #101
N=c1[nH]c(O)c2-c(ncc2CN)[nH]1 tautomer #102
N=C1NC(O)=C2C(=NCC2=CN)N1 tautomer #103
NC1=NC(O)=C2C(=NCC2C=N)N1 tautomer #104
NC1=NC(O)=C2C(=NCC2=CN)N1 tautomer #105
N=C1N=C(O)C2C(N=CC2C=N)N1 tautomer #106
N=C1N=C(O)C=2C(N=CC2CN)N1 tautomer #107
N=C1N=C(O)C=2C(NCC2C=N)N1 tautomer #108
N=C1N=C(O)C2C(NCC2C=N)=N1 tautomer #109
N=C1N=C(O)C=2C(NCC2CN)=N1 tautomer #110
N=C1N=C(O)C2C(N=CC2CN)=N1 tautomer #111
NC=1N=C(O)C=2C(NCC2C=N)N1 tautomer #112
NC=1N=C(O)C=2C(N=CC2CN)N1 tautomer #113
NC=1N=C(O)C2C(N=CC2C=N)N1 tautomer #114
N=C1N=C(O)C2C(NC=C2C=N)N1 tautomer #115
N=C1N=C(O)C2C(N=CC2=CN)N1 tautomer #116
N=C1N=C(O)C2C(NC=C2CN)=N1 tautomer #117
N=C1N=C(O)C2C(NCC2=CN)=N1 tautomer #118
NC=1N=C(O)C2C(N=CC2=CN)N1 tautomer #119
NC=1N=C(O)C2C(NC=C2C=N)N1 tautomer #120
N=c1nc(O)c2c(NCC2C=N)[nH]1 tautomer #121
N=c1nc(O)c2c(N=CC2CN)[nH]1 tautomer #122
N=c1nc(O)c2c(NCC2=CN)[nH]1 tautomer #123
N=C1N=C(O)C2C(=NCC2C=N)N1 tautomer #124
N=c1nc(O)c=2c(=NCC2CN)[nH]1 tautomer #125
NC=1N=C(O)C2C(=NCC2C=N)N1 tautomer #126
N=C1N=C(O)C2C(=NC=C2CN)N1 tautomer #127
N=C1N=C(O)C2C(=NCC2=CN)N1 tautomer #128
NC=1N=C(O)C2C(=NCC2=CN)N1 tautomer #129
NC=1N=C(O)C2C(=NC=C2CN)N1 tautomer #130

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
preQ1base preQ1base preQ1base

* 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 mass179.0807
Average mass179.179
[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.

Chemical groups contained

TypeSubtype
methyl groupmethyl at aromatic C
otherprimary amine

Reactions producing 7-aminomethyl-7-carbaguanine

Name
preQ0base:preQ1base

Reactions starting from 7-aminomethyl-7-carbaguanine

Name
preQ1base:preQ1

Last modification of this entry: Sept. 29, 2021


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