Compound: queuine
SMILES: O=c1[nH]c(nc2c1c(c[nH]2)CN[C@H]3C=C[C@@H]([C@@H]3O)O)N
InChIKey: WYROLENTHWJFLR-ACLDMZEESA-N
Synonyms: queuine, 72496-59-4, base Q, Q Base, DAK6EYX2BZ, 7-(3,4-trans-4,5-cis-dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanine, 2-amino-5-[[[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino]methyl]-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, CHEBI:17433, DTXSID20895854, 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-, 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, 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))-, 2-amino-5-((((1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl)amino)methyl)-3,7-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, RefChem:178134, DTXCID201325352, 5-((((1R,4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl)amino)methyl)-2-imino-1H,2H,3H,4H,7H-pyrrolo(2,3-d)pyrimidin-4-one, Queuine Hydrochloride, 85549-16-2, 69565-92-0, 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-dihydroxy-2-cyclopenten-1-yl]amino]methyl]-1,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one Dihydrochloride; [1S-(1a,4ss,5ss)]-2-Amino-5-[[(4,5- dihydroxy-2-cyclopenten-1-yl)amino]methyl]-1,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one Hydrochloride;, CID 114881, UNII-DAK6EYX2BZ, SCHEMBL93906, 2-amino-5-[[[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino]methyl]-1,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, orb1985373, SCHEMBL15972267, GLXC-27316, HY-N10574, AKOS040753672, AT39289, DB14732, NQ177252, CS-0612528, NS00126521, C01449, Q424797, 2-Amino-5-((((1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl)amino)methyl)-1H-pyrrolo[2,3-d]pyrimidin-4(7H)-one, 2-amino-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-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]-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one hydrochloride, 4H-PYRROLO(2,3-D)PYRIMIDIN-4-ONE, 2-AMINO-5-(((4,5-DIHYDROXY-2-CYCLOPENTEN-1-YL)AMINO)METHYL)-1,7-DIHYDRO-, (1S-(1.ALPHA.,4.BETA.,5.BETA.))-
Theoretical properties:
molecular_formula: C12H15N5O3
molecular_weight: 277.28 g/mol
exact_mass: 277.11748936 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 3
heavy_atom_count: 20
topological_polar_surface_area: 136 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Queuine is a pyrrolopyrimidine. It has a role as an Escherichia coli metabolite. It is a conjugate base of a queuine(1+).
wikipedia: Queuine () (Q) is a hypermodified nucleobase found in the first (or wobble) position of the anticodon of tRNAs specific for Asn, Asp, His, and Tyr, in most eukaryotes and prokaryotes. Because it is utilized by all eukaryotes but produced exclusively by bacteria, it is a putative vitamin.
The nucleoside of queuine is queuosine.  Queuine is not found in the tRNA of archaea; however, a related 7-deazaguanine derivative, the nucleoside of which is archaeosine, occurs in different tRNA position, the dihydrouridine loop, and in tRNAs with more specificities.