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Queuine

CAT: 0804-HY-N10574-03Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N10574-03Size:10 mg
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Description
Queuine is a selective substrate for tRNA guanine transglycosylase (TGT) and can be incorporated into eukaryotic tRNA. Queuine promotes tRNA modification, affecting mitochondrial function and Warburg metabolic phenotype. If Queuine is deficient, aerobic glycolysis can be enhanced, oxidative phosphorylation can be inhibited, and Warburg metabolism can be promoted, accompanied by increased ammonia and lactate production and increased lactate dehydrogenase activity. Queuine can be used for autoimmune diseases (such as experimental models of multiple sclerosis) and cancer metabolic regulation, and its deficiency is associated with low tRNA modification in tumor cells[1][2][3].
CAS Number
72496-59-4
UNSPSC
12352005
Target
Bacterial
Type
Natural Products
Related Pathways
Anti-infection
Field of Research
Cancer; Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/queuine.html
Purity
99.74
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O[C@@H]([C@H](C=C1)O)[C@H]1NCC2=CNC(NC(N)=N3)=C2C3=O
Molecular Formula
C12H15N5O3
Molecular Weight
277.28
References & Citations
[1]Yifeng Yuan, et al. Discovery of novel bacterial queuine salvage enzymes and pathways in human pathogens. Proc Natl Acad Sci U S A. 2019 Sep 17;116 (38) :19126-19135.|[2]Hayes P, et al. Queuine Micronutrient Deficiency Promotes Warburg Metabolism and Reversal of the Mitochondrial ATP Synthase in Hela Cells. Nutrients. 2020 Mar 24;12 (3) :871.|[3]Varghese S, et al. In vivo modification of tRNA with an artificial nucleobase leads to full disease remission in an animal model of multiple sclerosis. Nucleic Acids Res. 2017 Feb 28;45 (4) :2029-2039.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Queuine

Queuine is a pyrrolopyrimidine. It has a role as an Escherichia coli metabolite. It is a conjugate base of a queuine(1+).

CAS Number72496-59-4
PubChem CID135398670
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
Molecular FormulaC12H15N5O3
Molecular Weight277.28
XLogP-2.4
Topological Polar Surface Area136
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Heavy Atom Count20
Formal Charge0
Complexity466
SMILES
C1=C[C@@H]([C@@H]([C@H]1NCC2=CNC3=C2C(=O)NC(=N3)N)O)O
InChI
InChI=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
InChIKey
WYROLENTHWJFLR-ACLDMZEESA-N
Chemical Structure
2D Structure
2D structure of Queuine
CAS: 72496-59-4
CID: 135398670
Formula: C12H15N5O3
MW: 277.28
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight277.28
XLogP3-2.4
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass277.11748936
Monoisotopic Mass277.11748936
Topological Polar Surface Area136 Ų
Heavy Atom Count20
Formal Charge0
Complexity466
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
T34221-01Queuine
TRC-Q525000-2.5MGQueuine Hydrochloride
GTR19236140-01Queuine dihydrochloride
489853QTRT1 (Queuine tRNA-Ribosyltransferase, Queuine tRNA-Ribosyltransferase 1)
489855QTRTD1 (Queuine tRNA-Ribosyltransferase Subunit QTRTD1, Queuine tRNA-Ribosyltransferase Domain Containing 1)
MBS1362858-01Recombinant Rat Queuine tRNA-ribosyltransferase (Qtrt1)
MBS1329292-01Recombinant Human Queuine tRNA-ribosyltransferase (QTRT1)
MBS140664-01Recombinant Human Queuine TRNA-Ribosyltransferase 1
MBS1324663-01Recombinant Mouse Queuine tRNA-ribosyltransferase (Qtrt1)
rAP-2042Queuine TRNA-Ribosyltransferase 1 Human Recombinant

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