Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB003576
Identification
Name: epoxyqueuosine
Description:Epoxyqueuosine is an intermediate in queosine biosynthesis. Queuosine is an important 7-deazapurine-modified nucleoside that is present in certain tRNAs in bacteria and most eukaryotes. Eposyqueosiine is a subsstrate for Epoxyqueuosine reductase catalyzes the final step in the de novo synthesis of queuosine, the anticodon loop modification found in tRNA(Asp), tRNA(Asn), tRNA(His), and tRNA(Tyr)
Structure
Thumb
Synonyms:
  • 2-amino-7-(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl-5-(3,4-dihydroxy-6-oxabicyclo3.1.0hexan-2-yl)aminomethyl-1H-pyrrolo2,3-dpyrimidin-4-one
Chemical Formula: C17H23N5O8
Average Molecular Weight: 425.3932
Monoisotopic Molecular Weight: 425.154662737
InChI Key: RRCFLRBBBFZLSB-MPMHWICOSA-N
InChI:InChI=1S/C17H23N5O8/c18-17-20-14-6(15(28)21-17)4(1-19-7-9(25)10(26)13-12(7)30-13)2-22(14)16-11(27)8(24)5(3-23)29-16/h2,5,7-13,16,19,23-27H,1,3H2,(H3,18,20,21,28)/t5-,7?,8-,9?,10?,11-,12?,13?,16-/m1/s1
CAS number: Not Available
IUPAC Name:4-[({7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]-6-oxabicyclo[3.1.0]hexane-2,3-diol
Traditional IUPAC Name: 4-[({7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-imino-1H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]-6-oxabicyclo[3.1.0]hexane-2,3-diol
SMILES:[H]C12OC1([H])C([H])(NCC1=CN(C3=C1C(O)=NC(=N)N3)[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@@]1([H])O)C([H])(O)C2([H])O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrrolopyrimidine nucleosides and nucleotides. These are nucleoside derivatives containing a ribose derivative which is n-glycosylated to a pyrrolopyrimidine. Also called deazapurine nucleosides, they are analogs of purine nucleosides with the N atom of the purine being replaced by a C atom at position 7.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Pyrrolopyrimidine nucleosides and nucleotides
Sub ClassNot Available
Direct Parent Pyrrolopyrimidine nucleosides and nucleotides
Alternative Parents
Substituents
  • Pyrrolopyrimidine ribonucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Pyrrolopyrimidine
  • Hydroxypyrimidine
  • Aralkylamine
  • Substituted pyrrole
  • Pyrimidine
  • Oxane
  • Monosaccharide
  • Heteroaromatic compound
  • Pyrrole
  • Oxolane
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Ether
  • Oxirane
  • Secondary aliphatic amine
  • Dialkyl ether
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility11.2 mg/mLALOGPS
logP-2ALOGPS
logP-3.5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8.12ChemAxon
pKa (Strongest Basic)7.19ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area208.34 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity108.67 m3·mol-1ChemAxon
Polarizability41.18 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0190500000-4bf2c623937e408d8c12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01r6-1390000000-161e99fd241fb8a0b070View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02bf-2970000000-f7be51e3d3034bcffb3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-0352900000-a85259aa6433a85435aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0391000000-676e48ba02c1cf255bc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0960000000-4b96461d04f006aa653aView in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID3035951
Kegg IDNot Available
ChemSpider ID2300068
Wikipedia IDNot Available
BioCyc IDNot Available