L-Threonylcarbamoyladenylate (ECMDB23796) (M2MDB004367)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (437)
Record Information
Version2.0
Creation Date2015-06-04 15:18:54 -0600
Update Date2015-08-05 16:22:04 -0600
Secondary Accession Numbers
  • ECMDB23796
Identification
Name:L-Threonylcarbamoyladenylate
DescriptionA threonine derivative that is L-threonine in which one of the amino hydrogens is substituted by and adenyloxycarbonyl group
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • L-Threonylcarbamoyl-AMP
  • L-Threonylcarbamoyladenylic acid
  • N-(Adenyloxycarbonyl)-L-threnine
  • TC-AMP
Chemical Formula:C15H21N6O11P
Weight:Average: 492.3346
Monoisotopic: 492.100592056
InChI Key:GHLUPQUHEIJRCU-DWVDDHQFSA-N
InChI:InChI=1S/C15H21N6O11P/c1-5(22)7(14(25)26)20-15(27)32-33(28,29)30-2-6-9(23)10(24)13(31-6)21-4-19-8-11(16)17-3-18-12(8)21/h3-7,9-10,13,22-24H,2H2,1H3,(H,20,27)(H,25,26)(H,28,29)(H2,16,17,18)/t5-,6-,7+,9-,10-,13-/m1/s1
CAS number:Not Available
IUPAC Name:(2S,3R)-2-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)methylidene}amino)-3-hydroxybutanoic acid
Traditional IUPAC Name:(2S,3R)-2-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid
SMILES:[H][C@](C)(O)[C@]([H])(N=C(O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Alpha-amino acid or derivatives
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Beta-hydroxy acid
  • Sugar acid
  • Monoalkyl phosphate
  • Imidolactam
  • Pyrimidine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Monosaccharide
  • Tetrahydrofuran
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Amino acid or derivatives
  • Carbonic acid derivative
  • Amino acid
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Amine
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.7 g/LALOGPS
logP-2ALOGPS
logP-4.2ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)2.58ChemAxon
pKa (Strongest Basic)4.87ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area265.19 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity103.86 m³·mol⁻¹ChemAxon
Polarizability42.07 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
L-Threonylcarbamoyladenylate <> Adenosine monophosphate
L-Threonine + Adenosine triphosphate + Hydrogen carbonate <> L-Threonylcarbamoyladenylate + Pyrophosphate + Water
L-Threonine + Adenosine triphosphate + Hydrogen carbonate <> L-Threonylcarbamoyladenylate + Pyrophosphate + Water
L-Threonylcarbamoyladenylate <> Adenosine monophosphate
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_22) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0912200000-3c41643a52fce04f02a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-4723c3a7dcbf79f77c3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2900000000-ef8f710b39e30b915a2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00c0-3938700000-b577cc9ad622d46321a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3912100000-9bf68d4a5ccdb3cfb250View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4910000000-7a48959fa6b71f587873View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID73687
HMDB IDNot Available
Pubchem Compound ID56835784
Kegg IDC20641
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. tRNA N6-adenosine threonylcarbamoyltransferase
General function:
threonylcarbamoyladenosine biosynthetic process
Specific function:
Required for the formation of a threonylcarbamoyl group on adenosine at position 37 (t(6)A37) in tRNAs that read codons beginning with adenine. Is probably involved in the transfer of the threonylcarbamoyl moiety of threonylcarbamoyl-AMP (TC-AMP) to the N6 group of A37, together with TsaE and TsaB. TsaD likely plays a direct catalytic role in this reaction. May also be involved in the metabolism of glycated proteins, but does not show sialoglycoprotease activity against glycophorin A.
Gene Name:
tsaD
Uniprot ID:
P05852
Molecular weight:
36008
Reactions
L-threonylcarbamoyladenylate + adenine(37) in tRNA = AMP + N(6)-L-threonylcarbamoyladenine(37) in tRNA
Protein Details
2. Threonylcarbamoyl-AMP synthase
General function:
threonylcarbamoyladenosine biosynthetic process
Specific function:
Required for the formation of a threonylcarbamoyl group on adenosine at position 37 (t(6)A37) in tRNAs that read codons beginning with adenine. Catalyzes the conversion of L-threonine, bicarbonate/CO(2) and ATP to give threonylcarbamoyl-AMP (TC-AMP) as the acyladenylate intermediate, with the release of pyrophosphate. Is also able to catalyze the reverse reaction in vitro, i.e. the formation of ATP from TC-AMP and PPi. Shows higher affinity for the full-length tRNA(Thr) lacking only the t(6)A37 modification than for its fully modified counterpart. Could also be required for the maturation of 16S rRNA. Binds to double-stranded RNA but does not interact tightly with either of the ribosomal subunits, or the 70S particles.
Gene Name:
tsaC
Uniprot ID:
P45748
Molecular weight:
20767
Reactions
L-threonine + ATP + bicarbonate = L-threonylcarbamoyladenylate + diphosphate + H(2)O